Abstract
The article contains sections titled:
1. |
Introduction and History |
2. |
Properties |
2.1. |
Physical Properties and Structure |
2.2. |
Chemical Properties |
2.3. |
Important Amino Acids |
2.3.1. |
Proteinogenic Amino Acids |
2.3.2. |
Other Important Amino Acids |
3. |
Industrial Production of Amino Acids |
3.1. |
General Methods |
3.2. |
Production of Specific Amino Acids |
3.2.1. |
l-Alanine |
3.2.2. |
l-Arginine |
3.2.3. |
l-Aspartic Acid and Asparagine |
3.2.4. |
l-Cystine and l-Cysteine |
3.2.5. |
l-Glutamic Acid |
3.2.6. |
l-Glutamine |
3.2.7. |
l-Histidine |
3.2.8. |
l-Hydroxyproline |
3.2.9. |
l-Isoleucine |
3.2.10. |
l-Leucine |
3.2.11. |
l-Lysine |
3.2.12. |
d,l-Methionine and l-Methionine |
3.2.13. |
l-Phenylalanine |
3.2.14. |
l-Proline |
3.2.15. |
l-Serine |
3.2.16. |
l-Threonine |
3.2.17. |
l-Tryptophan |
3.2.18. |
l-Tyrosine |
3.2.19. |
l-Valine |
4. |
Biochemical and Physiological Significance |
5. |
Uses |
5.1. |
Human Nutrition |
5.1.1. |
Supplementation |
5.1.2. |
Flavorings, Taste Enhancers, and Sweeteners |
5.1.3. |
Other Uses in Foodstuff Technology |
5.2. |
Animal Nutrition |
5.3. |
Pharmaceuticals |
5.3.1. |
Nutritive Agents |
5.3.2. |
Therapeutic Agents |
5.4. |
Cosmetics |
5.5. |
Agrochemicals |
5.5.1. |
Herbicides |
5.5.2. |
Fungicides |
5.5.3. |
Insecticides |
5.5.4. |
Plant Growth Regulators |
5.6. |
Industrial Uses |
6. |
Chemical Analysis |
7. |
Economic Significance |
8. |
Toxicology |
General References
- 1 J. P. Greenstein, M. Winitz: Chemistry of the Amino Acids, vol. 1, 2, and 3, J. Wiley & Sons, New York–London 1961.
- 2
A. Meister:
Biochemistry of the Amino Acids,
2nd ed.,
vol. 1,
Academic Press,
New York
1965.
10.1016/B978-0-12-395523-4.50008-3 Google Scholar
- 3 I. Wagner, H. Musso: “Neue natürliche Aminosäuren” Angew. Chem. 95 (1983), 827–920; Angew. Chem. Int. Ed. Eng. 22 (1983) 816 (review of the literature since 1956).
- 4 IUPAC and IUB Joint Commission on Biochemical Nomenclature, Pure Appl. Chem., 56 (1984) 595.
- 5 G. C. Barrett (ed.): Amino Acid Derivatives, Oxford University Press, Oxford 1999.
- 6 Houben-Weyl, E16d, 1992; Science and Synthesis, v. 26, 2004, p. 1255.
- 7 S. E. Wolkenberg, R. M. Garbaccio, Science of Synthesis 20a (2006) 385.
- 8 Th. Wieland et al.: Methoden zur Herstellung und Umwandlung von Aminosäuren und Derivaten, Houben-Weyl, 11/2.
- 9 H. D. Jakubke, H. Jeschkeit: Aminosäuren, Peptide, Proteine, Verlag Chemie, Weinheim, Germany 1982.
- 10 B. Weinstein (ed.): Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol. 1–5, Marcel Dekker, New York 1971 –1978.
- 11 D. Barton, W. D. Ollis: Comprehensive Organic Chemistry, vol. 2, Chap. 9.6, p. 815; vol. 5 Pergamon Press, New York 1979.
- 12 G. Krügers: Aminocarbonsäuren in: Methodicum Chimicum, vol. 6, p. 611.
- 13 E. Wünsch: Synthese von Peptiden, Houben-Weyl, 15/1 and 15/2.
Specific References
- 14 S. K. Bhattacharyya, A. B. Banerjee, Folia Microbiol. (Prague) 19 (1974) 43.
- 15 T. Robinson, Life Sci. 19 (1976) 1097.
- 16 R. E. Dickerson, Spektrum der Wissenschaften 1979, no. 9, 98.
- 17
R. S. Cahn,
C. Ingold,
V. Prelog,
Angew. Chem.
78
(1966)
413;
10.1002/ange.19660780803 Google ScholarAngew. Chem. Int. Ed. Engl. 5 (1966) 385, 511.
- 18 K. Lübke, E. Schröder, G. Kloss: Chemie und Biochemie der Aminosäuren, Peptide und Proteine, vol. I and II, Thieme Verlag, Stuttgart 1975.
- 19 A. Kleemann, Chem. Ztg. 106 (1982) 151–167.
- 20 K. H. Drauz, A. Kleemann, J. Martens, Angew. Chem. 94 (1982) 590; Angew. Chem. Int. Ed. Engl. 21 (1982) 584.
- 21 A. Berkessel, H.w Gröger: Asymmetric Organocatalysis, Wiley-VCH, Weinheim 2005.
- 22 Drugs of the Future 23 (1998) 1057.
- 23 R. P. Nargund, A. A. Patchett, M. A. Bach, M. G. Murphy, R. G. Smith, J. Med. Chem. 41 (1998) 3103.
- 24
Drugs of the Future
19
(1994)
111.
10.1358/dof.1994.019.02.238213 Google Scholar
- 25 H. J. Federsel, Chirality 15 (2003) 128.
- 26 A. Müller, E. Busker, J. Engel, B. Kutscher, M. Bernd, A. V. Schally, Int. J. Peptide Prot. Res. 43 (1994) 264.
- 27 Europ. Pat. Appl. EP 0 530 167 A 1, 1993 (B. Atrash, D. M. Jones, M. Szelke).
- 28 Drugs of the Future 22 (1997) 371.
- 29
Drugs of the Future
17
(1992)
551.
10.1358/dof.1992.017.07.177837 Google Scholar
- 30 Drugs of the Future 23 (1998) 751.
- 31 J. A. Robl et al., J. Med. Chem. 40 (1997) 1570.
- 32 S. Budavari (ed.): The Merck Index, 12th ed., Merck & Co., Inc., Whitehouse Station, NJ 1996, p. 97.
- 33 A. S. Bommarius, M. Schwarm, K. Stingl, M. Kottenhahn, K. Huthmacher, K. Drauz, Tetrahedron: Asymmetry 6 (1995) 2851.
- 34
Drugs of the Future
21
(1996)
1022.
10.1358/dof.1996.021.10.375535 Google Scholar
- 35 Drugs of the Future 23 (1998) 1057.
- 36
Drugs of the Future
19
(1994)
985.
10.1358/dof.1994.019.11.268131 Google Scholar
- 37 J. F. Atkins, R. Gesteland, Science 296 (2002) 1409.
- 38
Drugs of the Future
18
(1993)
503.
10.1358/dof.1993.018.06.209238 Google Scholar
- 39 Drugs of the Future 23 (1998) 1057.
- 40 Drugs of the Future 22 (1997) 260.
- 41 Drugs of the Future 22 (1997) 371.
- 42 S. Budavari (ed.): The Merck Index, 12th ed., Merck & Co., Inc., Whitehouse Station, NJ 1996, p. 99.
- 43
Drugs of the Future
14
(1989)
767.
10.1358/dof.1989.014.08.103349 Google Scholar
- 44
Drugs of the Future
21
(1996)
600.
