Modifications of Proteins and Poly(amino acids) by Enzymatic and Chemical Methods
Part 7. Polyamides and Complex Proteinaceous Materials
Dr. Kousaku Ohkawa,
Prof. Dr. Hiroyuki Yamamoto,
Dr. Kousaku Ohkawa
- [email protected]
- +81-268-215573 | Fax: +81-268-215571
Shinshu University, Institute of High Polymer Research, Faculty of Textile Science and Technology, Ueda, Japan, 386-8567
Search for more papers by this authorProf. Dr. Hiroyuki Yamamoto
- [email protected]
- +81-268-215572 | Fax: +81-268-215571
Shinshu University, Institute of High Polymer Research, Faculty of Textile Science and Technology, Ueda, Japan, 386-8567
Search for more papers by this authorDr. Kousaku Ohkawa,
Prof. Dr. Hiroyuki Yamamoto,
Dr. Kousaku Ohkawa
- [email protected]
- +81-268-215573 | Fax: +81-268-215571
Shinshu University, Institute of High Polymer Research, Faculty of Textile Science and Technology, Ueda, Japan, 386-8567
Search for more papers by this authorProf. Dr. Hiroyuki Yamamoto
- [email protected]
- +81-268-215572 | Fax: +81-268-215571
Shinshu University, Institute of High Polymer Research, Faculty of Textile Science and Technology, Ueda, Japan, 386-8567
Search for more papers by this authorFirst published: 15 January 2005
Abstract
- Introduction
- Naturally Occurring Cross-linked Materials
- Keratin, Collagen, and Elastin
- Structural Proteins in Invertebrate Bodies
- Insect Cuticles and Eggshells
- Byssus of Mussels
- Isopeptide Cross-linking of Cellular Proteins
- Enzymes Involved in the Protein Cross-links
- Lysyl Oxidase
- Tyrosinase
- Transglutaminase
- Chemical Cross-linking
- Bifunctional Cross-linking Reagents
- Oxidants
- Photo-Induced Cross-linking – Photodimerization of Polypeptide Side Chain
- Noncovalent Cross-linking – Electrostatic Force Interaction
- Material Science of Cross-linked Proteins and Poly(amino acids)
- Cross-linked Hydrogels
- Polyion Complex Material Formulations
- Capsules
- Fibers
- Medical Adhesives
- Outlook and Perspectives
- Acknowledgments
References
- Aeschlimann, D., Thomazy, V. (2000) Protein cross-linking in assembly and remodelling of extracellular matrices: The role of transglutaminases, Connect. Tissue Res. 41, 1–27.
- Anderson, S. O. (1963) Characterization of a new type of cross-linkage in resilin, a rubber like protein, Biochim. Biophys. Acta 69, 249–262.
- Anet, R. (1962) The photodimers of coumarin and related compounds, Can. J. Chem. 40, 1249–1257.
- Arnold, L. J., Dagan, A., Gutheil, J., Kaplan, N. O. (1979) Antineoplastic activity of poly(l-lysine) with some ascites tumor cells, Proc. Natl. Acad. Sci. USA. 76, 3246–3250.
- Arnow, L. E. (1937) Colorimetric determination of the components of 3,4-dihydroxyphenylalanine-tyrosine mixtures, J. Biol. Chem. 118, 351–357.
- Bailey, A. J., Peach, C. M. (1968) Isolation and structural identification of a labile intermolecular cross-link in collagen, Biochem. Biophys. Res. Commun. 33, 812–819.
- Ballard, D. G. H. (1968) Synthetic polypeptides, in: Man-Made Fibers: Science and Technology, Vol. 2, ( H. F. Mark, S. M. Atlas, E. Cernia, Eds.), New York: John Wiley & Sons, 401–433.
- Bamford, C. H., Elliott, A., Hanby, W. E. (1956) Synthetic Polypeptides, New York: Academic Press.
- Bhattacharyya, D., Hestekin, J. A., Brushaber, P., Cullen, L., Bachas, L. G., Skidar, S. K. (1998) Novel poly-glutamic acid functionalized microfiltration membranes for sorption of heavy metals at high capacity, J. Membrane Sci. 141, 121–135.
