Polyaspartic Acids
Part 7. Polyamides and Complex Proteinaceous Materials
Dr. Winfried Joentgen,
Dr. Nikolaus Müller,
Dr. Alfred Mitschker,
Dr. Holger Schmidt,
Dr. Winfried Joentgen
- [email protected]
- +49 202/36-2661 | Fax: +49 202/36-2566
Bayer AG, Wuppertal, Germany, 42096
Search for more papers by this authorDr. Nikolaus Müller
- [email protected]
- +49 214/30-65962 | Fax: +49 214/30-72098
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorDr. Alfred Mitschker
- [email protected]
- +49 214/30-54043 | Fax: +49 214/30-81079
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorDr. Holger Schmidt
- [email protected]
- +49 214/30-61318 | Fax: +49 214/30-81079
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorDr. Winfried Joentgen,
Dr. Nikolaus Müller,
Dr. Alfred Mitschker,
Dr. Holger Schmidt,
Dr. Winfried Joentgen
- [email protected]
- +49 202/36-2661 | Fax: +49 202/36-2566
Bayer AG, Wuppertal, Germany, 42096
Search for more papers by this authorDr. Nikolaus Müller
- [email protected]
- +49 214/30-65962 | Fax: +49 214/30-72098
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorDr. Alfred Mitschker
- [email protected]
- +49 214/30-54043 | Fax: +49 214/30-81079
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorDr. Holger Schmidt
- [email protected]
- +49 214/30-61318 | Fax: +49 214/30-81079
Bayer AG, Leverkusen, Germany, 51368
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Chemical Structure
- Chemical Analysis
- 1H-NMR Spectroscopy
- 13C-NMR Spectroscopy
- 15N-NMR Spectroscopy
- Gel-permeation Chromatography
- Isotachophoresis
- Detection in Technical Applications
- Fluorescence Spectroscopy
- Precipitation Titration
- Polyelectrolyte Titration
- Biodegradation
- Production of PASP
- World Market and Applications
- Patents
- Outlook and Perspectives
References
- Addadi, L., Weiner, S. (1992) Kontroll- und Designprinzipien bei der Biomineralisation, Angew. Chem. Int. Ed. Engl. 31, 153–169.
- Adler, D. E., Freeman, M. B., Lipovsky, J. M., Paik, Y. H. (1995) Acid catalyzed process for preparing amino acid copolymers, Rohm and Haas Company, US Patent 5 457 176.
- Alford, D. D., Wheeler, A. P., Pettigrew, C. A. (1994) Biodegradation of thermally synthesized polyaspartate, J. Environ. Polymer Degrad. 2, 225–236.
- Allemand, D., Cuif, J.-P. (1994) Biomineralisation 93, 7th International Symposium of Biomineralization. Bulletin de l'institut oceánographique Monaco, 5–10.
- Angrick, M., Rewicki, D. (1980) Chemie in unserer Zeit 14, 149–157.
- Dessaignes, M. (1850) Nouvelles recherches sur la production de l'acide succinique au moyen de la fermentation, C. R. Seances 31, 432–433.
- Doi, Y., Tabata, K., Abe, H. (2000) Microbial degradation of poly(aspartic acid) by two isolated strains of Pedobacter sp. and Sphingomonas sp., Biomacromolecules 1, 157–161.
- Domard, A., Rinaudo, M. (1981) Polyelectrolyte complexes: interaction between poly(l-lysine) and polyanions with various charge densities and degrees of polymerization, Macromolecules 14, 620–625.
- Elias, G. E. (1997) An Introduction to Polymer Science, Weinheim, New York: Verlag Chemie, 120–127.
- European Eco-label, (1992) http://europa.eu.int./ecolabel.
- Everaerts, F. M., Verheggen, T. P., Mikkers, F. E. (1979) Determination of substances at low concentrations in complex mixtures by isotachophoresis with column coupling, J. Chromatogr. 169, 21–38.
- Eyal, A., Cami, P. (1997) Process for the preparation of aspartic acid, Amylum, WO/ 97 27312.
-
Fizwater, S.
(1995)
Computer simulation of polyelectrolyte adsorption on mineral surface,
ACS Symp. Ser. 589,
316–325.
10.1021/bk-1995-0589.ch023 Google Scholar
- Fox, S. W., Harada, K. (1960a) Thermal copolymerization of amino acids in the presence of phosphoric acid, Arch. Biochem. Biophys. 86, 281–285.
- Fox, S. W., Harada, K. (1960b) The thermal copolymerization of amino acids to protein, J. Amer. Chem. Soc. 82, 3745–3751.
- Fox, S. W., Harada, K., Vegotsky, A. (1959) Thermal polymerization of amino acids and a theory of biochemical origins, Experientia 15, 81–84.
- Fox, S. W., Harada, K., Krampitz, G., Mueller, G. (1970) Chemical origins of cells, Chem. Eng. News 48, 80–94.