10.1358/dof.1996.021.06.361961 Google Scholar
- 45 Drugs of the Future 18 (1993) 1129.
- 46 Drugs of the Future 22 (1997) 221.
- 47 Drugs of the Future 23 (1998) 1057.
- 48 V. N. Gladyshev, D. L. Hatfield, J. Biomed. Sci. 6 (1999) 151.
- 49 G. N. Schrauzer, J. Nutrition 130 (2000) 1653.
- 50 Drugs of the Future 19 (1994) 988.
- 51 R. Meister (ed.): Farm Chemical Handbook 1990, Meister Publishing Co., Willoughby, OH 1990, p. C136.
- 52 W. Leuchtenberger, K. Huthmacher, K. Drauz, Appl. Microbiol. Biotech. 69 (2005) 1.
- 53 T. Hermann, J. Biotechnol. 104 (2003) 155.
- 54 M. Breuer et al., Angew. Chem. Int. Ed. 43 (2004) 788.
- 55 J. Jones: Amino Acid and Peptide Synthesis, Oxford University Press, Oxford 2002.
- 56 M. Ikeda, in T. Scheper, R. Faurie, J. Thommel (eds.): Advances in Biochemical Engineering/Biotechnology 79 (2003) 1.
- 57 S. Hashimoto, R. Katsumata, L-Alanine production by alanine racemase-deficient mutant of Arthrobacter oxydans in: Proc. Ann. Meet. (Agric. Chem. Soc. Jpn.) (1994) 341.
- 58 S. Yahata, H. Tsutsui, K. Yamada, T. Konehara: “Fermentative production of d-alanine:” in: Proc. Ann. Meet. Agric. Chem. Soc. Jpn., (1993), 92.
- 59 Tanabe Seiyaku, JP-Kokai 58-9692, 1983 (I. Chibata, M. Kisumi, T. Tagaki).
- 60 Ajinomoto, US 5 164 307, 1992 (Y. Yoshihara, Y. Kawahara, Y. Yamada).
- 61 M. Sugiura, S. Suzuki, M. Kisumi, Agric. Biol. Chem. 51 (1987) 371–377.
- 62 Kyowa Hakko, EP-A 557 996, 1993 (K. Kino, K. Okamoto, Y. Takeda, Y. Kuratsu).
- 63 C. Keilhauer, L. Eggeling, H. Sahm, J. Bacteriol. 175 (1993) 5595–5603.
- 64 Cheil Sugar, FR 2 645 172, 1990 (J. W. Oh, S. J. Kim, Y. J. Cho, N. H. Park, L. H. Lee).
- 65 University Odessa, SU 1 730 152, 1992 (I. I. Brown et al.).
- 66 Sci. Res. Technol Inst. Amino Acids, USSR, DE-OS 3 612 077, 1986 (Š. M. Kocarian et al.).
- 67 All Union Sci.-Res. Inst. Genetics and Microorg. Gen. + Selec Univ. Odessa, WO 90/04636, 1990 (V. G. Debabov et al.).
- 68 M. Ikeda, K. Nakanishi, K. Kino, R. Katsumata, Biosci. Biotech. Biochem. 58 (1994) 674–678.
- 69 M. Furui, K. Yamashita, J. Ferment, Technol. 61 (1983) 587–591.
- 70 H. Yoshida: Arginine, Citrulline, and Ornithine, in K. Aida et al. (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 131–143.
- 71 I. Chibata, T. Tosa, T. Sato: Aspartic Acid, in H. W. Blanch, S. Drew, D. I. C. Wang (eds.): Comprehensive Biotechnology, vol. 3 , Pergamon Press, Oxford 1985.
- 72 Y. Yokote et al., J. Solid-Phase Biochem. 3 (1978) 247–261.
- 73 M. Terasawa, H. Yukawa, Y. Takayama, Process Biochem. 20 (1985) 124–128.
- 74 T. Sato et al., Biotechnol. Bioeng. 17 (1975) 1779–1804.
- 75 I. Chibata, T. Tetsuya, T. Sato, Appl. Biochem. Biotechnol. 13 (1986) 231–240.
- 76 M. C. Fusee, W. E. Swann, G. J. Calton, Appl. Environ. Microbiol. 42 (1981) 672–676.
- 77 Genex, EP-A 197 784, 1986 (W. E. Swann, A. C. Nolf).
- 78 J. Michelet, A. Deschamps, J. M. Lebeault, 3rd Eur. Congr. Biotechnol., vol. 2, Verlag Chemie, Weinheim, Germany 1984, pp. 133–138.
- 79 M. Mori, I. Shiio, Agric. Biol. Chem. 48 (1984) 1189–1197.
- 80 N. Nishimura, S. Komatsubara, M. Kisumi, Appl. Environ. Microbiol. 53 (1987) 2800–2803.
- 81 Maggi, DE 2 449 711, 1979 (P. Hirsbrunne, R. Bertholet).
- 82 Mitsubishi Chemical Ind., US 3974031, 1976 (H. Yamada, K. Gumagai, H. Ohkishi).
- 83 Consortium für Elektrochemische Industrie GmbH, WO 01/27307, 2001 (T. Maier, C. Winterhalter).
- 84 T. H. P Maier, Nat. Biotechnol. 21 (2003) 422.
- 85 K. Sano, K. Mitsugi, Agric. Biol. Chem. 42 (1978) 2315–2321.
- 86 S. Kinoshita, S. Ukada, M. Shimono, J. Gen. Appl. Microbiol. 3 (1957) 139–205.
- 87 S. Kinoshita, K. Tanaka: Glutamic acid, in K. Yamada, et al. (eds.): The Microbial Production of Amino Acids, John Wiley & Sons, New York 1972, pp. 263–324.
- 88 L. Eggeling: Handbook of Corynebacterium Glutamicum, CRC Press, Boca Raton, FL 2005.
- 89 B. J. Eikmans, M. Kircher, D. J. Reinscheid, FEMS Microbiol. Lett. 82 (1991) 203–208.
- 90 W. Liebl, M. Ehrmann, W. Ludwig, K. H. Schleifer, Int. J. Syst. Bacteriol. 41 (1991) 225–235.
- 91 Y. Hirose, H. Enei, H. Shibai: L-Glutamic acid fermentation, in H. W. Blanch, S. Drew, D. I. C. Wang (eds.): Comprehensive Biotechnology, vol. 3, Pergamon Press Ltd., Oxford 1985.
- 92 M. Kikuchi, Y. Nakao: Glutamic acid, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 101–116.
- 93 R. Krämer, BioEngineering 9 (1993) 51–61.
- 94 R. Krämer, FEMS Microbiol. Rev. 13 (1994) 75–93.
- 95
I. Shiio,
K. Ujigawa,
Agric. Biol. Chem.
42
(1980)
1897–1904.
10.1271/bbb1961.44.1897 Google Scholar
- 96 E. R. Börmann, B. J. Eikmanns, H. Sahm, Molecular Microbiol. 6 (1992) 317–326.
- 97 T. E. Walker et al., J. Biol. Chem. 257 (1982) 1189–1195.
- 98
H. Yoishii
et al.,
Nippon Nogei Kagaku Kaishi
67
(1993)
949–954.
10.1271/nogeikagaku1924.67.949 Google Scholar
- 99
H. Yoishii,
M. Yoshimura,
S. Nakamori,
S, Inoue,
Nippon Nogei Kagaku Kaishi
67
(1993)
955–960.
10.1271/nogeikagaku1924.67.955 Google Scholar
- 100 Ajinomoto, JP 56 148 295, 1981 (T. Tsuchida, K. Miwa, S. Nakamori, H. Mimose).