-
Borysko, E.
(1963)
Collagen, in: Ultrastructure of Protein Fibers ( R. Borasky, Ed.), New York: Academic Press,
19–37.
10.1016/B978-1-4832-2838-9.50009-X Google Scholar
- Bronich, T. K., Cherry, T., Vinogradov, S. V., Eisenberg, A., Kabanov, V. A., Kabanov, A. V. (1998) Self-assembly in mixtures of poly(ethyleneoxide)-graft-poly(ethyleneimine) and alkyl sulfates, Langmuir 14, 6101–6106.
- Brown, B. R. (1967) Biochemical aspects of oxidative coupling of phenols, in: Oxidative Coupling of Phenols ( W. I. Taylor, A. R. Battersby, Eds.), New York: Marcel Dekker, 167–201, Vol. 1.
- Brown, C. H. (1950) A review of the methods available for the determination of the types of forces stabilizing structural proteins in animals, Q. J. Microsc. Sci. 91, 331–339.
- Burton, A. C. (1954) Relation of structure to function of the tissues of the wall of blood vessels, Physiol. Rev. 34, 619–642.
- Burzio, L. A., Waite, J. H. (2000) Cross-linking in adhesive quinoproteins: Studies with model decapeptides, Biochemistry 39, 11147–11153.
- Burzio, L. O., Gutierrez, E., Pardo, J., de la Fuente, E., Brito, M., Saez, C. (1990) Bioadhesives: A biotechnological opportunity, Arch. Biol. Med. Exp. 23, 173–178.
- Carlini, C., Fissi, A., Galletti, A. M. R., Sbrana, G. (2000) Optically active polymers bearing side-chain photochromic moieties: Synthesis and chiroptical properties of methacrylic homopolymers with pendant trans-azobenzene chromophores bound through l-leucine, l-valine and l-proline amino acid spacers, Macromol. Chem. Phys. 201, 1540–1551.
- Carroll-Porczynski, C. Z. (1961) Natural Polymer Man-Made Fibres, London: National Trade Press.
- Ciechanover, A. (1994) The ubiquitin-proteasome proteolytic pathway, Cell 79, 13–21.
-
Coqueret, X.
(1999)
Photoreactivity of polymers with dimerizable side-groups: Kinetic analysis for probing morphology and molecular organization,
Macromol. Chem. Phys. 200,
1567–1579.
10.1002/(SICI)1521-3935(19990701)200:7<1567::AID-MACP1567>3.0.CO;2-9 CAS Web of Science® Google Scholar
- DeVore, D. P., Gruebel, R. J. (1978) Dityrosine in adhesive formed by the sea mussel, Mytilus edulis, Biochem. Biophys. Res. Commun. 80, 993–999.
-
Dikie, R.,
Labana, S.,
Bauer, R. (Eds.)
(1988)
Cross-linked Polymers, Washington, DC: American Chemical Society.
10.1021/bk-1988-0367 Google Scholar
- Fasman, G. D. (Ed.) (1967) Poly-α-Amino Acids: Protein Models for Conformational Studies, New York: Marcel Dekker.
- Folk, J. E., Cole, P. W. (1966) Mechanism of action of guinea pig liver transglutaminase. I. Purification and properties of the enzyme: Identification of a functional cysteine essential for activity, J. Biol. Chem. 241, 5518–5525.
- Francis, G., John, R., Thomas, J. (1973) Biosynthesis pathway of desmosines in elastin, Biochem. J. 136, 45–55.
-
Frank, R.,
Jakob, M.,
Thunecke, F.,
Fischer, G.,
Schutowski, M.
(2000)
Thioxylation as one-atom-substitution generates a photoswitchable element within the peptide backbone,
Angew. Chem. Int. Edn. 39,
1120–1122.
10.1002/(SICI)1521-3773(20000317)39:6<1120::AID-ANIE1120>3.0.CO;2-H CAS PubMed Web of Science® Google Scholar
- Franzblau, C., Sinex, F. M., Faris, B., Lampidis, R. (1965) Identification of a new cross-linking amino acid in elastin, Biochem. Biophys. Res. Commun. 21, 575–581.