- Freeman, M. B., Paik, Y. H., Swift, G., Wilczynski, R., Wolk, S. K., Yocom, K. M. (1994) Biodegradability of polycarboxylates: structure–activity studies, Polym. Prep. (Am. Chem. Soc.) 35, 423–424
- Freeman, M. B., Swift, G., Paik, Y. H., Wilczynski, R., Wolk, S. K., Yokom, K. (1996) Biodegradability of polycarboxylates: structure–activity studies, in: Hydrogels and Biodegradable Polymers for Bioapplications ( R. M. Ottenbrite, S. J. Huang, K. Park, Eds.), Washington, DC: American Chemical Society, Chapter 10, 118–136.
- Gonsalves, K. E., Mungara, P. M. (1996) Synthesis and properties of degradable polyamides and related polymers, Trends Polym. Sci. 4, 25–31.
- Goto, A., Kunioka, M. (1992) Effective fermentation of poly(gamma-glutamic acid) from a medium containing citric acid, Polymer Reprints 41, 217–219.
- Harada, K. (1959) Polycondensation of thermal precursors of aspartic acid, J. Org. Chem. 24, 1662–1666.
- Harada, K., Fox, S. W. (1964) Thermal polycondensation of free amino acids with polyphosphoric acid, Principles Med. Biol. 1, 289.
- Heise, K.P., Wendt, H. (2000) Method for the quantitative determination of poly aspartic acid, Bayer AG, WO 00/28305.
- Horn, D. (1980) Polymeric Amines and Ammonium Salts, ( E. J. Goethals, Ed.), Oxford, New York: Pergamon Press, 333.
- Kaniansky, D., Havasi, P. (1983) Instrumentation for capillary isotachophoresis, Trends Anal. Chem. 2, 197–202.
-
Karsa, D. R.,
Porter, M. R. (Eds.)
(1995)
Biodegradability of Surfactants, Glasgow: Blackie,
95–97.
10.1007/978-94-011-1348-9 Google Scholar
- Koskan, L. P., Low, K. C., Meah, A., Atencio, A. M., (1995) Polyaspartic acid manufacture, Donlar Corporation, WO 95/00479.
- Kovacs, J., Könyves, I. (1954) Über dl-α,β-Polyasparaginsäure, Naturwissenschaften 41, 333.
- Kovacs, J., Könyves, I., Pusztai, A. (1953) Über dl-α, β-Polyasparaginsäure, Experientia 9, 459–460.
- Kurshwaha, D. R. S. (1980) Poly-ɛ-lysine: synthesis and conformation, Biopolymers 19, 219–229.
- Larson, R. J., Bookland, E. A., Williams, R. T., Yocom, K. M., Saucy, D. A., Freeman, M. B., Swift, G. (1997) Biodegradation of acrylic acid polymers and oligomers by mixed microbial communities in activated sludge, J. Environ. Polym. Degrad. 5, 41– 48.
- Low, K. C., Wheeler, A. P., Koskan, L. P. (1996) Commercial poly(aspartic acid) and its uses, Adv. Chem. Ser. 248, 99–111.
- Mann, S. J. (1993) Biomineralization: the hard part of bioinorganic chemistry, J. Chem. Soc., Dalton Trans. 1993, 1–9.
- Matsubara, K, Nakato, T., Tomida, M. (1997) 1H and 13C NMR characterization of polysuccinimide prepared by thermal condensation of l-aspartic acid, Macromolecules 30, 2305–2312.
- Matsuyama, M., Kokufuta, E., Kusumi, T., Harada, K. (1980) On the Poly(β-dl- aspartic acid), Macromolecules 13, 196–198.
- Meggy, A. B. (1956) Glycine peptides. II. Heat and entropy of formation of the peptide bond in polyglycine, J. Chem. Soc. 1956, 1444–1445.
- Miller, W. G. (1961) Degradation of Poly-α,l-glutamic Acid. I. Degradation of high molecular weight PGA by papain, J. Am. Chem. Soc. 83, 259–265.
- Miller, W. G. (1964a) Degradation of synthetic polypeptides. II. Degradation of poly-α, l-glutamic acid by proteolytic enzymes in 0.20 M sodium chloride, J. Am. Chem. Soc. 86, 3913–3922.
- Miller, W. G. (1964b) Dynamics of the helix-coil transition in poly-α,l-glutamic acid, Biopolymers 2, 489–500.
- Morall, S. W., Bookland, E. A., Larson, R. J., Rothgelb, T. M., Yocum, K. M., Swift, G. (1997) Biodegradation and chemical structure of synthetic polyaspartic acids, Gordon Research Conference, Barga, Italy, 5–9 May 1997, 1–14.
- Neri, P., Antoni, G., Benvenuti, F., Cocola, F., Gazzei, G. (1973) Synthesis of α,β-Poly[(2-hydroxyethyl)-dl-aspartamide], a new plasma expander, J. Med. Chem. 16, 893–897.
- Organization for Economic Cooperation and Development (1981) Guidelines for Testing of Chemicals.