- 101
M. Shirasuchi
et al.,
Biosci. Biotechnol. Biochem.
59
(1995)
83–86.
10.1271/bbb.59.83 Google Scholar
- 102 T. Tsuchida et al., Agric. Biol. Chem. 51 (1987) 2089–2094.
- 103 K. Araki: Histidine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 247–256.
- 104 M. B. Vickery, J. Biol. Chem. 143 (1942) 77.
- 105 Kyowa Hakko, EP-A 759 472, 1996 (A. Ozaki, H. Mori, T. Shibasaki).
- 106 J. Ogawa, S. Shimizu, Curr. Opin. Biotechnol. 13 (2002) 367.
- 107 I. Eggeling, C. Cordes, L. Eggeling, H. Sahm, Appl. Microbiol. Biotechnol. 25 (1987) 346–351.
- 108 E. Scheer, L. Eggeling, H. Sahm, Appl. Microbiol. Biotechnol. 28 (1988) 474–477.
- 109 C. Wilhelm et al., Appl. Microbiol. Biotechnol. 31 (1989) 458–462.
- 110 Ajinomoto, Patent 5 164 307, 1992 (Y. Yoshihara, Y. Kawahara, Y. Yamada).
- 111 S. Komatsubara, M. Kisumi, I. Chibata, J. Gen. Microbiol. 119 (1980) 51–61.
- 112 Ajinomoto, EP-A 519 113, 1992 (V. A. Livshits et al.).
- 113 Kyowa Hakko, EP-A 595 163, 1994 (T. Nakano, T. Azuma, Y. Kuratsu).
- 114 Forsch. Z. Jülich, DE 44 00 926, 1995 (B. Möckel, L. Eggeling, H. Sahm).
- 115 Kyowa Hakko, US 5 362 637, 1994 (K. Kino, Y. Kuratsu).
- 116 S. Morbach, H. Sahm, L. Eggeling, Appl. Environ. Microbiol. 61 (1995) 4315–4320.
- 117 Ajinomoto, EP-A 685 555, 1995 (K. Hashiguchi, H. Kishino, N. Tsujimoto, H. Matsui).
- 118 U. Groeger, H. Sahm, Appl. Microbiol. Biotechnol. 25 (1987) 352–236.
- 119 S. Komatsubara, M. Kisumi: Histidine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amio Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 233–246.
- 120 Ajinomoto, US 5 164 307, 1992 (Y. Yoshihara, Y. Kawahara, Y. Yamada).
- 121 M. Karasawa, O. Tosaka, S. Ikeda, H. Yoshi, Agric. Biol. Chem. 50 (1986) 339–346.
- 122 Kyowa Hakko, US 4 623 623, 1986 (T. Nakanashi et al.).
- 123 Kawahara et al., Appl. Microbiol. Biotechnol. 34 (1990) 87–90.
- 124 Ajinomoto, US 5 250 423, 1993 (Y. Murakami, H. Miwa, S. Nakamori).
- 125 A. Erdmann, B. Weil, R. Krämer, Appl. Microbiol. Biotechnol. 42 (1994) 604–610.
- 126 A. Erdmann, B. Weil, R. Krämer, Biotechnol. Lett. 17 (1995) 927–932.
- 127 R. Krämer, J. Biotechnol. 45 (1996) 1–21.
- 128 M. S. N. Jetten, A. J. Sinskey, Crit. Rev. in Biol. 15 (1995) 73–103.
- 129 Kyowa Hakko, EP-A 197 335, 1986 (R. Katsumata, T. Mitzukami, T. Oka).
- 130 Forsch. Z. Jülich, EP-A 435 132, 1991 (J. Cremer, L. Eggeling, H. Sahm).
- 131 Y.-C. Liu, W.-T. Wu, J.-H. Tsao, Bioprocess. Eng. 9 (1993) 135–139.
- 132 Eurolysine, EP-A 534 865, 1993 (P. Lucq, C. Domont).
- 133 Rhone-Polenc, EP 122 163, 1984 (N. Rouy).
- 134 Degussa, EP 533 039, 1993 (W. Binder et al.).
- 135 Degussa, DE 2 421 167, 1974 (T. Lüßling, K. Müller, G. Schreyer, F. Theissen).
- 136 W. Leuchtenberger, U. Plöcker: Amino acids and hydroxycarboxylic acids, in W. Gerhartz (ed.): Enzymes in Industry, Production and Applications, VCH, Weinheim, Germany 1990.
- 137 T. Ishikawa et al., Biosci. Biotech. Biochem. 57 (1993) 982–986.
- 138 Genencor, WO 93/17112, 1993 (J. C. Lievense).
- 139 Genex, US 4 598 047, 1986 (J. C. McGuire).
- 140 C. T. Evans, C. Coma, W. Petreson, M. Misawa, Biotechnol. Bioeng. 30 (1987) 1067–1072.
- 141 G. J. Calton et al., Biotechnology 4 (1986) 317–320.
- 142 C. T. Evans et al., Biotechnology 5 (1987) 818–923.
- 143 A. J. Pittard, Amer. Soc. Microbiol. Conf. Proc. (1987) 368–394.
- 144 I. Shiio: Tryptophan, phenylalanine, and tyrosine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 188–206.
- 145 S. O. Hwang et al., Appl. Microbiol. Biotechnol. 22 (1985) 108–113.
- 146 H. Ito et al., Agric. Biol. Chem. 54 (1990) 707–713.
- 147 B. K. Konstantinov, N. Nishio, T. Yoshida: “Glucose feeding strategy accounting for the decreasing oxidative capacity of recombinant Escherichia coli in fed-batch cultivation for phenylalanine production,” J. Ferment. Bioeng. 70 (1990) 253.
- 148 Ajinomoto, US 4 584 400, 1986 (M. Ootani, S. Sano, I. Kusumotu).
- 149 A. M. Vasconcellos, A. L. Neto, D. M. Grassiano, C. P. De Oliveira, Biotechnol. Bioeng. 33 (1989) 1324–1329.
- 150 Ajinomoto, US 5 362 635, 1994 (T. Hirose et al.).
- 151 F. Yoshinaga: Proline, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 117–120.
- 152 M. Sugiura, T. Takagi, M. Kisumi, Abst. 31st Symp. Amino Acid and Nucleic Acid (Japan), 1982, p. 10.
- 153 Y. Imai, T. Takagi, M. Sugiura, M. Kisumi, Abst. Ann. Meet Agr. Chem. Soc. (Japan), 1984, p. 100.
- 154 Y. Izumi et al., Appl. Microbiol. Biotechnol. 39 (1993) 427–432.
- 155 T. Yoshida, T. Mitsunaga, Y. Izumi, J. Fermentation Bioeng. 75 (1993) 405–408.
- 156 H.-Y. Hsiao, T. Wie, Biotechnol. Bioeng. 28 (1986) 1510–1518.
- 157 Mitsui Toatsu, US 5 382 517, 1995 (D. Ura, T. Hashimukai, T. Matsumoto, N. Fukuhara).
- 158 K. Shimura: Threonine, in H. W. Blanch, S. Drew, D. I. C. Wang (eds.): Comprehensive Biotechnology, vol. 3, Pergamon Press, Oxford 1985.
- 159 S. Nakamori: Threonine and Homoserine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Progress in Industrial Microbiology, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 173–182.
- 160 Genetics Ind., US 4 278 765, 1981 (V. G. Debabov et al.).
- 161 Ajinomoto, EP-A 593 792, 1994 (V. G. Debabov et al.).
- 162 Eurolysine, FR 2 627 508, 1989 (F. Richaud et al.).