- Franzblau, C. (1970) Elastin, in Comprehensive Biochemistry, Vol. 26, Part C ( M. Florkin, E. H. Stotz, Eds.), Amsterdam: Elsevier, 659–712.
- Gibson, W. (1992) Gellan gum, in: Thickening and Gelling Agents for Food ( A. Imeson, Ed.), London: Chapman & Hall, 227–249.
- Gross, A. J., Sizer, I. W. (1959) The oxidation of tyramine, tyrosine, and related compounds by peroxidase, J. Biol. Chem. 234, 1611–1614.
- Hackman, R. H., Todd, A. R. (1953) Some observations on the reaction of catechol derivatives with amines and amino acids in presence of oxidizing agents, Biochem. J. 55, 631–637.
- Hammond, G. S., Stout, C. A., Lamola, A. A. (1964) Mechanisms of photochemical reactions in solution. XXV. The photodimerization of coumarin, J. Am. Chem. Soc. 86, 3103–3106.
- Hoeve, C. A. J., Flory, P. J. (1958) The elastic properties of elastin, J. Am. Chem. Soc. 80, 6523–6526.
- Housley, T., Tanzer, M. L., Henson, E., Gallop, P. M. (1975) Collagen cross-linking: Isolations of hydroxyaldol-histidine, a naturally-occurring cross-link, Biochem. Biophys. Res. Commun. 67, 824–830.
- Hwang, J. J., Stupp, S. I. (2000) Poly(amino acid) bioadhesives for tissue repair, J. Biomater. Sci. Polym. Ed. 11, 1023–1038.
- Imai, Y., Ogoshi, T., Naka, K., Chujo, Y. (2000) Formation of IPN organic-inorganic polymer hybrids utilizing the photodimerization of thymine, Polym. Bull. 45, 9–16.
- Ito, S., Fujita, K. (1981) Formation of cysteine conjugates from dihydroxyphenylalanine and its S-cysteinyl derivatives by peroxidase-catalyzed oxidation, Biochim. Biophys. Acta 672, 151–157.
- Iwata, H., Matsuda, S., Mitsuhashi, K., Itoh, E., Ikada, Y. (1998) A novel surgical glue composed of gelatin and N-hydroxysuccinimide activated poly(l-glutamic acid): Part 1. Synthesis of activated poly(l-glutamic acid) and its gelation with gelatin, Biomaterials 19, 1869–1876.
- Kabanov, A. V., Kabanov, V. A. (1995) DNA complexes with polycations for the delivery of genetic material into cells, Bioconjug. Chem. 6, 7–20.
- Kagan, H. M., Sullivan, K. A. (1982) Lysyl oxidase: Preparation and role in elastin biosynthesis, Methods. Enzymol. 82, 637–650.
-
Kertesz, D.,
Zito, R.
(1962)
Phenolase, in: Oxygenases ( O. Hayashi, Ed.), New York: Academic Press,
307–354.
10.1016/B978-1-4832-3234-8.50012-5 Google Scholar
- Kerwin, J. L., Whitney, D. L., Sheikh, A. (1999) Mass spectrometric profiling of glucosamine, glucosamine polymers and their catecholamine adducts. Model reactions and cuticular hydrolysates of Toxorhynchites amboinensis (Culicidae) pupae, Insect. Biochem. Mol. Biol. 29, 599–607.
- Koehnlein, H. E., Lemperle, G. (1969) Experimental studies with a new gelatin-resorcin-formaldehyde glue, Surgery 66, 377–382.
- Krauch, C. H., Farid, S., Schenck, G. O. (1966) Photo-C4-cyclodimersation von Cumarin, Chem. Ber. 99, 625–633.
- Krylov, A. V., Kotova, E. A., Yaroslavov, A. A., Antonenko, Y. N. (2001) Stabilization of O-pyromellitylgramicidin channels in bilayer lipid membranes through electrostatic interaction with polylysines of different chain lengths, Biochim. Biophys. Acta 1509, 373–385.