- Pivcova, H., Saudek, V. (1985) Carbon-13C-NMR relaxation study of poly(aspartic acid), Polymer 26, 667–672.
- Pivcova, H., Saudek, V., Drobnik, J. (1981) NMR study of poly(aspartic acid). I. α- and β- peptide bonds in poly(aspartic acid) prepared by thermal polycondensation, Biopolymers 20, 1605–1614.
- Pivcova, H., Saudek, V., Drobnik, J. (1982) 13C n.m.r. study of the structure of poly(aspartic acid), Polymer 23, 1237–1241.
- Rao, V. S., Lapointe, P., McGregor, D. N. (1993) Synthesis of uniform polyaspartic acid, Makromol. Chem. 194, 1095–1104.
- Rusenko, K. W., Donachy, J. E., Wheeler, A. P. (1991) Purification and characterization of a shell matrix phosphoprotein from the American oyster, in: Surface Reactive Peptides and Polymers: Discovery and commercialisation ( C. S. Sikes, A. P. Wheeler, Eds.), Washington DC: ACS Books, 107–121.
- Sarig, S., Shifrin, F. (1977) The use of polymers for retardation of scale formation, National Counc. Res. Dev. [Rep] NCRD (Isr.), 150–157.
-
Schaal, E.
(1871)
Über einige aus Asparaginsäure entstehende Produkte,
Leibig's Annalen der Chemie 157,
24–34.
10.1002/jlac.18711570105 Google Scholar
- Schiff, H. (1897) Über Polyaspartsäuren, Chem. Ber. 30, 2449–2459.
- Schwamborn, M. (1996) Polyasparaginsäuren, Nachr. Chem. Tech. Lab. 44, 1167–1170.
- Schwamborn, M. (1997) Neue biologisch abbaubare Funktionspolymere, GDCH Umwelttagung Heidelberg.
- Schwamborn, M. (1998) Chemical synthesis of polyaspartates: a biodegradable alternative to currently used polycarboxylate homo- and copolymers, Polym. Degrad. Stab. 58, 39–45.
- Sikes, C. S., Wheeler, A. P. (1985) Inhibition of inorganic or biological CaCO3 deposits by poly amino acid derivatives, University of South Alabama, US Patent 4 534 881.
- Sikes, C. S., Wheeler, A. P. (Eds.) (1988) Chemical aspects of regulation of mineralization. Proceedings of a Symposium sponsored by the Division of Industrial and Engineering Chemistry of the American Chemical Society, New Orleans, September 3–4, 1987.
- Sikes, C. S., Wierzbicki, A. (1994) Mechanistic studies of polyamino acids as antiscalants, Corrosion, 94, Paper No. 193, 1–19.
- Sikes, C. S., Wierzbicki, A. (1996) Biomimetic material chemistry, in: Polyamino Acids as Antiscalants, Dispersants, Antifreezes, and Absorbent Gelling Material ( S. Mann, Ed.), New York: Verlag Chemie, Chapter 9, 249–278.
- Sikes, C. S., Yeung, M. L., Wheeler, A. P. (1991) Inhibition of calcium carbonate and phosphate crystallization by peptides enriched in aspartic acid and phosphoserine, in: Surface Reactive Peptides and Polymers: Discovery and commercialisation ( C. S. Sikes, A. P. Wheeler, Eds.), ACS Symposium Series, Washington DC: ACS Books, 50–71.
- Stetler-Stevenson, W. G., Veis, A. (1983) Bovine dentin phosphophoryn: composition and molecular weight, Biochemistry 22, 4326–4335.
- Swedish Society for Nature Conservation (SSNC) (2001) http://www.SNF.se.
- Wagner, P., Döbert, F., Menzel, T., Groth, T., Joentgen, W., Liesenfelder, U., Weinschenck, J., Heise, K. P. (1998) Method for carrying out polycondensation reactions, Bayer AG, US Patent 6 187 898.
- Wassmer, K. H., Schroeder, U., Horn, D. (1991) Characterization and detection of polyanions by direct polyelectrolyte titration, Makromol. Chem. 192, 553–565.
- Wheeler, A. P., Rusenko, K. W., Swift, D. M., Sikes, C. S. (1988) Regulation of in vitro and in vivo calcium carbonate crystallization by fractions of oyster shell organic matrix, Mar. Biol. 98, 71–80.
- Wierzbicki, A., Sikes, C. S., Madura, J. D., Drake, B. (1994) Atomic force microscopy and molecular modeling of protein and peptide binding to calcite, Calcif. Tissue Int., 54, 133–141.
- Wolff, J. (1850) Über Asparaginsäure aus Äpfelsäure, Ann. 75, 293–297.
- Wolk, S. K., Swift, G., Paik, Y. H., Yokom, K. M., Smith, R. L., Simon, E. S. (1994) One- and two-dimensional nuclear magnetic resonance characterization of poly(aspartic acid) prepared by thermal polymerization of l-aspartic acid, Macromolecules 27, 7613–7620.
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