- 163 Ajinomoto, FR 2 588 016, 1987 (M. Ootani, T. Kitahara, K. Akashi).
- 164 A. Yokota, T. Takao, Agric. Biol. Chem. 48 (1984) 2663–2668.
- 165 Mitsui Toatsu, EP-A 341 674, 1989 (K. Ishiwata et al.).
- 166 Mitsui Toatsu, EP-A 438 591, 1991 (S. Ogawa, S. Iguichi, S. Morita, H. Kuwamoto).
- 167 B. K. Hamilton et al., Trends Biotechnol. 3 (1985) 64–68.
- 168 J. Plachy, S. Ulbert, Acta Biotechnol. 10 (1990) 517–522.
- 169 Showa Denko, JP 62 186 786, 1987 (E. Takinishi, H. Takamatsu, K. Sakimoto, Y. Yajima).
- 170 A. N. Mayeno, G. J. Gleich, TIBTECH 12 (1994) 346–352.
- 171 K. Sakimoto, Y. Torigoe, Curr. Prospects Med. Drug Saf. (1994) 295–311.
- 172 K. Nakayama: Tryptophan, in M. Moo-Young (ed.): Comprehensive Biotechnology, vol. 3, Pergamon Press, Oxford 1985, 621–631.
- 173 I. Shiio: Tryptophan, Phenylalanine, and Tyrosine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds.): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 188–206.
- 174 T. K. Maiti, S. P. Chatterje, Hindustan Antibiotics Bulletin 33 (1991) 26–61.
- 175 M. Ikeda, Appl. Microbiol. Biotech. 69 (2006) 615.
- 176 S. Komatsubara, M. Kisumi: Isoleucine, Valine, and Leucine, in K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada (eds): Biotechnology of Amino Acid Production, Kodansha, Tokyo/Elsevier, Amsterdam 1986, pp. 131–143.
- 177 Ajinomoto, EP 287 123, 1993 (N. Katsurada, H. Uchibori, T. Tsuchida).
- 178 D. A. Bender: Amino Acid Metabolism, J. Wiley & Sons, London–New York–Sydney–Toronto 1975, p. 2.
- 179 H. N. Munro, Drug Intell. Clin. Pharm. 6 (1972) 216.
- 180 M. L. Sunde, Poult. Sci. 51 (1972) 44.
- 181 R. F. Barker, D. A. Hopkinson, Ann. Hum. Genet. 41 (1977) 27.
- 182 L. D. Stegink: Clinical Nutrition Update: Amino Acids, Am. Med. Assoc. Publ., Chicago 1977, pp. 198–205.
- 183 K. Schreier, Ärztl. Fortbildung 19 (1971) 107.
- 184 U. Porath, K. Schreier, Med. Ernähr. 11 (1970) 229.
- 185 H. Bickel, S. Kaiser-Grubel, Dtsch. Med. Wochenschr. 96 (1971) 1415.
- 186 Y. Izumi, I. Chibata, T. Itoh, Angew. Chem. 90 (1978) 187; Angew. Chem. Int. Ed. Eng. 17 (1978) 176.
- 187
M. S. Sadovnikova,
V. M. Belikov,
Russ. Chem. Rev. (Engl. Transl.)
47
(1978)
199.
10.1070/RC1978v047n02ABEH002212 Google Scholar
- 188 K. Drauz, A. Kleemann, J. Martens, Angew. Chem. 94 (1982) 590; Angew. Chem. Int. Ed. Engl. 21 (1982) 584.
- 189 Winnacker-Küchler, 5th ed., vol. 8, 715.
- 190 FAO: Nutritional Studies No. 24, Amino Acid Content of Foods and Biological Data on Proteins, Interprint (Malta), Rome 1970.
- 191 Degussa, unpublished
- 192 W. C. Rose, Nutr. Abstr. Rev. 27 (1957) 631.
- 193 D. M. Hegsted, Fed. Proc. Fed. Am. Soc. Exp. Biol. 22 (1963) 1424.
- 194 Report of a Joint FAO/WHO Ad Hoc Expert Committee: Energy and Protein Requirements, Rome 1973.
- 195 E. Kofrányi, Ernähr. Umsch. 23 (1976) 205.
- 196 Dtsch. Ges. für Ernährung: Empfehlungen für die Nährstoffzufuhr, 3rd ed., Umschau-Verlag, Frankfurt 1975.
- 197 Dtsch. Ges. Für Ernährung: Referenzwerte für die Nährstoffzufuhr, Umschau Buchverlag, Frankfurt 2000.
- 198 Recommended Dietary Allowances, 9th ed., Nat. Acad. of Sci., Washington, D.C., 1980.
- 199 J. J. Otten, J. P. Hellwig, L. D. Meyers (eds.): Dietary Reference Intakes: the Essential Guide to Nutrient Requirements, National Academies Press, Washington DC 2006.
- 200 G. K. Parman, J. Agric. Food Chem. 16 (1968) 169.
- 201 H. H. Ottenheym, P. J. Jenneskens, J. Agric. Food Chem. 18 (1970) 1010.
- 202 N. S. Scrimshaw, A. M. Altschul: Amino Acid Fortification of Protein Foods, MIT Press, Cambridge, MA 1971.
- 203 E. E. Howe, G. R. Jansen, E. W. Gilfilian, Am. J. Clin. Nutr. 16 (1965) 315.
- 204 A. M. Altschul, Nature (London) 248 (1974) 643.
- 205 J. Kato, N. Muramatsu, J. Am. Oil Chem. Soc. 48 (1971) 415.
- 206 J. Mauron, Z. Ernährungswiss. Suppl. 23 (1979) 10.
- 207 D. M. Hegsted, Am. J. Clin. Nutr. 21 (1968) 688.
- 208 L. D. Satterlee, H. F. Marshall, J. M. Tennyson, J. Am. Oil Chem. Soc. 56 (1979) 103.
- 209 H. W. Staub, Food Technol. (Chicago) 32 (1978) 57.
- 210 F. Jekat, Fette Seifen Anstrichm. 79 (1977) 273.
- 211 J. C. Somogyi in: Die Bedeutung der Eiweiße in unserer Ernährung, Issue 48 a, Schriftenreihe der Schweizer Vereinigung für Ernährung, 1982, p. 3.
- 212 G. G. Graham et al., Am. J. Clin. Nutr. 22 (1969) 1459.
- 213 G. R. Jansen, C. F. Hutchison, M. E. Zanetti, Food Technol. (Chicago) 20 (1966) 323.
- 214 R. Bressani et al., J. Nutr. 79 (1963) 333.
- 215 J. L. Iwan, Cereal Sci. Today 13 (1968) 202.
- 216 D. Rosenfield, F. J. Stare, Mod. Gov. 11 (1970) 47.
- 217 S. N. Gershoff et al., Am. J. Clin. Nutr. 30 (1977) 1185.
- 218 H. N. Parthasarathy et al., Can. J. Biochem. 42 (1964) 385.
- 219 S. J. Fomon et al., Am. J. Clin. Nutr. 32 (1979) 2460.
- 220 A. L. Jung, S. L. Carr, Clin. Pediatr. (Philadelphia) 16 (1977) 982.
- 221 Procter & Gamble, US 3878305, 1975 (R. A. Damico, R. W. Boggs).
- 222 S. Wallrauch, Flüss. Obst 44 (1977) 386.
- 223 H. D. Pruss, I. P. G. Wirotama, K. H. Ney, Fette Seifen Anstrichm. 77 (1975) 153.
- 224 C. Ambrosino et al., Minerva Pediatr. 18 (1966) 759.