- Kumer, G., Bristow, J. F., Smith, P. J., Payne, G. F. (2000) Enzymatic gelation of the natural polymer chitosan, Polymer 41, 2157–2168.
-
Labana, S.,
Dickie, R. (Eds.)
(1984)
Characterization of Highly Cross-linked Polymers, Washington, DC: American Chemical Society.
10.1021/bk-1984-0243 Google Scholar
- Lindner, E., Dooley, C. (1973) Chemical bonding in cirriped adhesive, in: Proceedings 3rd International Congress on Marine Corrosion and Fouling, Evanston, IL: Northwestern University Press, 653–673.
- Lorand, L., Conrad, S. M. (1984) Transglutaminases, Mol. Cell. Biochem. 58, 9–35.
- Lucas, J. M., Vaccaro, E., Waite, J. H. (2003) Extra-organismic adhesive proteins, in: Biopolymers ( S. Fahnestock, A. Steinbüchel, Eds.), Weinheim, Germany: Wiley-VCH, Vol. 7/8.
-
Lundgren, H. P.,
Ward, W. H.
(1963)
The keratins, in: Ultrastructure of Protein Fibers ( R. Borasky, Ed.), New York: Academic Press,
39–122.
10.1016/B978-1-4832-2838-9.50010-6 Google Scholar
- Margolin, A. L., Sherstyuk, S. F., Izumrudov, V. A., Zezin, A. B., Kabanov, V. A. (1985) Enzymes in polyelectrolyte complexes. The effect of phase transition on thermal stability, Eur. J. Biochem. 146, 625–632.
- Mita, K., Zama, M., Ichimura, S. (1977) Effect of charge density of cationic polyelectrolytes on complex formation with DNA, Biopolymers 16, 1993–2004.
- Mitsuki, M., Mizuno, A., Tanimoto, H., Motoki, M. (1998) Relationships between the antifreeze activities and the chemical structures of oligo- and poly(glutamic acid)s, J. Agricul. Food Chem. 46, 891–895.
- Mo, X., Iwata, H., Matsuda, S., Ikada, Y. (2000) Soft tissue adhesive composed of modified gelatin and polysaccharides, J. Biomater. Sci. Polym. Ed. 11, 341–351.
- Morrison, H., Curtis, H., McDowell, T. (1966) Solvent effects on the photodimerization of coumarin, J. Am. Chem. Soc. 88, 5415–5419.
- Muzzarelli, R. A. A. (1977) Chitin, Oxford: Pergamon.
- Musierowicz, A. (1976) Use of tissue glue (butyl-2-cyanacrylate) for creation of loop ureterostomy, Pol. Przegl. Chir. 48, 203–204.
- Mustafa, A. (1952) Dimerization reactions in sunlight, Chem. Rev. 51, 1–23.
- Nagai, A., Yamamoto, H. (1989) Insolubilizing studies of water-soluble poly(Lys Tyr) by tyrosinase, Bull. Chem. Soc. Jpn. 62, 2410–2412.
- Noguchi, J., Tokura, S., Nishi, N. (1972) Poly-α-amino acid fibers, Angew. Makromol. Chem. 22, 107–131.
- Ohkawa, K., Nishida, A., Ichimiya, K., Matsui, Y., Nagaya, K., Yuasa, A., Yamamoto, H. (1999) Purification and characterization of a dopa-containing protein from foot of the Asian freshwater mussel, Limnoperna fortunei, Biofouling 14, 181–188.
- Ohkawa, K., Yamada, M., Nishida, A., Nishi, N., Yamamoto, H. (2000) Biodegradation of chitosan-gellan and poly(l-lysine)-gellan polyion complex fibers by pure-culture of soil filamentous fungi, J. Polym. Environ. 8, 59–66.
- Ohkawa, K., Fujii, K., Nishida, A., Yamauchi, T., Ishibashi, H., Yamamoto, H. (2001a) Lysyl oxidase-catalyzed cross-linking and insolubilization reactions of Lys-containing polypeptides and synthetic adhesive proteins, Biomacromolecules 2, 773–779.