- 225 C. A. Masschelein, J. Van de Meerssche, Tech. Q. Master Brew. Assoc. Am. 13 (1976) 240.
- 226 T. Take, H. Otsuka, Chem. Abstr. 70 (1969) 46270 m.
- 227 J. Koch, Flüss. Obst 46 (1979) 212.
- 228 G. Baumann, K. Gierschner, Dtsch. Lebensm. Rundsch. 70 (1974) 273.
- 229 A. Askar, H. J. Bielig, Alimenta 15 (1976) 3.
- 230 W. Hashida, Food Trade Rev. 44 (1974) 21.
- 231 Food Technol. (Chicago) 34 (1980) 49.
- 232 B. Lindemann, Nat. Neurosci. 3 (2000) 99.
- 233 S. Schwimmer, D. G. Guadagni, J. Food Sci. 32 (1967) 405.
- 234 Riken Kagaku, JP 7249707, 1972 (H. Watanabe et al.); Chem. Abstr. 79 (1973) 114219 q.
- 235 Pillsbury Comp., US 3510310, 1970.
- 236 C. Colburn, Am. Soft Drink J. 126 (1971) 16.
- 237 R. S. Shallenberger, T. E. Acree, C. Y. Lee, Nature (London) 221 (1969) 556.
- 238 J. Solms, L. Vuataz, R. H. Egli, Experientia 21 (1965) 693.
- 239 H. Wieser, H. Jugel, H.-D. Belitz, Z. Lebensm. Unters. Forsch. 164 (1977) 277.
- 240 R. H. Mazur, J. M. Schlatter, A. H. Goldkamp, J. Am. Chem. Soc. 91 (1969) 2684
- 241
L. A. Pavlova
et al.,
Russ. Chem. Rev. (Engl. Transl.)
50
(1981)
316.
10.1070/RC1981v050n04ABEH002602 Google Scholar
- 242 W. J. Herz, R. S. Shallenberger, Food Res. 25 (1960) 491.
- 243 Lever Brothers, US 3922365, 1975 (K. H. Ney et al.).
- 244 H. Tanaka, Y. Obata, Agric. Biol. Chem. 33 (1969) 147.
- 245 M. Giaccio, L. Surricchio, Quad. Merceol. 16 (1977) 151.
- 246 H. Valaize, G. Dupont, Ind. Agric. Aliment. 68 (1951) 245.
- 247 E. L. Wick, M. DeFigueiredo, D. H. Wallace, Cereal Chem. 41 (1964) 300.
- 248 A. A. M. El-Dash, Dissertation, Kansas State University 1969 (Univ. Microfilms Inc., Ann Arbor, Michigan, No. 69-21123).
- 249 W. Baltes, Ernähr. Umsch. 20 (1973) 35.
- 250 M. Angrick, D. Rewicki, Chem. Unserer Zeit 14 (1980) 149.
- 251 H. E. Nurstein, Food Chem. 6 (1980) 263.
- 252 T. A. Rohan, Food Technol. (Chicago) 24 (1970) 29.
- 253
Maggi,
DE 2246032,
1973
(R. J. Gasser).
Z. Mielniczuk
et al.,
Acta Aliment. Pol.
2
(1976)
213.
Chas. Pfizer & Co.,
US 3365306,
1968
(M. A. Perret).
Y.-P. C. Hsieh
et al.,
J. Sci. Food Agric.
31
(1980)
943.
R. A. Wilson,
J. Agric. Food Chem.
23
(1975)
1032.
P. van de Rovaart,
J.-J. Wuhrmann,
US 3930044,
1975.
R. Schroetter,
G. Woelm,
Nahrung
24
(1980)
175.
10.1002/food.19800240208 Google Scholar
- 254 H. Kisaki, Chem. Abstr. 69 (1968) 9824 d. Ajinomoto, FR 2005896 (1969). G. Rubenthaler, Y. Pomeranz, K. F. Kinney, Cereal Chem. 40 (1963) 658. I. R. Hunter, M. K. Mayo, US 3425840, 1969. Y. H. Liau, C. C. Lee, Cereal Chem. 47 (1970) 404. Y.-Y. Linko, J. A. Johnson, B. S. Miller, Cereal Chem. 39 (1962) 468. G. L. Bertram, Cereal Chem. 30 (1953) 126. Research Corp., US 3268555, 1966 (L. Wiseblatt). Hoffmann-La Roche, US 3547659, 1970 (W. Cort, L. Neck). M. Rothe, Nahrung 24 (1980) 185. A. A. El-Dash, A. A. Johnson, Cereal Chem. 47 (1970) 247. L. Wiseblatt, H. F. Zoumut, Cereal Chem. 40 (1963) 162. M. Rothe, Ernährungsforschung 5 (1960) 131.
- 255 G. Ziegleder, D. Sandmeier, Dtsch. Lebensm. Rundsch. 78 (1982) 315. W. Mohr, E. Landschreiber, Th. Severin, Fette Seifen Anstrichm. 78 (1976) 88. S. Turos, US 4346121, 1982.
- 256 E. Cremer, M. Riedmann, Monatsh. Chem. 96 (1965) 364.
- 257 Yuki Gosei Kogyo, US 3478015, 1969 (I. Onishi, A. Nishi, T. Kakizawa).
- 258 Fuji Oil Co., GB 1357511, 1974; GB 1488282, 1977.
- 259 Naarden Int., NL 7712745, 1979.
- 260 J. A. Newell, M. E. Mason, R. S. Matlock, J. Agric. Food Chem. 15 (1967) 767.
- 261 S.-C. Lee, B. R. Reddy, S. S. Chang, J. Food Sci. 38 (1974) 788. Research Corp., US 3814818, 1974 (S. S. Chang, B. R. Reddy). T. Y. Fan, M. H. Yueh, J. Food Sci. 45 (1980) 748. P. T. Arroyo, D. A. Lillard, J. Food Sci. 35 (1970) 769.
- 262 Yuki Gosei Kogyo, DE 1593733, 1972 (I. Onishi et al.). Japan Monopoly, Tanabe Seiyaku, US 3722516, 1973 (K. Suwa et al.). Philip Morris, US 4306577, 1981 (D. L. S. Wu, J. W. Swain). Reynolds Tobacco, US 3996941, 1976 (C. W. Miller, J. P. Dickerson, C. E. Rix).
- 263 R. G. Henika, N. E. Rodgers, Cereal Chem. 42 (1965) 397.
- 264 J. M Bruemmer, W. Seibel, H. Stephan, Getreide Mehl Brot 34 (1980) 173. Patent Technology, US 3803326, 1974. J. Geittner, Gordian 79 (1979) 202.
- 265 R. Marcuse, Fette Seifen Anstrichm. 63 (1961) 940.
- 266 H. Iwainsky, C. Franzke, Dtsch. Lebensm. Rundsch. 52 (1956) 129. H. Lingnert, C. E. Eriksson, J. Food Process. Preserv. 4 (1980) 161.
- 267 N. Watanabe et al., JP 7314042, 1973; Chem. Abstr. 79 (1973) 145052 j.
- 268 A. G. Castellani, Appl. Microbiol. 1 (1953) 195. Nisshin Flour Milling, JP 7319945, 1973(G. Ogawa, K. Taguchi); Chem. Abstr. 81 (1974) 76689 z. Nippon Kayaku, JP-Kokai 81109580, 1981; Chem. Abstr. 95 (1981) 202313 b.
- 269 US Functional Beverages Market, Frost & Sullivan, London, 2004.
- 270 Ajinomoto Co. Inc.: Amino Acid Link News, No. 14 (May 2006). Available at http://www.ajinomoto.com/aminoacid/link/E/pdf/Vol.14E.pdf.
- 271 M. Pack: Amino Acids in Animal Nutrition, Coral Sanivet, Bucharest 2002.
- 272 M. Kirchgeßner: Tierernährung, 11th ed., DLG-Verlag, Frankfurt 2004.
- 273 Nutrient Requirements of Poultry, 9th revised ed., National Academies Press, Washington DC 1994.
- 274 Nutrient Requirements of Swine, 10th revised ed., National Academies Press, Washington DC 1998. P. L. M. Berende, H.-L. Bertram, Z. Tierphysiol. Tierernähr. Futtermittelk. 49 (1983) 30. H.-L. Bertram, P. L. M. Berende, Kraftfutter (1983) 46.
- 275 Degussa Feed Additives: available at http://www.aminoacidsandmore.com.
- 276 M. L. Scott, M. C. Nesheim, R. J. Young: Nutrition of the Chicken, 3rd ed., M. L. Scott, Ithaka, New York, 1982.
- 277 W. Prinz, A. Becker, Arch. Geflügelk. 29 (1965) no. 2, 135.
- 278 R. Chernoff, J. Am. Diet. Assoc. 79 (1981) 426. M. R. Polk, Am. Pharm. NS 22 (1982) 25.
- 279 W. F. Caspary, Dtsch. Ärztebl. 1978 (2. Febr.) 243. H. Kasper, Aktuel. Ernährung 1 (1978) 22.
- 280 D. M. Matthews, S. A. Adibi, Gastroenterology 71 (1976) 151. M. T. Lis, R. F. Crampton, D. M. Matthews, Br. J. Nutr. 27 (1972) 159.
- 281 Mead Johnson, US 3091569, 1963; US 3184505, 1965.
- 282 H. A. Smith, G. Gorin, J. Org. Chem. 26 (1961) 820.
- 283 A. Kleemann, J. Engel: Pharmaceutical Substances, 4th ed., Thieme Verlag, Stuttgart 2001.
- 284 Rech. et Propagande Scientif., FR 1288907, 1962.
- 285 Degussa, US 4129593, 1978.
- 286 Drugs of the Future 23 (1998) 374.
- 287 M. Bergmann, G. Michalis, Ber. Dtsch. Chem. Ges. 63 (1930) 987.
- 288 Degussa, DE 1239697, 1963.
- 289 May & Baker, GB 845 034, 1957.
- 290 B. Witkop et al., J. Am. Chem. Soc. 76 (1954) 5579.
- 291 A. J. Morris et al., J. Org. Chem. 22 (1957) 306.
- 292 E. A. Bell et al., Nature (London) 210 (1966) 529.
- 293 Distillers, GB 854339, 1957. Squibb, US 3281461, 1966. Heyl & Co., DE 2114329, 1971; DE 2413185, 1974.
- 294 Degussa, DE 1795299, 1968; DE 1795297, 1968; DE 2032952, 1970; DE 2123232, 1971; DE 2156601, 1971; DE 2335990, 1973; DE 2138122, 1971; DE 2258411, 1972; DE 2304055, 1973.
- 295 K. Schrader, Am. Cosmet. Perfum. 87 (1972) 49. S. Tatsumi, Am. Cosmet. Perfum. 87 (1972) 61. O. K. Jacobi, Am. Cosmet. Perfum. 87 (1972) 35. G. Hopf, J. König, G. Padberg, Kosmetologie 4 (1971) 132. A. Szakall, Arch. Klin. Exp. Dermatol. 201 (1955) 331. K. Laden, R. Spitzer, J. Soc. Cosmet. Chem. 18 (1967) 351. H. W. Spier, G. Pascher, Klin. Wochenschr. 31 (1953) 997.
- 296 Y. Kumano et al., J. Soc. Cosmet. Chem. 28 (1977) 285.
- 297 L'Oreál, DE 2807607, 1978 (J.-C. Ser et al.). Unilever, DE 2337342, 1973 (G. F. Johnston et al.). Orlane Paris, DE 2524297, 1975 (A. Meybeck, H. Noel). Shiseido, US 4035513, 1977 (Y. Kumano).
- 298 E. S. Cooperman, Am. Cosmet. Perfum. 87 (1972) 65. Colgate Palmolive, GB 1573529, 1980.
- 299 Proctor and Gamble: Press Release, 23 August 2004; available at http://www.uk.pg.com.
- 300
C. R. Robbins:
Chemical and Physical Behaviour of Human Hair,
Springer Verlag,
Berlin
1994.
10.1007/978-1-4757-3898-8 Google Scholar
- 301 European Markets for Active Ingredients in Personal Care, Frost & Sullivan, London, 2004.
- 302 M. Takehara et al., J. Am. Oil Chem. Soc. 50 (1973) 227; 51 (1974) 419.
- 303 Ajinomoto, Kawaken Fine Chemicals, US 4273684, 1981 (T. Nagashima et al.)
- 304 Ajinomoto, GB 1483500, 1977.
- 305 Kawaken Fine Chemicals. JP-Kokai 75117806, 1975 (K. Nakazawa); Chem. Abstr. 84 (1976) 8858 r.
- 306 G. Schuster, H. Modde, E. Scheld, Seifen Öle Fette Wachse 38 (1965) 477. G. Schuster, H. Modde, Parfüm + Kosmet. 45 (1964) 337.
- 307 Estee Lauder, US 4005210, 1977 (J. Gubernick).
- 308 American Cyanamid, US 3988438, 1976. Ajinomoto, DE 2010303, 1970 (R. Yoshida et al.).
- 309 R. Yoshida, M. Takehara, Chem. Abstr. 84 (1976) 6843 h.
- 310 M. Koyama, J. Dispersion Sci. Tech. 26 (2005) 785.
- 311 Dominion Pharmacal., US 4176197, 1979 (B. N. Olson). L'Oréal, US 4002634, 1977 (G. Kalopissis, C. Bouillon). L'Oréal, GB 1397623, 1975 (G. Kalopissis, G. Manoussos). L'Oréal, DE 1492071, 1965 (G. Kalopissis).
- 312 Mare Corp., US 4201235, 1980 (V. G. Ciavatta). Unilever, EP 8171, 1981 (G. P. Mathur et al.).
- 313 Kyowa Hakko Kogyo, US 4139610, 1979 (Y. Miyazaki et al.) Hans Schwarzkopf, DE 958501, 1957 (J. Saphir, E. Kramer). K. Yoneda et al., DE 2951923, 1979.
- 314 Schuylkill Chem., GB 1516890, 1978.
- 315 Procter & Gamble, EP 47650, 1982. Unilever, GB 1597498, 1981 (K. Gosling, M. R. Hyde).
- 316 Sederma, US 6974799, 2003 (K. Lintner).
- 317 Sederma, WO 98/07744, 1998 (D. Greff).
- 318 C. Tomlin (ed.): The Pesticide Manual, 13th ed., British Crop Protection Council, Farnham 2003.
- 319 B. Hock, C. Fedtke, R. R. Schmidt: Herbizide, 1st ed., Georg Thieme Verlag Stuttgart 1995.
- 320 Proc. North. Cent. Weed Control Conf. 26 (1971) 64.
- 321 P. Knuuttila, H. Knuuttila, Acta Chem. Scand. 33 (1979) 623.
- 322 Agrochemical Service, Wood Mackenzie Consultants Limited, Edinburgh 1996.
- 323 Zeneca, US 4 315 765.
- 324 Z. Pflanzenkr. Pflanzenschutz (1981) Sonderheft IX, 431.
- 325 Hoechst, DE-OS 2 717 440, 1976.
- 326 K. Tachibana et al., Abstr. 5th Int. Congr. Pestic. Chem., IVa Abstract 19.