- Ohkawa, K., Shoumura, K., Yamada, M., Nishida, A., Shirai, H., Yamamoto, H. (2001b) Photoresponsive peptide and polypeptide systems. 14: Biodegradation of photocross-linkable copolypeptide hydrogels containing l-ornithine and δ-7-coumaryloxuacetyl-l-ornithine residues, Macromol. Biosci. 1, 149–156.
- Ohkawa, K., Takahashi, Y., Yamada, M., Yamamoto, H. (2001c) Polyion complex fiber and capsule formed by self-assembly of chitosan and poly(α,l-glutamic acid) at solution interface, Macromol. Mater. Eng. 286, 168–175.
-
Ono, K.,
Saito, Y.,
Yura, H.,
Ishikawa, K.,
Kurita, A.,
Akaike, T.,
Ishihara, M.
(2000)
Photocross-linkable chitosan as a biological adhesive,
J. Biomed. Mater. Res. 49,
289–295.
10.1002/(SICI)1097-4636(200002)49:2<289::AID-JBM18>3.0.CO;2-M CAS PubMed Web of Science® Google Scholar
- Ooka, A. A., Garrell, R. L. (2000) Surface-enhanced Raman spectroscopy of DOPA-containing peptides related to adhesive protein of marine mussel, Mytilus edulis, Biopolymers 57, 92–102.
- Partridge, S. M., Elsden, D. F., Thomas, J. (1963) Constitution of the cross-linkages in elastin, Nature 197, 1297–1298.
- Paz, M. A., Flückiger, R., Boak, A., Kagan, H. M., Gallop, P. M. (1991) Specific detection of quinoproteins by redox-cycling staining, J. Biol. Chem. 266, 689–692.
- Pinnell, S. R., Martin, G. R. (1968) The cross-linking of collagen and elastin: Enzymatic conversion of lysine in peptide linkage to α-aminoadipic-δ-semialdehyde (allysine) by an extract from bone, Proc. Natl. Acad. Sci. USA. 61, 708–716.
- Pomerantz, S. H. (1964) Tyrosine hydroxylation catalyzed by mammalian tyrosinase: An improved method of assay, Biochem. Biophys. Res. Commun. 16, 188–194.
- Pryor, M. G. M. (1940) On the handling of the ootheca of Blatta orientalis, Proc. Royal Soc. London B. 128, 378–393.
- Pujol, J. P. (1970) The collagen of the byssus in Mytilus edulis L. II. Autoradiographic study on the incorporation of 3H-proline, Z. Zellforsch Mikrosk Anat. 104, 358–374.
- Ramsay, E., Hadgraft, J., Birchall, J., Gumbleton, M. (2000) Examination of the biophysical interaction between plasmid DNA and the polycations, polylysine and polyornithine, as a basis for their differential gene transfection in-vitro, Int. J. Pharmaceutics 210, 97–108.
- Ravindranath, M. H., Ramalingam, K. (1972) Histochemical identification of dopa, dopamine and catechol in the phenol gland and the mode of tanning of byssus threads of Mytilus edulis, Acta Histochem. 42, 87–94.
- Reihmann, M. H., Ritter, H. (2000) Enzymatically catalyzed synthesis of photocross-linkable oligophenols, Macromol. Chem. Phys. 201, 1593–1598.
- Richards, A. N., Gies, W. J. (1902) Chemical studies of elastin, mucoid, and other proteids in elastic tissue, with some notes on ligament extractives, Am. J. Physiol. 7, 93–134.
- Sakharov, D. V., Jie, A. F. H., Bekkers, M. E. A., Emeis, J. J., Rijken, D. C. (2001) Polylysine as a vehicle for extracellular matrix-targeted local drug delivery, providing high accumulation and long-term retention within the vascular wall, Arteiosclerosis Thrombosis and Vascular Biology 21, 943–948.