- 327 D. W. Ladner, Pestic. Sci. 29 (1990) 341–356.
- 328 M. J. Muhitch, D. L. Shaner, M. A. Stidham, Plant Physiol. 83 (1987) 451–456.
- 329 T. Chapman et al., Symp. New. Herbic. 3rd ed. (1969) 40.
- 330 R. M. Scott et al., Proc. Br. Crop. Prot. Conf.–Weeds 2 (1976) 723.
- 331 S. O. Duke et al., Pestic. Sci. 40 (1994) 265–277.
- 332 N. Mito, R. Sato, M. Miyakado, H. Oshio, S. Tanaka, Pestic. Biochem. Physiol. 40 (1991) 128–135.
- 333 Degussa, WO 94/03458, 1994 (M. Schäfer, H. Baier, K. Drauz, H.-P. Krimmer, S. Landmann).
- 334 Sumitomo, JP 62 158 280.
- 335 BASF, DE 409 432, 1994.
- 336 BASF, DE 407 023, 1994.
- 337 American Cyanamid Co., EP 101 098, 1993.
- 338 Bayer, DE 030 062, 1990.
- 339 S. Sauza et al., Phytoma–la défense des vegetaux 558 (2003) 51.
- 340 Y. Miyake et al., Nippon Noyaku Gakkaishi 30 (2005) 390.
- 341 P. A. Urech, Proc. Br. Crop. Prot. Conf.–Pests Dis. 2 (1977) 623.
- 342 Garavaglia et al.: Atti Simp. Chim. Antiparassitari, 3rd, Piacenza 1981.
- 343 C. A. Henrick et al., Pestic. Sci. 11 (1980) 224.
- 344 C. A. Porter, L. E. Ahlrichs, Hawaii Sugar Tech. Rep. 1971 30 (1972) 71.
- 345 Ciba Geigy, EP 18948, 1980.
- 346 Emori Shoji, JP 78097022, 1978.
- 347 Dainichi Seika Kogy, JP 78079990, 1978.
- 348 L. Mueller, Zem. Kalk Gips 27 (1974) 69.
- 349 Ajinomoto, DE 2533136, 1975 (R. Yoshida et al.).
- 350 Kyowa Fermentation, GB 1400741, 1975. Honny Chemicals, GB 1402758, 1975 (Y. Nakagoshi). Kyowa Hakko Kogyo, DE 2229488, 1972 (Y. Fujimoto et al.). Toyo Cloth, US 3676206, 1972 (K. Nishitani et al.).
- 351 Sanyo Trading Co., DE 2716758, 1977 (M. Onizawa, S. Ohmiya).
- 352 Ajinomoto, JP 81035179, 1981. Ajinomoto, JP-Kokai 7522801, 1975 (T. Saito et al.); Chem. Abstr. 84 (1976) 33494 b.
- 353 Sanyo Trading Co., DE 2602988, 1976; US 4069213, 1978; DE 2604053, 1976 (M. Onizawa); DE 2658693, 1976 (M. Onizawa, S. Ohmiya).
- 354 R. M. Saleh, A. M. Shams El Din, Corros. Sci. 12 (1972) 688.
- 355 Ajinomoto, JP-Kokai 7426145, 1974 (Y. Kita et al.); Chem. Abstr. 81 (1974) 53195 w.
- 356 Ilford, GB 1378354, 1974 (A. D. Ezekiel). Ilford, DE 2316632, 1973 (R. Jefferson).
- 357 Fr. Blasberg & Co., DE 2050870, 1973 (W. Immel, W. Adams). Yokozawa Chemical Ind., JP 7410572, 1974 (K. Aoya et al.); Chem. Abstr. 81 (1974) 57631 h. Sony Corp., DE 2325109, 1973 (S. Fueki et al.).
- 358 A. Steponavicius, R. Visomirskis, Electrodepos. Surface Treat. Lausanne 1 (1972) 37.
- 359 F. S. Parker, D. M. Kirschenbaum, Spectrochim. Acta 16 (1960) 910. M. Tsuboi, T. Takenishi, A. Nakamura, Spectrochim. Acta 19 (1963) 271. J. F. Pearson, M. A. Slifkin, Spectrochim. Acta Part A 28 (1972) 2403.
- 360 C. S. Tsai et al., Can. J. Biochem. 53 (1975) no. 9, 1005.
- 361 H. Hagenmeyer et al., Z. Naturforsch. B: Anorg. Chem. Org. Chem. 25 B (1970), 681.
- 362 C. Cooper, W. Packer, K. Williams: Amino Acid Analysis Protocols, Methods in Molecular Biology Series, 159, Humana Press, Totowa, NJ 2000.
- 363 W. S. Hancock: Handbook for the Separation of Amino Acids, Peptides and Proteins, vol. 1, CRC Press, Boca Raton, FL, 1984.
- 364 E. Scoffone, A. Fontana, Mol. Biol. Biochem. Biophys. 8 (1970) 185.
- 365 M. Roth, Anal. Chem. 43 (1971) 880. J. R. Benson, P. E. Hare, Proc. Natl. Acad. Sci. USA 72 (1975) 619.
- 366 E. Bayer et al., Anal. Chem. 48 (1976) 1106.
- 367 S. Udenfried et al., Science (Washington, D.C.) 178 (1972) 871.
- 368 I. Molnár-Perl: Quantitation of Amino Acids and Amines by Chromatography, Elsevier, Oxford, 2005.
- 369 C. Haworth, R. W. A. Oliver, J. Chromatogr. 64 (1972) 305. E. Stahl: Dünnschichtchromatographie, Springer Verlag, Berlin 1967, p. 701. A. R. Fahmy et al., Helv. Chim. Acta 44 (1959) 245.
- 370 M. Kubota et al., Anal. Biochem. 64 (1975) no. 2, 494. K. D. Kulbe, Anal. Biochem. 44 (1970) 548. P. A. Laursen, Biochem. Biophys. Res. Commun. 37 (1969) 663.
- 371 A. Wolf, Prax. Naturwiss. Chem. 23 (1974) no. 3, 74.
- 372 H. Nakamura, J. J. Pisano, J. Chromatogr. 121 (1976) 33.
- 373 K. Macek, Z. Deyl, M. Smrž, J. Chromatogr. 193 (1980) 421.
- 374 P. B. Hamilton, Anal. Chem. 35 (1963) 2055.
- 375 S. Blackburn: Amino Acid Determination, Marcel Dekker, New York 1978.
- 376 D. H. Spackman, W. H. Stein, S. Moore, Anal. Chem. 30 (1958) 1190.
- 377 S. Moore, W. H. Stein, J. Biol. Chem. 211 (1954) 907.
- 378 H.-M. Lee et al., Anal. Biochem. 96 (1979) 298.
- 379 P. Chaimbault et al., J. Chromatogr. A, 870 (2000) 245.
- 380 J. Weiss: Handbook of Ion Chromatography, Wiley-VCH, Weinheim 2004.
- 381 E. Bayer et al., Anal. Chem. 48 (1976) 1106. J. M. Wilkinson, J. Chromatogr. Sci. 16 (1978) 547. K.-T. Hsu, B. L. Currie, J. Chromatogr. 166 (1978) 555. T. Jamabe, N. Takei, H. Nakamura, J. Chromatogr. 104 (1975) 359. A. Khayat, P. K. Redenz, L. A. Gorman, Food Technol. (Chicago) 36 (1982) 46.
- 382 A. P. Graffeo, A. Haag, B. L. Karger, Anal. Lett. 6 (1973) no. 6, 505. J. K. De Vries, R. Frank, C. Birr, FEBS Lett. 55 (1975) no. 1, 65. P. Frankhauser et al., Helv. Chim. Acta 57 (1974) 271. C. C. Zimmermann, E. Appella, J. J. Pisano, Anal. Biochem. 77 (1977) 569. G. Frank, W. Strubert, Chromatographia 6 (1973) no. 12, 522.
- 383 H. Beyer, U. Schenk, J. Chromatogr. 89 (1969) 483.
- 384 T. A. Kan, W. F. Shipe, J. Food Sci. 47 (1981) 338. H. Umagat, P. Kucera, L. F. Wen, J. Chromatogr. 239 (1982) 463.
- 385 W. Voelter, K. Zech, J. Chromatogr. 112 (1975) 643.
- 386 R. Schuster, Anal. Chem. 52 (1980) 617.
- 387 A. Darbre, Biochem. Soc. Trans. 2 (1974) 70. B. M. Nair, J. Agric. Food Chem. 25 (1977) 614.
- 388 J. J. Pisano, T. J. Bronzert, H. B. Brewer, Anal. Biochem. 45 (1972) 43.
- 389 A. Darbre, A. Islam, Biochem. J. 106 (1968) 923.
- 390 C. W. Gehrke, R. W. Zumwalt, K. Kuo, J. Agric. Food Chem. 19 (1971) 605.
- 391 K. Ruhlmann, W. Giesecke, Angew. Chem. 73 (1961) 113.
- 392 D. L. Stalling, C. W. Gehrke, R. W. Zumwalt, Biochem. Biophys. Res. Commun. 31 (1968) 4.
- 393 M. W. Duncan, A. Poljak, Anal. Chem. 70 (1998) 890.
- 394 W. Grassmann, K. Hannig, Houben-Weyl, 1/1, 708.
- 395 V Poinsot et al., Electrophoresis 27 (2006) 176.
- 396 T. Soga, D. N. Heiger, Anal. Chem. 72 (2000) 1236.
- 397 I. Abe, S. Musha, J. Chromatogr. 200 (1980) 195. G. J. Nicholson, H. Frank, E. Bayer, HRC CC J. High Resolut. Chromatogr. Chromatogr. Commun. 2 (1979) 411. W. A. König, G. J. Nicholson, Anal. Chem. 47 (1975) 951.
- 398 W. Lindner, Chimia 35 (1981) 294. V. A. Davankov et al., Chromatographia 13 (1980) no. 11, 677.
- 399 P. E. Hare, E. Gil-Av, Science (Washington, D.C.) 204 (1979) 1226.
- 400 C. B'Hymer, M. Montes-Bayon, J. A. Caruso, J. Sep. Sci. 26 (2003) 7.
- 401 R. Bhushan, H. Bruckner, Amino Acids 27 (2004) 231.
- 402 L. M. Henderson, E. E. Snell, J. Biol. Chem. 172 (1947) 15. I. Grote, Mühle Mischfuttertech. 116 (1979) 465.
- 403 H. Itoh, T. Morimoto, I. Chibata, Anal. Biochem. 60 (1974) 573.
- 404 Ch. Calvot et al., FEBS Lett. 59 (1975) no. 2, 258. S. J. Updike, G. P. Hicks, Nature (London) 214 (1967) 986.
- 405 Ajinomoto, FR 2421380, 1979.
- 406 European Pharmacopoeia, 5th ed., European Directorate for the Quality of Medicine, Strasbourg 2005.
- 407 W. Seaman, E. Allen, Anal. Chem. 23 (1951) no. 4, 592. H. P. Deppeler, G. Witthans, Fresenius Z. Anal. Chem. 305 (1981) 273.
- 408 United States Pharmacopeia, 29th ed., US Pharmcopeial Convention, Inc., Rockville, MD 2006.
- 409 Food Chemicals Codex, 5th ed., National Academies Press, Washington, D.C. 2003.
- 410 Ajinomoto: Amino Acids Business, 2005 (available at http://www.ajinomoto.com).
- 411 E. O. Camara Greiner, R. Gubler, K. Yokose: Market Research Report: Amino Acids, SRI International, Menlo Park, CA, 2003.
- 412 European Amino Acids Market, Frost & Sullivan, London, 2006.
- 413 K. Brown: Amino Acids: Highlighting Synthesis Applications, Business Communications Co. Inc., Norwalk, CT 2005.
- 414 H. N. Munro, Adv. Exp. Med. Biol. 105 (1978) 119.
- 415 A. E. Harper, N. J. Benevenga, R. M. Wohlhueter, Physiol. Rev. 50 (1970) 428.
- 416 R. G. Daniel, H. A. Waisman, Growth 32 (1968) 255.
- 417 H. E. Sauberlich, J. Nutr. 75 (1961) 61.
- 418 K. Lang: Biochemie der Ernährung, 4th ed., Steinkopff, Darmstadt 1979.
- 419 Y. Peng et al., J. Nutr. 103 (1973) 608.
- 420 Degussa, unpublished, 1973 and 1983. R. J. Breglia, C. O. Ward, C. I. Jarowski, J. Pharm. Sci. 62 (1973) 49. P. Gullino et al., Arch. Biochem. Biophys. 58 (1955) 253. O. Strubelt, C.-P. Siegers, A. Schütt, Arch. Toxicol. 33 (1974) 55. W. Braun, Strahlentherapie 108 (1959) 262. H. Gutbrod et al., Acta Hepatol. 5 (1957) no. 1/2, 1. I. Petersone et al., Eksp. Klin. Farmakoter. 3 (1972) 5. D. G. Gallo, A. L. Sheffner, DE 2018599, 1971. Transbronchin, Homburg Pharma, Frankfurt 1971. L. Bonanomi, A. Gazzaniga, Therapiewoche 30 (1980) 1926. W. F. Riker, H. Gold, J. Am. Pharm. Assoc. 31 (1942) 306.
- 421 G. Maffii, G. Schott, M. G. Serralunga, Res. Prog. Org. Biol. Med. Chem. 2 (1970) 262.
- 422 Y. Kawaguchi et al., Iyakuhin Kenkyu 11 (1980) 635. Kaken Chemical, JP 52083940, 1976 (S. Suzuki). P. Gullino et al., Arch. Biochem. Biophys. 64 (1956) 319. Degussa, unpublished, 1981 and 1982. E.-J. Kirnberger et al., Arzneim. Forsch. 8 (1958) 72.
Further Reading
- K. Araki, T. Ozeki: Amino Acids, Kirk Othmer Encyclopedia of Chemical Technology, 5th edition, vol. 2, p. 554–618, John Wiley & Sons, Hoboken, NJ, 2004, online: DOI: 10.1002/0471238961.1921182201180111.a01.pub2 (July 2003).
- M. A. Blaskovich: Handbook on Syntheses of Amino Acids, Oxford Univ. Press, New York 2010.
- L. A. Cynober (ed.): Metabolic and Therapeutic Aspects of Amino Acids in Clinical Nutrition, 2nd ed., CRC Press, Boca Raton, FL 2004.
-
J. P. D'Mello (ed.):
Amino Acids in Animal Nutrition,
2nd ed.,
CABI Publ,
Wallingford
2003.
10.1079/9780851996547.0000 Google Scholar
- R. Faurie, J. Thommel (eds.): Microbial Production of L-Amino Acids, Springer, Berlin 2002.
- A. B. Hughes (ed.): Amino Acids, Peptides and Proteins in Organic Chemistry, Vols. 1–6, Wiley-VCH, Weinheim 2009ff.
- V. F. Wendisch (ed.): Amino Acid Biosynthesis, Springer, Berlin 2007.