- Schaefer, J., Kramer, K. J., Garbow, J. R., Jacobs, G. S., Stejskal, E. O., Hopkins, T. L., Speirs, R. D. (1987) Aromatic cross-links in insect cuticle: Detection by solid state 13C and 15N NMR, Science 235, 1200–1204.
- Sekine, T., Nakamura, T., Shimizu, Y., Ueda, H., Matsumoto, K., Takimoto, Y., Kiyotani, T. (2001) A new type of surgical adhesive made from porcine collagen and polyglutamic acid, J. Biomed. Mater. Res. 54, 305–310.
- Shen, W. C., Ryser, H. J., LaManna, L. (1985) Disulfide spacer between methotrexate and poly(d-lysine). A probe for exploring the reductive process in endocytosis, J. Biol. Chem. 260, 10905–10908.
- Siegel, R. C., Pinnell, S. R., Martin, G. R. (1970) Cross-linking of collagen and elastin. Properties of lysyl oxidase, Biochemistry 9, 4486–4492.
- Silman, H. I., Sela, M. (1967) Biological properties of poly-α-amino acids, in: Poly-α-Amino Acids: Protein Models for Conformational Studies ( G. D. Fasman, Ed.), New York: Marcek Dekker, 605–673.
- Smith-Mungo, L. I., Kagan, H. M. (1998) Lysyl oxidase: Properties, regulation and multiple functions in biology, Matrix Biol. 16, 387–398.
- Sperinde, J. J., Griffith, L. G. (1997) Synthesis and characterization of enzymatically-cross-linked poly(ethylene glycol) hydrogel, Macromolecules 30, 5255–5264.
- Stahman, M. A. (Ed.) (1962) Polyamino Acids: Peptides and Proteins, Madison: The University of Wisconsin Press.
- Sugumaran, M. (1988) Molecular mechanisms for cuticular sclerotizaion, in: Advances in Insect Physiology ( P. Evans, V. Wigglesworth, Eds.), London: Academic Press, 179–231, Vol. 21.
- Sung, H. W., Huang, D. M., Chang, W. H., Huang, L. L., Tsai, C. C., Liang, I. L. (1999) Gelatin-derived bioadhesives for closing skin wounds: An in vivo study, J. Biomater. Sci. Polym. Ed. 10, 751–771.
- Takahashi, Y., Ohkawa, K., Ando, M., Yamada, M., Yamamoto, H. (2001) Adsorption of endocrine disruptors and related compounds using natural polymer composite fibers formed by polyion complex, Macromol. Mater. Eng. 286, 733– 736.
-
Tanzer, M. L.
(1976)
Cross-linking, in: Biochemistry of Collagen ( G. N. Ramachandran, A. H. Reddi, Eds.), New York: Plenum,
137–162.
10.1007/978-1-4757-4602-0_4 Google Scholar
- Tanzer, M. L., Waite, J. H. (1982) Collagen cross-linking, Collagen Rel. Res. 2, 177–180.
- Tatehata, H., Mochizuki, A., Kawashima, T., Yamashita, S., Yamamoto, H. (2000) Model polypeptide of mussel adhesive protein I. Synthesis and adhesive studies of sequential polypeptides (X-Tyr-Lys)n and (Y-Lys)n, J. Appl. Polym. Sci. 76, 929–937.
- Tatehata, H., Mochizuki, A., Ohkawa, K., Yamada, M., Yamamoto, H. (2001) Tissue adhesive using synthetic model adhesive proteins inspired by the marine mussel, J. Adhesion Sci. Technol. 15, 1003–1013.
- Thomas, J., Elsden, D. F., Partridge, S. M. (1963) Partial structure of two major degradation products from the cross-linkages in elastin, Nature 200, 651–652.
- Trackman, P. C., Zoski, C. G., Kagan, H. M. (1981) Development of a peroxidase-coupled fluorometric assay for lysyl oxidase, Anal. Biochem. 113, 336–342.
- Vithayathil, P. J., Murthy, G. S. (1972) New reaction of o-benzoquinone at the thioether group of methionine, Nature 236, 101–103.
- Waite, J. H., Benedict, C. V. (1984) Assay of dihydroxyphenylalanine (Dopa) in invertebrate structural proteins, Method Enzymol. 107, 397–413.
- Waite, J. H., Tanzer, M. L. (1980) The bioadhesive of Mytilus byssus: A protein containing l-dopa, Biochem. Biophys. Res. Commun. 96, 1554–1561.
- Waite, J. H., Qin, X. X., Coyne, K. J. (1998) The peculiar collagens of mussel byssus, Matrix Biol. 17, 93–106.
- Weis-Fogh, T. (1960) A rubber-like protein in insect cuticle, J. Exp. Biol. 37, 889–906.
- Winder, A. J., Harris, H. (1991) New assays for the tyrosine hydroxylase and dopa oxidase activities of tyrosinase, Eur. J. Biochem. 198, 317–326.
- Wormell, R. L. (1954) New Fibres from Proteins, London: Butterworths Scientific Publications.
- Yagi, K., Nagatsu, T. (1960) Condensation products of ethylenediamine with catechol derivatives, J. Biochem. 48, 439–452.
- Yamada, K., Chen, T., Kumar, G., Vesnovsky, O., Topoleski, L. D., Payne, G. F. (2000) Chitosan based water-resistant adhesive. Analogy to mussel glue, Biomacromolecules 1, 252–258.
- Yamamoto, H. (1987a) Adhesion studies of synthetic polypeptides: a model for marine adhesive proteins, J. Adhesion Sci. Technol. 1, 177–183.
- Yamamoto, H. (1987b) Synthesis and adhesive studies of marine polypeptides, J. Chem. Soc. Parkin Trans I, 613–618.
- Yamamoto, H. (1996a) Marine adhesive protein, Synthetic, in: The Polymeric Materials Encyclopedia ( J. Salamone, Ed.), Boca Raton, Florida: CRC Press, 4025–4032, Vol. 6.
- Yamamoto, H. (1996b) Marine adhesive proteins and some biotechnological applications, in: Biotechnology & Genetic Engineering Reviews ( M. Tombs, Ed.), Andover: Intercept, 133–165, Vol. 13.
- Yamamoto, H., Ohkawa, K. (2002) Polypeptide behavior at interfaces, in: Encyclopedia of Surface and Colloid Science ( A. Hubbard, Ed.), New York: Marcel Dekker, 4242–4254.
- Yamamoto, H., Senoo, Y. (2000) Polyion complex fiber and capsule formed by self-assembly of chitosan and gellan at solution interfaces, Macromol. Chem. Phys. 201, 84–92.
- Yamamoto, H., Tanisho, H. (1993) Gel formation and its properties as hydrogel of cross-linked lysine polypeptides using organic cross-linking agents, Mater. Sci. Eng. C1, 45–51.
- Yamamoto, H., Kitsuki, T., Nishida, A., Asada, K., Ohkawa, K. (1999) Photoresponsive peptide and polypeptide systems. 13. Photo-induced cross-linked gel and biodegradation properties of copoly(l-lysine) containing ɛ-7-coumaryloxyacetyl-l-lysine residues, Macromolecules 32, 1055–1061.
- Yamamoto, H., Horita, C., Senoo, Y., Nishida, A., Ohkawa, K. (2001) Polyion complex fiber and capsule formed by self-assembly of poly-l-lysine and gellan at solution interfaces, J. Appl. Polym. Sci. 79, 437–446.
- Yu, A.-M., Chen, H.-T. (1997) Electrocatalytic oxidation and determination of ascorbic acid at poly(glutamic acid) chemically modified electrotode, Anal. Chim. Acta 344, 181–187.
- Yu, M., Deming, T. J. (1998) Synthetic polypeptide mimics of marine adhesives, Macromolecules 31, 4739–4745.
- Zhang, X., Collins, L., Sawyer, G. J., Dong, X., Qiu, Y., Fabre, J. W. (2001) In vivo gene delivery via portal vein and bile duct to individual lobes of rat liver using a polylysine-based nonviral DNA vector in combination with chloroquine, Human Gene Therapy 12, 3346–3363.
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: