Biologically active peptides and enzymatic approaches to their production

Enzyme and Microbial Technology

Volumn 18, Issue 3, 1996, Pages 162-183

  Gill, Iqbal ^a   López Fandiño, Rosina ^a   Jorba, Xavier ^a   Vulfson, Evgeny N ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Biotechnology; Continuous synthesis; Flavor peptides; Food derived peptides; New trends; Novel reaction systems; Peptide synthesis; Physiologically active peptides; Proteases; Recent developments; Strategies

Indexed keywords

FLAVORING AGENT; OLIGOPEPTIDE; PEPTIDE; PROTEINASE; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; HORMONE; IMMOBILIZED ENZYME; NEUROPEPTIDE; PEPTIDE FRAGMENT;

BIOTECHNOLOGY; CATALYST; ENZYME MECHANISM; FLAVOR; PEPTIDE SYNTHESIS; REVIEW; AMINO ACID SEQUENCE; METHODOLOGY; MOLECULAR GENETICS; SYNTHESIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; ANTIVIRAL AGENTS; BIOTECHNOLOGY; ENDOPEPTIDASES; ENZYMES, IMMOBILIZED; HORMONES; MOLECULAR SEQUENCE DATA; NEUROPEPTIDES; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PEPTIDES;

EID: 84874499889     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/0141-0229(95)00097-6     Document Type: Review

References (282)

1. Nishimura, T. and Kato, H. Taste of free amino acids and peptides. Food Rev. Int. 1988, 4, 175-194
2. Klein, L., Kaletta, C., Schnell, N., and Entian, K. D. Analysis of genes involved in biosynthesis of the lantibiotic subtilin. Appl. Environ. Microbiol. 1992, 58, 132-142
3. Barber, M., Elliot, G. J., Bordoli, R. S., Green, B. D., and Bycroft, B. W. Confirmation of the structure of nisin and its major degradation products by FAB-MS and FAB-MS/MS. Experientia 1988, 44, 266-270
4. Mørtvedt, C. I., Nissen-Meyer, J., Sletten, K., and Nes, I. F. Purification and amino acid sequence of Lactocin S, a bacteriocin produced by Lactobacillus sake L45. Appl. Environ. Microbiol. 1991, 57, 1829-1834
5. Nielsen, J. W., Dickson, J. S., and Crouse, J. D. Use of a bacteriocin produced by Pediococcus acidilacti to inhibit Listeria monocitogenes associated with fresh meat. Appl. Environ. Microbiol. 1990, 56, 2142-2145
6. Huges, J., Smith, T. W., Kosterlitz, H. W., Fothergill, L. A., Morgan, B. A., and Harris, H. R. Identification of two related pentapeptides from the brain with potent opiate antagonist activity. Nature 1975, 258, 577-579
7. Tachibana, S., Arai, K., Ohya, S., and Yoshida, S. Isolation and structure of dynorphin, an opioid peptide from porcine duodenum. Nature 1982, 295, 339-340
8. Goldstein, A., Fischli, W., Lowney, L. I., Hunkapiller, M., and Hood, L. Porcine pituitary dynorphin: Complete amino acid sequence of the biologically active heptadecapeptide. Proc. Natl. Acad. Sci. (U.S.A.) 1981, 78, 7219-7223
9. Rivier, J. E. and Brown, M. R. Bombesin, bombesin analogues, and related peptides: Effects on theromoregulation. Biochemistry 1978, 17, 1766-1771
10. Rizo, J. and Gierasch, L. M. Constrained peptides: Models of bioactive peptides and proteins substructures. Ann. Rev. Biochem. 1992, 61, 387-418
11. Tager, H. S. and Steiner, D. F. Peptide hormones. Ann. Rev. Biochem. 1974, 45, 510-538
12. Snyder, S. H. and Innis, R. B. Peptide neurotransmitters. Ann. Rev. Biochem. 1979, 48, 755-782
13. Anastasi, A., Erspamer, V., and Endean, R. Isolation and structure elucidation of cerulein, an active decapeptide from the skin of Hyla caerulea. Experientia 1967, 23, 699-700
14. Mutt, V. and Jorpes, J. E. Structure of porcine cholecystokinin-pancreozymin. Eur. J. Biochem. 1968, 6, 156-162
15. Meister, A. and Anderson, M. E. Glutathione. Ann. Rev. Biochem. 1983, 52, 711-760
16. Kleinkauf, H. and Von-Doehren, H. Peptide antibiotics, beta-lactams, and related compounds. Crit. Rev. Biotechnol. 1988, 8, 1-32
17. Antimicrobial Peptides Vol. 18b (Boman, H. G., Marsh, J., and Goode, J. A., Eds.). Ciba Foundation Symposium, Wiley, Chichester, 1994
18. Lewis, M. E., Khachaturian, H., and Walker, J. M. Endogenous opioids - Biological functions. Ann. Rev. Neurosci. 1984, 7, 223-255
19. Felix, A. M., Heimer, A. M., and Mowles, T. M. Growth hormone releasing factors. Ann. Rep. Med. Chem. 1985, 20, 185-192
20. Sporn, M. B. and Roberts, A. B. Peptide Growth Factors and Their Receptors. Springer Verlag, New York, 1991
21. Siddle, K. and Hutton, J. C. Peptide Hormone Action. Oxford University Press, Oxford, 1990
22. Peptides, Synthesis - Function (Rich, D. H. and Gross, E., Eds.). 7th Am. Peptide Symp. ESCOM Science, Netherlands, 1981
23. Peptides, Structure and Function (Hruby, V. J. and Rich, D. H., Eds.). Proc. 8th Am. Peptide Symp. ESCOM Science, Netherlands, 1983
24. Smith, J. A. and River, J. E. Peptides: Chemistry and Biology. Proc. 12th Am. Peptide Symp. ESCOM Science, Netherlands, 1992
25. Peptide Hormones (Berson, S. A. and Yalow, R. S., Eds.). North-Holland Publishing Co., New York, 1973
26. Aas, K. What makes an allergen an allergen. Allergy 1978, 33, 3-14
27. Handbook of Natural Toxins Vol. 1-7 (Tu, A. T., Ed.). Marcel Dekker, New York, 1983-1992.
28. Richardson, M. Protein inhibitors of enzymes. Food Chem. 1981, 6, 235-253
29. Stiles, M. E. and Hastings, J. W. Bacteriocin production by lactic acid bacteria: Potential for use in meat preservation. Trends Food Sci. Technol. 1991, 2, 247-251
30. Barnby-Smith, F. M. Bacteriocins: Applications in food preservation. Trends Food Sci. Technol. 1992, 3, 133-136
31. Meisel, H. and Schlimme, E. Milk proteins: Precursors of bioactive peptides. Trends Food Sci. Technol. 1990, 2, 41-43
32. Ariyoshi, Y. Angiotensin-converting enzyme inhibitors derived from food proteins. Trends Food Sci. Technol. 1993, 4, 139-144
33. Kohmura, M., Nio, N., and Ariyoshi, N. Inhibition of angiotensin converting enzyme by synthetic peptide fragments of human κ-casein. Agric. Biol. Chem. 1990, 54, 835-836
34. Kohama, Y., Oka, H., Kayamori, Y., Tsujikawa, K., Mimura, T., Nagase, Y. and Satake, M. Potent synthetic analogues of angiotensin-converting enzyme inhibitor derived from tuna muscle. Agric. Biol. Chem. 1991, 55, 2169-2170
35. Miyoshi, S., Ishikawa, H., Kaneko, T., Fukui, F., Tanaka, H., and Maruyama, S. Structures and activity of angiotensin-converting enzyme inhibitors in an α-zein hydrolysate. Agric. Biol. Chem. 1991, 55, 1313-1318
36. Meisel, H. and Frister, H. Chemical characterisation of bioactive peptides from in vivo digests of casein. J. Dairy Res. 1989, 56, 343-349
37. Mills, E. N. C., Alcocer, M. J. C., and Morgan, M. R. A. Biochemical interactions of food-derived peptides. Trends Food Sci. Technol. 1992, 3, 64-68
38. Baldo, B. A. Milk allergies. Aust. J. Dairy Res. 1984, 39, 120-128
39. Garcia-Olmedo, F., Salcedo, G., Sanchez-Monge, R., Gomez, L., Royo, J., and Carbonero, P. Plant proteinaceous inhibitors of proteinases and α-amylase. Oxford Surv. Mol. Cell Biol. 1987, 4, 275-334
40. Messina, M. and Messina, V. Increasing use of soyfoods and their potential role in cancer prevention. J. Am. Diet. Assoc. 1991, 91, 836-840
41. Kitts, D. D. and Yuan, Y. V. Caseinophosphopeptides and calcium bioavailability. Trends Food Sci. Technol. 1992, 3, 31-35
42. Saito, T., Yamaji, A., and Takatoshi, I. A new method of isolation of caseinoglycopeptide from sweet cheese whey. J. Dairy Sci. 1991, 74, 2831-2837
43. Biede, S. L. and Hammond, E. G. Swiss cheese flavor. II. Organoleptic analysis. J. Dairy Sci. 1979, 62, 238-248
44. McGugan, W. A., Emmons, D. B., and Larmond, E. Influence of volatile and nonvolatile fractions on intensity of Cheddar cheese flavor. J. Dairy Sci. 1979, 62, 398-403
45. Cliffe, A. J. and Law, B. A. A time-course study of peptide production in accelerated ripened cheese. Food Biotechnol. 1991, 5, 1-17
46. Nishimura, T., Rhue, M. R., Okitani, A., and Kato, H. Components contributing to the improvement of meat taste during storage. Agric. Biol. Chem. 1988, 52, 2323-2330
47. Sturtevant, F. M. Aspartame - New food ingredient - Reply. J. Environ. Sci. Health Part A Environ. Sci. Eng. 1985, 20, 863-901
48. Grenby, T. H. Intense sweetners for the food industry: An overview. Trends Food Sci. Technol. 1991, 2, 2-6
49. Nosho, Y., Seki, T., Kondo, M., Ohfuji, T., Tamura, M., and Okai, H. Molecular design of inverted aspartame type sweetners. J. Agric. Biol. Chem., 1990, 38, 1368-1373
50. Ota, M., Nio, N., and Ariyoshi, Y. Enzymatic synthesis and chemical properties of sweet aminomalonyl (Ama) dipeptide esters (R)-Ama-(S)-PheOMe and (R)-Ama-(S)-PheOEt. Biosci. Biotechnol. Biochem. 1993, 57, 808-813
51. Arai, S. A. The bitter flavour due to peptides or protein hydrolysates and its control by bitterness masking with acidic oligopeptides. In: ACS: Undesirable Flavours Symposium (Charlambous, G., Ed.) American Chemical Society, Washington, 1980, 133-137
52. Matoba, T., Hayashi, R., and Hata, T. Isolation of bitter peptides from a tryptic hydrolysate of casein and their chemical structure. Agric. Biol. Chem. 1970, 34, 1235-1243
53. Mojarro-Guerra, S. H., Amado, R., Arrigoni, E., and Solms, J. Isolation of low-molecular weight taste peptides from Vacherin Mont d'Or cheese. J. Food Sci. 1991, 56, 943-947
54. Kirimura, J., Shimizu, A., Kimizura, A., Ninomiya, T., and Katsuya, J. The contribution of amino acids and peptides to the taste of foodstuffs. J. Agric. Food Chem. 1969, 17, 689-695
55. Ohyama, S., Ishibashi, N., Tamura, M., Nishizaki, H., and Okai, H. Synthesis of bitter peptides composed of aspartic acid and glutamic acid. Agric. Biol. Chem. 1988, 52, 871-872
56. Tada, M., Shinoda, I., and Okai, H. L-ornithyltaurine, a new salty peptide. J. Agric. Food Chem. 1984, 32, 992-996
57. Kawasaki, Y., Seki, T., Tamura, M., Kikuchi, E., Tada, M., and Okai, H. Glycine methyl or ethyl ester hydrochloride as the simplest examples of salty peptides and their derivatives. Agric. Biol. Chem. 1988, 52, 2679-2681
58. Aso, K. Enzymatic approach to the synthesis of a lysine-containing sweet peptide, N-acetyl-L-phenylalanyl-L-lysine. Agric. Biol. Chem. 1989, 53, 729-733
59. Kurihara, Y. and Nirasawa, S. Sweet, antisweet, and sweetness-inducing substances. Trends Food Sci. Technol. 1994, 5, 37-42
60. Ishibashi, N., Arita, Y., Kanehisa, H., Kouge, K., Okai, H., and Fukui, S. Bitterness of leucine containing peptides. Agric. Biol. Chem. 1987a, 51, 2389-2394
61. Ishibashi, N., Sadamori, K., Yamamoto, O., Kanehisa, H., Kouge, K., Kikuchi, E., Okai, H., and Fukui, S. Bitterness of phenylalanine- and tyrosine-containing peptides. Agric. Biol. Chem. 1987b, 51, 3309-3313
62. Ishibashi, N., Ono, I., Kato, K., Shigenaga, T., Shinoda, I., Okai, H., and Fukui, S. Role of the hydrophobic amino acid residue in the bitterness of peptides. Agric. Biol. Chem. 1988a, 52, 91-94
63. Otagiri, K., Nosho, Y., Shinoda, I., Fukui, H., and Okai, H. Studies on a model of bitter peptides including arginine, proline and phenylalanine residues. I. Bitter taste of di- and tri-peptides and bitterness increase of the model peptides by extension of the peptide chain. Agric. Biol. Chem. 1985, 49, 1019-1026
64. Nosho, Y., Otagiri, K., Shinoda, I., and Okai, H. Studies on a model of bitter peptides including arginine, proline and phenylalanine residues. II. Bitterness behavior of a tetrapeptide (Arg-Pro-Phe-Phe) and its derivatives. Agric. Biol. Chem. 1985, 49, 1829-1839
65. Ishibashi, I., Kubo, T., Chino, M., Fukui, H., Shinoda, I., Kikuchi, E., Okai, H., and Fukui, S. Taste of proline containing peptides. Agric. Biol. Chem. 1988b, 52, 95-98
66. Yamasaki, Y. and Maekawa, K. A peptide with delicious taste. Agric. Biol. Chem. 1978, 42, 1761-1765
67. Tamura, M., Nakatsuka, T., Tada, M., Kawasaki, Y., Kikuchi, E., and Okai, H. The relationship between taste and primary structure of "Delicious Peptide" (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from beef soup. Agric. Biol. Chem. 1988, 53, 319-325
68. Seki, T., Kawasaki, Y., Tamura, M., Tada, M., and Okai, H. Further study on the salty peptide ornithyl-β-alanine. Some effects of pH and additive ions on the saltiness. J. Agric. Food Chem. 1990, 38, 25-29
69. Carson, J. F. Chemical and biological properties of onions and garlic. Food Rev. Int. 1987, 3, 71-103
70. Lancaster, J. E. and Shaw, M. L. Gamma-glutamyl peptides in the biosynthesis of s-alkenyl-L-cysteine sulphoxides (flavour precursors) in Allium. Phytochemistry 1989, 28, 455-460
71. Oh, Y.-C., Shu, C.-K., and Ho, C.-T. Formation of novel 2(1H)-pyrazinones as peptide-specific Maillard reaction products. J. Agric. Food Chem. 1992a, 40, 118-121
72. Oh, Y.-C., Hartman, T. G., and Ho, C.-T. Volatile compounds generated from the Maillard reaction of Pro-Gly, Gly-Pro, and a mixture of glycine and proline with glucose. J. Agric. Food Chem. 1992b, 40, 1878-1880
73. Pokorny, J. Natural antioxidants for food use. Trends Food Sci. Technol. 1991, 2, 223-227
74. Chan, K. M., Decker, E. A., and Means, W. J. Extraction and activity of carnosine, a naturally occurring antioxidant in beef muscle. J. Food Sci. 1993, 58, 1-4
75. Iyengar, R. and McEvily, A. J. Anti-browning agents: Alternatives to the use of sulfites in foods. Trends Food Sci. Technol. 1992, 3, 60-64
76. Oszmianski, J. and Lee, C. Y. Inhibition of polyphenol oxidase activity and browning by honey. J. Agric. Food Chem. 1990, 38, 1892-1895
77. Kato, A., Shimokawa, K., and Kobayashi, K. Improvement of the functional properties of insoluble gluten by pronase digestion followed by dextran conjugation. J. Agric. Food Chem. 1991, 39, 1053-1056
78. Shimizu, M., Lee, S. W., Kaminogawa, S., and Yamauchi, K. Emulsifying properties of an N-terminal peptide obtained from the peptide hydrolysate of αS1-casein. J. Food Sci. 1984, 49, 1117-1120
79. Shimizu, M., Lee, S. W., Kaminogawa, S., and Yamauchi, K. Functional properties of a peptide of 23 residues purified from the peptide hydrolysate of αS1-casein: Changes in the emulsifying activity during purification of the peptide. J. Food Sci. 1986, 51, 1248-1252
80. Lee, S. W., Shimizu, M., Kaminogawa, S., and Yamauchi, K. Emulsifying properties of peptides obtained from the hydrolysates of beta-casein. Agric. Biol. Chem. 1987, 51, 161-166
81. Ochiai, K., Kamata, Y., and Shibasaki, K. Effect of tryptic digestion on emulsifying properties of soy protein. Agric. Biol. Chem. 1982, 46, 91-96
82. Chobert, J.-M., Sitohy, M. Z., and Whitaker, J. R. Solubility and emulsifying properties of caseins modified enzymatically by Staphylococcus aureus V8 protease. J. Agric. Food Chem. 1988a, 36, 220-224
83. Chobert, J.-M., Bertrand-Harb, C., and Nicolas, M.-G. Solubility and emulsifying properties of caseins and whey proteins modified enzymatically by trypsin. J. Agric. Food Chem. 1988b, 36, 883-892
84. Turgeon, S. L., Gauthier, S. F., and Paquin, P. Interfacial and emulsifying properties of whey peptide fractions obtained with a two-step ultrafiltration process. J. Agric. Food Chem. 1991, 39, 673-676
85. Dale, C. J. Raw materials and beer quality. Brewer 1986, 72, 468-470
86. Siemensma, A. D., Weijer, W. J., and Bak, H. J. The importance of peptide lengths in hypoallergenic infant formulae. Trends Food Sci. Technol. 1993, 4, 16-21
87. Aso, K., Kodaka, H., Fukushi, H., and Lee, H. H. Trypsin catalysed synthesis of arginylarginine dipeptide from L-arginine ethyl ester. Biotechnol. Lett. 1992, 14, 451-456
88. Hajos, G., Noetzold, H., Halasz, A., and Ludwig, E. Characterisation of peptides enriched in methionine by enzymatic peptide modification. Acta Aliment. Acad. Sci. Hung. 1990, 19, 73-78
89. Friedman, M. and Finot, P.-A. Nutritional improvement of bread with lysine and γ-glutamyl-lysine. J. Agric. Food Chem. 1990, 38, 2011-2020
90. Lopez-Bajonero, L. J., Lara-Calderon, P., Galvez-Mariscal, A., Velazques-Arellano, A., and Lopez-Munguia, A. Enzymatic production of a low-phenylalanine product from skim milk powder and caseinate. J Food Sci. 1991, 56, 938-942
91. Nakamura, T., Syukunobe, Y., Sakurai, T., and Idota, T. Enzymatic production of hypoallergenic peptides from casein. Milchwissenschaft. 1993, 48, 11-14
92. Maubois, J. L. and Leonil, J. Peptides du lait a activite biologique. Lait 1989, 69, 245-269
93. Maubois, J. L., Léonil, J., Trouvé, R., and Bouhallab, S. Les peptides du lait a activite physiologique. III. Peptides du lait á effect cardiovasculaire: Activitiés antithrombotique et antihypertensive. Lait 1991, 71, 249-255
94. Addeo, F., Chianese, L., Salzano, A., Sacchi, R., Cappuccio, U., Ferranti, P., and Malorni, A. Characterization of the 12% trichloroacetic acid-insoluble oligopeptides of Parmigiano-Reggiano cheese. J. Dairy Res. 1992, 59, 401-411
95. Peptides: Synthesis-Structure-Function (Rich, D. H. and Gross, E., Eds.). Pierce Chemical Co., Rockford-Illinois, 1981
96. Peptides (Penke, B. and Török, A., Eds.). Walter de Gruyter, Berlin, 1988
97. Atherton, E. and Sheppard R. C. Solid Phase Peptide Synthesis. A Practical Approach. IRL Press, Oxford, 1989
98. Aasmul-Olsen, S., Anderson, A. J., Thorbek, P., and Widmer, F. The technology of peptide synthesis. In: Eighth International Conference on Tetanus. (Nistico, G., Bizzini, B., Bytchenko, B. and Triau, R., Eds.) Pythagora Press, Rome-Milan, 1989, 191-208
99. Andersen, A. J., Fomsgaard, J., and Aasmul-Olsen, S. Current enzymatic possibilities in the technology of peptide synthesis: Methods of synthesis and practical examples. Chimicaoggi 1991, 3, 17-25
100. Andersen, A. J., Fomsgaard, J., and Aasmul-Olsen, S. Current enzymatic possibilities in the technology of peptide synthesis: Process development in enzymatic peptide synthesis. Chimicaoggi 1991, 4, 17-23
101. Bodzansky, M. Peptide Chemistry. Springer Verlag, New York, 1993
102. Bongors, J. and Heimer, E. P. Recent applications of enzymatic peptide synthesis. Peptides 1994, 15, 183-193
103. Harford, S. Genetic engineering and the pharmaceutical industry. In: Molecular Biology and Biotechnology (Walker, J. M. and Gingold, E. B., Eds.). Royal Society of Chemistry, London, 1988, 149-158
104. Jakubke, H.-D. Enzymatic peptide synthesis. In: The Peptides Vol. 9. (Udenfriend, S. and Meienhofer, J., Eds.). Academic Press, San Diego, 1987, 103-143
105. Kullmann, W. Enzymatic Peptide Synthesis. CRC Press, Boca Raton, 1987
106. The Peptides. Analysis, Synthesis and Biology Vol. 2. (Udenfriend, S. and Meienhofer, J., Eds.). Academic Press, New York, 1980
107. The Peptides. Analysis, Synthesis and Biology Vol. 9. (Udenfriend, S. and Meienhofer, J., Eds.). Academic Press, New York, 1987
108. Wetzel, R. and Goeddel, D. V. Synthesis of polypeptides by recombinant DNA methods. In: The Peptides. Analysis, Synthesis and Biology Vol. 5. (Udenfriend, S. and Meienhofer, J., Eds.). Academic Press, New York, 2-65
109. Stewart, J. H. and Young, J. D. Solid Phase Peptide Synthesis. Pierce Chemical Co., Rockford, Illinois, 1984
110. Merrifield, R. B. Solid phase peptides synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154
111. Valembois, C., Mendre, C., Cavadore, J. C., and Calas, B. Continuous flow synthesis of a biologically active small protein and a large peptide. Tetrahedron Lett. 1992, 33, 4005-4008
112. Bashkin, J. K., McBeath, R. J., Modak, A. S., Sample, K. R., Wise, W. B. Synthesis and characterization of oligonucleotide peptides. J. Org. Chem. 1991, 56, 3168-3176
113. De Bont, D. B. A., Moree, W. J., Van Boom, J. H., and Liskamp, R. M. J. Solid-phase synthesis of o-phosphorothioyl-serine- and -threonine-containing peptides as well as of o-phosphoserine- and -threonine-containing peptides. J. Org. Chem. 1993, 58, 1309-1317
114. Peters, S., Bielfeldt, T., Meldal, M., Bock, K., and Paulsen, H. Multiple-column solid-phase glycopeptide synthesis. J. Chem. Soc. Perkin. Trans. 1992, 6, 1163-1169
115. Rabanal, F., Haro, I., Reig, F., and García-Antón, J. M. Solid phase synthesis of potential antigenic peptides and new lipopeptides of Hepatitis B virus. J. Chem. Soc. Perkin. Trans. 1991, 1, 945-952
116. Cohen-Anisfield, S. T. and Lansbury, P. T. A practical, convergent method for glycopeptide synthesis. J. Am. Chem. Soc. 1993, 115, 10531-10537
117. Kasche, V. Proteases in peptide synthesis. In: Proteolytic Enzymes: A Practical Approach. (Benyon, R. J. and Bond, J. S., Eds.). IRL Press, Oxford, 1989, 125-143
118. Vandekerckhove, J., Van Damme, J., Lijsebettens, M. V., Botterman, J., De Block, M., Vandewiele, M., De Clercq, A., Leemans, J., Montagu, M. V., and Krebbers, E. Enkephalins produced in transgenic plants using modified 2S seed storage proteins. Biotechnology 1989, 7, 929-932
119. Schellenberger, V. Specificity of protease-catalysed acyl transfer reactions. Biol. Chem. Hoppe-Seyler 1991, 372, 743-750
120. Doel, M. T., Eaton, M., Cook, E. A., Lewis, H., Patel, T., and Carey, N. H. The expression in E. coli of synthetic repeating polymeric genes coding for poly(L-aspartyl-L-phenylalanine). J. Nucleic Acids Res. 1980, 8, 4575-4592
121. Murata, T., Horinouchi, S., and Beppu, T. Production of poly(L-aspartyl-L-phenylalanine) in E. coli. J. Biotechnol. 1993, 28, 301-312
122. Oyama, K. Enzymatic synthesis of aspartame in organic solvents. In: Biocatalysis in Organic Media (Laane, C., Tramper, J., and Lilly, M. D., Eds.). Elsevier, Amsterdam, 1987, 209-224
123. Merkler, D. J. C-terminal amidated peptides: Production by the in vitro enzymatic amidation of glycine-extended peptides and the importance of the amide to bioactivity. Enzyme Microb. Technol. 1994, 16, 450-456
124. Davies, H. G., Green, R. H., Kelly, D. R., and Roberts, S. M. Recent advances in the generation of chiral intermediates using enzymes. CRC Crit. Rev. Biotechnol. 1990, 10, 129-153
125. Faber, K., Franssen, M. C. R. Prospects for the increased application of biocatalysis in organic transformations. Trends Biotechnol. 1993, 11, 461-469
126. Jones, J. B. Enzymes in organic synthesis. Tetrahedron 1986, 42, 3351-3403
127. Klibanov, A. M. Assymetric transformations catalysed by enzymes in organic solvents. Acc. Chem. Res. 1990, 23, 114-120
128. Margolin, A. L. Enzymes in the synthesis of chiral drugs. Enzyme Microb. Technol. 1993, 15, 266-280
129. Roberts, S. M. and Turner, N. J. Some recent developments in the use of enzyme catalysed reactions in organic synthesis. J. Biotechnol. 1992, 22, 227-244
130. Sih, C. J. and Wu, S. H. Resolution of enantiomers via biocatalysis. Top. Stereochem. 1989, 19, 63-89
131. Vulfson, E. N. Enzymatic synthesis of food ingredients in low-water media. Trends Food Sci. Technol. 1993, 4, 209-215
132. Wong, C.-H. Enzymatic catalysts in organic synthesis. Science 1989, 244, 1145-1152
133. Wong, C.-H. and Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series, Vol. 12. Pergamon, Oxford, 1994
134. Spirin, A. S., Baranov, V. I., Ryabova, L. A., Ovodov, S. Y., and Alakhov, Y. B. A continuous cell-free translation system capable of producing polypeptides in high yield. Science 1988, 242, 1162-1164
135. Endo, Y., Otsuzuki, S., Ito, K., and Miura, K.-I. Production of an enzymatic active protein using a continuous flow cell-free translation system. J. Biotechnol. 1992, 25, 221-230
136. Nakano, H., Tanaka, T., Kawarasaki, Y., and Yamane, T. An increased rate of cell-free protein synthesis by condensing wheatgerm extract with ultrafiltration membranes. Biosci. Biotechnol. Biochem. 1994, 58, 631-634
137. Noren, C. J., Anthony-Cahill, S. J., Griffith, M. C., and Schultz, P. G. A general method for site-specific incorporation of unnatural amino acids into proteins. Science 1989, 244, 182-189
138. Fersht, A. R. Dissection of the structure and activity of the tyrosyl-tRNA synthetase by site-directed mutagenesis. Biochemistry 1987, 26, 8031-8037
139. Kleinkauf, H. and Von Dohren, H. Biosynthesis of peptide antibiotics. Ann. Rev. Microbiol. 1987, 41, 259-272
140. Nakajima, H., Kitabatake, S., Tsurutani, R., Yamamoto, K., Tomioka, I., and Imahori, K. Int. J. Peptide Protein Res. 1986, 28, 179-185
141. Proceedings of First International Workshop on Enzymes in Peptide Synthesis (Bielke, H. and Scheler, W. Eds.). Biomed. Biophys. Acta 1991, 50, S1-S270
142. Chaiken, I. M., Komoriya, A., Ohno, M., and Widmer, F. Use of enzymes in peptide synthesis. Appl. Biochem. Biotechnol. 1982, 7, 385-399
143. Glass, J. D. Enzymes as reagents in the synthesis of peptides. Enzyme Microb. Technol. 1981, 3, 2-7
144. Jakubke, H.-D., Kuhl, P., and Konnecke, A. Basic principles of protease catalysed peptide bond formation. Angew. Chem. Int. Ed. Engl. 1985, 24, 85-93
145. Morihara, K. Using proteases in peptide synthesis. Trends Biotechnol. 1987, 5, 164-170
146. Sinisterra, J. V. and Alcántara, A. R. Synthesis of peptides catalyzed by enzymes. A practical overview. J. Mol. Catal. 1993, 84, 327-364
147. Van't Hoff, J. H. Uber die zunehmende Dedeutung der anorganischen Chemie. Z. Anor. Allg. Chem. 1988, 18, 1-13
148. Bergmann, M., Zervas, L., and Fruton, J. S. On proteolytic enzymes. VI. On the specificity of papain. J. Biol. Chem. 1935. 111, 225-244
149. Bergmann, M. and Fruton, J. S. On proteolytic enzymes. XIII. Synthetic substrates for chymotrypsin. J. Biol. Chem. 1937, 118, 405-415
150. Bergmann, M. and Fraenkel-Conrat, H. The enzymatic synthesis of peptide bonds. J. Biol. Chem. 1938, 124, 1-6
151. Bergmann, M. and Fruton, J. S. Some synthetic and hydrolytic experiments with chymotrypsin. J. Biol. Chem. 1938, 124, 321-329
152. Isowa, Y., Ohmori, M., Ichikawa, T., Kurita, H., Saito, M., and Mori, K. Synthesis of peptides by means of proteolytic enzymes. Bull. Chem. Soc. Jpn. 1977, 50, 2762-2765
153. Isowa, Y., and Ichikawa, T. Synthesis of N-acyl-dipeptide derivatives by metalloproteinases. Bull. Chem. Soc. Jpn. 1979, 52, 796-800
154. Kullmann, W. Enzymatic synthesis of Leu- and Met-enkephalin. Biochem. Biophys. Res. Commun. 1979, 91, 693-698
155. Morihara, K. and Oka, T. α-Chymotrypsin as the catalyst for peptide synthesis. Biochem. J. 1978, 41, 179
156. Chaiken, I. M., Komoriya, A., Ohno, M., and Widmer, F. Use of enzymes in peptide synthesis. Appl. Biochem. Biotechnol. 1982, 7, 385-399
157. Fruton, J. S. Proteinase catalysed synthesis of peptide bonds. Adv. Enzymol. Relat. Areas Mol. Biol. 1982, 53, 239-306
158. Kuhl, P., Döring, G., Neubert, K., Jakubke, H.-D. Synthese von N-geschütztem Eledoisin (6-11)-Hexapeptid unter Verwendug von Proteasen als Biokatalysatoren. Monatsch. Chem. 1984, 115, 423-430
159. Kullmann, W. Protease catalysed peptide bond formation: Application to synthesis of the COOH-terminal octapeptide fragment of cholecystokinin. Proc. Natl. Acad. Sci. (U.S.A.) 1982, 79, 2840-2844
160. Kullmann, W. Enzymatic synthesis of dynorphin (1-8). J. Org. Chem. 1983, 47, 5300-5303
161. Kullmann, W. Protease catalysed synthesis of melanocyte stimulating hormone (MSH) fragments. J. Prot. Chem. 1983, 2, 289-301
162. Oyama, K., Niishimura, S., Nonaka, Y., Kihara, K., and Hashimoto, T. Synthesis of aspartame precursor by immobilized thermolysin. J. Org. Chem. 1981, 46, 5241-5242
163. Stoineva, I. B. and Petkov, D. D. Chemo-enzymatic incorporation of D-amino acids into peptides. FEBS Lett. 1985, 183, 103-106
164. Takai, H., Sakato, K., Nakamizo, N., and Isowa, Y. Enzymatic synthesis of caerulein peptide. In: Peptide Chemistry 1980, Protein Research Foundation, Osaka, 1981, 213-214
165. Widmer, F., Bayne, S., Houen, G., Rigby, R. D., Whittaker, R. G., and Johansen, J. T. Use of proteolytic enzymes for the synthesis of fragments of mouse epidermal growth factor. In: Peptides 1984 (Ragnurrson, U., Ed.). Almquist, Stockholm, 1985, 193-196
166. Cheetham, P. S. J. Case studies in applied biocatalysis - from ideas to products. In: Applied Biocatalysis (Cabral, J. M. S., Best, D., Boros, L., and Tramper, J., Eds.). Harwood Academic, Chur, Switzerland 1994, 47-109
167. Kimura, Y., Muraya, K., Araki, Y., Matsuoka, H., Nakanishi, K., and Matsuno, R. Synthesis of peptides consisting of essential amino acids by a three reactor system using three proteinases and an organic solvent. Agric. Biol. Chem. 1990b, 54, 3331-3333
168. Clapés, P., Valencia, G., Reig, F., and Garcia-Anton, J. M. Kinetically controlled enzyme catalysed synthesis of kyotorphin. Appl. Biochem. Biotechnol. 1987, 15, 89-96
169. Aso, K. Enzymatic approach to the synthesis of a lysine-containing sweet peptide, N-acetyl-L-phenylalanyl-L-lysine. Agric. Biol. Chem. 1989, 53, 729-733
170. Bille, V., Ripak, C., Van Aasche, I., Forni, L., Degelaen, L., and Scarso, A. Semi-enzymatic synthesis of somatostatin. In: Proceedings of 21st European Peptide Symposium (Giralt, E. and Andreu, D., Eds.). ESCOM, Leiden, the Netherlands 1991, 253-254
171. Xaus, N., Albericio, F., Jorba, X., Calvet, S., Clapés. P., Torres, J. L., and Valencia, G. Racemization free coupling of peptide segments. Synthesis of an insect neuropeptide. Int. J. Peptide Protein Res. 1992, 39, 528-532
172. Hwang, B. K., Gu, Q.-M., and Sih, C. J. Enzyme-catalyzed peptide segment condensation using 5(4H)-oxazolones as acyl donors. J. Am. Chem. Soc. 1993, 115, 7912-7913
173. Homandberg, G. A. and Laskowski, M. Enzymatic resynthesis of the hydrolized peptide bond(s) in ribonuclease-S. Biochemistry 1979, 18, 586
174. Komoriya, A., Homandberg, G. A., and Chaiken, I. M. Enzyme catalysed formation of semisynthetic staphylococcal nuclease using a synthetic fragment (8-glycine)-synthetic-(6-49). Int. J. Peptide Protein Res. 1980, 16, 433-440
175. Juillerat, M. and Homandberg, G. A. Clostripain catalysed reformulation of a peptide bond in a cytochrome-C fragment complex. Int. J. Peptide Protein Res. 1981, 18, 335-342
176. Graf, L. and Li, C. H. Human somatotropin: Covalent reconstitution of two polypeptide contiguous fragments with thrombin. Proc. Natl. Acad. Sci. (U.S.A.) 1981, 78, 6135-6138
177. Chu, S.-C., Wang, C. C., and Brandenburg, D. Intramolecular enzymatic peptide synthesis: Trypsin mediated coupling of the peptide bond between B22-arginine and B23-glycine in a split crosslinked insulin. Hoppe Seylers Z. Physiol. Chem. 1981, 362, 647-654
178. Jackson, D. Y., Burnier, J., Quan, C., Stanley, M., Tom, J., and Wells, J. A. A designed peptide ligase for total synthesis of ribonuclease A with unnatural catalytic residues. Science 1994, 266, 243-247
179. Morihara, K., Oka, T., Tsuzuki, H., Tochino, Y., and Kanaya, T. Achromobacter protease I catalysed conversion of porcine insulin into human insulin. Biochem. Biophys. Res. Commun. 1980, 92, 396-402
180. 2(142α)Hb. J. Biol. Chem. 1982, 257, 1622-1625
181. Breddam, K., Widmer, F., and Meldal, M. Amidation of growth hormone releasing factor (1-29) by serine carboxypeptidase catalysed transpeptidation. Int. J. Peptide Protein. Res. 1991, 37, 153-160
182. Carrea, G. Biocatalysis in water-organic solvent 2-phase systems. Trends Biotechnol. 1984, 2, 102-106
183. Halling, P. J. Solvent selection for biocatalysis in mainly organic systems: Prediction of effects on equilibrium position. Biotechnol. Bioeng. 1990, 35, 691-701
184. Wong, C.-H., Matos, J. R., West, J. B., and Barbas, C. F. Practical enzymatic approaches to unusual peptides. J. Ind. Microbiol. 1988, 29, suppl. 3, 171-177
185. Schuster, M., Aaviksaar, A., Haga, M., Ullmann, U., and Jakubke, H.-D. Protease-catalysed peptide synthesis in frozen aqueous systems: The freeze-concentration model. Biomed. Biochim. Acta 1991, 50, 84
186. Brink, L. E. S., Tramper, J., Luyben, K. C. A. M., and Vant Riet, K. Biocatalysis in organic media. Enzyme Microb. Technol. 1988, 10, 736-744
187. Dordick, J. S. Enzymatic catalysis in monophasic organic solvents. Enzyme Microb. Technol. 1989, 11, 194-211
188. Khemelnitsky, Y. L., Levashov, A. V., Klyachko, N. E., and Martinek, K. Engineering biocatalytic systems in organic media with low water content. Enzyme Microb. Technol. 1988, 10, 710-724
189. Klibanov, A. M. Enzymatic catalysis in anhydrous organic solvents. Trends Biochem. Sci. 1989, 14, 141-144
190. Klibanov, A. M. Asymmetric transformations catalysed by enzymes in organic solvents. Acc. Chem. Res. 1990, 23, 114-120
191. Zaks, A. and Klibanov, A. M. Enzymatic catalysis in non-aqueous solvents. J. Biol. Chem. 1988, 263, 3194
192. Zaks, A. and Russell, A. J. Enzymes in organic solvents: Properties and applications. J. Biotechnol. 1988, 8, 259-270
193. Deetz, J. S. and Rozzell, J. D. Enzyme catalysed reactions in non-aqueous media. Trends Biotechnol. 1988, 6, 15-19
194. Schwarz, A., Steinke, D., Kula, M.-R., and Wandrey, C. Optimization of enzyme mediated peptide bond formation. Biotechnol. Appl. Biochem. 1990, 12, 188-195
195. Fitzpatrick, P. A., Ringe, D., and Klibanov, A. M. Computer assisted modelling of subtilisin enantioselectivity in organic solvents. Biotechnol. Bioeng. 1992, 40, 735-742
196. Sakurai, T., Margolin, A. L., Russell, A. J., and Klibanov, A. M. Control of enzyme enantioselectivity by the reaction medium. J. Am. Chem. Soc. 1988, 110, 7236-7237
197. Tawaki, S. and Klibanov, A. M. Inversion of enzyme enantiose-lectivity mediated by the solvent. J. Am. Chem. Soc. 1992, 114, 1882-1884
198. Terradas, F., Teston-Henry, M., Fitzpatrick, P. A., and Klibanov, A. M. Marked dependence of enzyme prochiral selectivity on the solvent. J. Am. Chem. Soc. 1993, 115, 390-396
199. Vulfson, E. N., Ahmed, G., Gill, I., Kozlov, I. A., Goodenough, P. A., and Law, B. A. L-DOPA ester synthesis by α-chymotrypsin in organic solvents. Biotechnol. Lett. 1990, 12, 597-602
200. Adlercreutz, P. and Matiasson, B. Aspects of biocatalyst stability in organic solvents. Biocatalysis 1987, 1, 108-118
201. Zaks, A. and Klibanov, A. M. Enzyme catalysts in organic media at 100°C. Science 1984, 224, 1249-1251
202. Barbas, C. F. and Wong, C.-H. Papain catalysed peptide synthesis: Control of amidase activity and the introduction of unusual amino acids. J. Chem. Soc. Chem. Commun. 1987, 533-534
203. Cerovsky, V. and Martinek, K. Peptide synthesis catalysed by native proteinase K in water miscible organic solvents with low water content. Collect. Czech. Chem. Commun. 1989, 54, 2027-2041
204. Chen, S. T., Hsiao, S.-C., and Wang, K.-T. Stable industrial protease catalysed peptide bond formation in organic solvents. Org. Med. Chem. Lett. 1991, 9, 445-450
205. Clapés, P., Adlercreutz, P., and Mattiasson, B. Enzymatic peptide synthesis in organic media: Nucleophile specificity and medium engineering in α-chymotrypsin catalysed reactions. Biotechnol. Appl. Biochem. 1990, 12, 376-386
206. Clapés, P., Adlercreutz, P., and Mattiasson, B. Enzymatic peptide synthesis in organic media: A comparative study of water miscible and water immiscible systems. J. Biotechnol. 1990, 15, 323-338
207. Fischer, U., Zeitschel, U., and Jakubke, H.-D. α-Chymotrypsin catalysed peptide synthesis in an acetonitrile-water system: Studies on the efficiency of nucleophiles. Biomed. Biochim. Acta. 1991, 50, 139-143
208. Fulcrand, V., Jacquier, R., Lazaro, R., and Viallefont, P. New biocatalysts for peptide synthesis: Gels of copolymerised acrylic-acid derivatives of α-chymotrypsin and polyoxyethylene. Tetrahedron Lett. 1990, 46, 3909-3920
209. Fulcrand, V., Jacquier, R., Lazaro, R., and Viallefont, P. Enzymatic
210. Gaertner, H., Watanabe, T., Sinisterra, J. V., and Puigserver, A. Peptide synthesis catalysed by modified α-chymotrypsin in low water media. J. Org. Chem. 1991, 56, 3149-3153
211. Kise, H., Hayakawa, A., and Noritomi, H. Chitin-α-chymotrypsin complex as a catalyst for amino acid esterification and peptide synthesis in organic solvents. Biotechnol. Lett. 1987, 9, 543-548
212. Kise, H., Hayakawa, A., and Noritomi, H. Protease catalysed synthetic reactions and immobilization-activation of the enzymes in hydrophilic organic solvents. J. Biotechnol. 1990, 14, 239-254
213. Kise, H. and Hayakawa, A. Immobilization of proteases to porous chitosan beads and their catalysis for ester and peptide synthesis in organic solvents. Enzyme Microb. Technol. 1991, 13, 584-588
214. Kuhl, P., Hailing, P. J., and Jakubke, H.-D. α-chymotrypsin suspended in organic solvents with salt hydrates is a good catalyst for peptide synthesis from mainly undissolved reactants. Tetrahedron Lett. 1990, 31, 5213-5216
215. Noritomi, H. and Kise, H. Peptide synthesis by α-chymotrypsin immobilized with PVA in ethanol. Biotechnol. Lett. 1987, 9, 383-386
216. Reslow, M., Adlercreutz, P., and Mattiasson, B. Influence of water on protease catalysed peptide synthesis in acetonitrile-water mixtures. Eur. J. Biochem. 1988, 177, 313-318
217. Ricca, J. M. and Crout, D. H. G. Peptide synthesis catalysed by α-chymotrypsin in organic solvents. J. Chem. Soc. Perkin Trans. 1989, 3, 2126
218. Slomczynska, U. and Leplawy, T. Peptide synthesis catalysed by α-chymotrypsin in ultra low water media. In: Peptides 1988 (Jung, G. and Bayer, E., Eds.). Walter de Gruyter, Berlin, 1989, 253-255
219. Callstrom, M. R., Hill, T. G., Wartchow, C. A., Huston, M. E., Bednarski, M. D., Oehler, L. M., and Wang, P. The synthesis of new carbohydrate-based materials and their use for the stabilization of proteins. In: Harnessing Biotechnology for the 21st Century (Landisch, M. R. and Bose, A., Eds.). American Chemical Society, Washington, 1992, 63
220. Kitaguchi, H. and Klibanov, A. M. Enzymatic peptide synthesis via segment condensation in the presence of water mimics. J. Am. Chem. Soc. 1989, 111, 9272-9273
221. Mitin, Y. V. Peptide synthesis catalysed by papain in organic solvents containing minimum water. In: Peptides 1988 (Jung, G. and Bayer, E., Eds.). Walter de Gruyter, Berlin, 1989, 250-253
222. Kimura, Y., Yoshida, T., Muraya, K., Nakanishi, K., and Matsuno, R. Continuous synthesis of a tripeptide by successive condensation and transesterification catalysed by two immobilized proteases in organic solvent. Agric. Biol. Chem. 1990a, 54, 1433-1440
223. Nakanishi, K., Kamikubo, T., and Matsuno, R. Continuous synthesis of N-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester with an immobilized thermolysin in an organic solvent. Biotechnology 1985, 3, 459-464
224. Nakanishi, K., Takeuchi, A., and Matsuno, R. Long term continuous synthesis of aspartame precursor in a column reactor with an immobilized thermolysin. Appl. Microbiol. Biotechnol. 1990, 32, 633-636
225. Auriol, D., Paul, F., and Monsan, P. A new peptidase enzyme useful for peptide and amino acid derivative synthesis by reverse hydrolysis reactions. Ann. N.Y. Acad. Sci. 1990, 613, 201-206
226. Butler, L. G. Enzymes in non-aqueous solvents. Enzyme Microb. Technol. 1979, 1, 253-259
227. Belova, A. B., Mozhaev, V. V., Levashov, A. V., Shergeeva, M. V., Martinek, K., and Khmelnitsky, Y. L. Relationship between the physiochemical characteristics of organic solvents and their denaturing capacity towards proteins. Biokhimiya 1992, 56, 1357-1373
228. Laane, C., Boeren, S., Vos, K., and Veeger, C. Rules for optimization of biocatalysts in organic solvents. Biotechnol. Bioeng. 1987, 30, 81-87
229. Ikeda, M. Public health problems of organic solvents. Toxicol. Lett. 1992, 64/65, 191-201
230. Wells, J. A. and Estell, D. A. Subtilisin: An enzyme designed to be engineered. Trends Biochem. Sci. 1988, 13, 291-297
231. Abrahmsen, L., Tom, J., Burnier, J., Butcher, K. A., Kossiakoff, A., and Wells, J. A. Engineering subtilisin and its substrates for efficient ligation of peptide bonds in aqueous solution. Biochemistry 1991, 30, 4151-4159
232. Bonneau, P. R., Graycar, T. P., Estell, D. A., and Jones, J. B. Alteration of the specificity of subtilisin BPN′ by site-directed mutagenesis in its S1 and S1′ binding sites. J. Am. Chem. Soc. 1990, 113, 1026-1030
233. Carter, P., Abrahamsen, L., and Wells, J. A. Probing the mechanism and improving the rate of substrate-assisted catalysis in subtilisin BPN′. Biochemistry 1991, 30, 6142-6148
234. Estell, D. A., Graycar, T. P., Miller, J. V., Powers, D. B., Burnier, J. P., Ng, P. G., and Wells, J. A. Probing steric and hydrophobic effects on enzyme-substrate interactions by protein engineering. Science 1986, 233, 659-663
235. Fersht, A. R., Shi, J. P., Knill-Jones, J., Lowe, D. M., Willkinson, A. J., Blow, D. M., Brick, P., Waye, M. M. Y., and Winer, G. Hydrogen bonding and biological specificity analyzed by protein engineering. Nature 1985, 314, 235-238
236. Perry, L. J. and Wetzel, R. Disulfide bond engineered into T4-lysozyme-stabilization of the protein toward thermal inactivation. Science 1984, 226, 555-557
237. Groen, H., Bech, L. M., Branner, S., and Breddam, K. A highly active oxidation-resistant mutant subtilisin-like enzyme produced by a combination of site-directed mutagenesis and chemical modification. Eur. J. Biochem. 1990, 194, 897-901
238. Narhi, L. O., Stabinsky, Y., Levitt, M., Miller, L., Sachdev, R., Finley, S., Park, S., Kolvenbach, C., Arakawa, T., and Zukowski, M. Enhanced stability of subtilisin by three point mutations. Biotechnol. Appl. Biochem. 1991, 13, 12-24
239. Wong, C.-H., Chen, S.-T., Hennen, W. J., Bibbs, J. A., and Yang, Y.-F. Enzymes in organic synthesis: The use of subtilisin and a highly stable mutant derived from multiple site-specific mutations. J. Am. Chem. Soc. 1990, 112, 945-953
240. Zhong, Z., Liu, L.-C., Dinterman, L. M., Finkelman, M. A. J., Mueller, W. T., Rollence, M. L., Whitlow, M., and Wong, C.-H. Engineering subtilisin for reaction in dimethylformamide. J. Am. Chem. Soc. 1991, 113, 683-684
241. Wong, C.-H., Schuster, M., Wang, P., and Sears, P. Enzymatic synthesis of N- and O-linked glycopeptides. J. Am. Chem. Soc. 1993, 14, 5896-5903
242. Chen, K., Robinson, A. C., Van Pam, M. E., Martinez, P., Economou, C., and Arnold, F. H. Enzyme engineering for nonaqueous solvents. II. Additive effects of mutation on the stability and activity of subtilisin E in polar organic media. Biotechnol. Prog. 1991, 7, 125-129
243. Martinez, P. and Arnold, F. H. Surface charge substitutions increase the stability of α-lytic protease in organic solvents. J. Am. Chem. Soc. 1991, 113, 6336-6337
244. Wong, C.-H. Engineering enzymes for chemoenzymatic synthesis. Part 2. Modified proteases for peptide synthesis. Trends Biotechnol. 1992, 10, 378-382
245. Roig, M. G. and Kennedy, J. F. Perspectives for chemical modification of enzymes. CRC Crit. Rev. Biotechnol. 1992, 12, 391-412
246. Nakatsuka, T., Sasaki, T., and Kaiser, E. Peptide segment coupling catalysed by the semisynthetic enzyme thiolsubtilisin. J. Am. Chem. Soc. 1987, 109, 3808-3810
247. Wu, Z.-P. and Hilvert, D. Conversion of a protease into an acyl transferase. Selenolsubtilisin. J. Am. Chem. Soc. 1989, 111, 4513-4514
248. West, J. B., Scholten, J., Stolwich, N. J., Hogg, J. L., Scott, A. I., and Wong, C.-H. Modification of proteases to esterases for peptide synthesis: Methylchymotrypsin. J. Am. Chem. Soc. 1988, 110, 3709-3710
249. West, J. B., Hennen, W. J., Lalonde, J. L., and Wong, C.-H. Enzymes as synthetic catalysts: Active site considerations of natural and modified chymotrypsin. J. Am. Chem. Soc. 1990, 112, 5313-5320
250. Wang, P., Hill, T. G., Wartchow, C. A., Huston, M. E., Oehler, L. M., Bradley Smith, M., Bednarski, M. D., and Callstrom, M. R. New carbohydrate-based materials for the stabilization of proteins. J. Am. Chem. Soc. 1992, 114, 378-380
251. Khmelnitsky, Y. L., Welch, S. H., Clark, D. S., and Dordick, J. S. Salts dramatically enhance activity of enzymes suspended in organic solvents. J. Am. Chem. Soc. 1994, 116, 2647-2648
252. Paradkar, V. M. and Dordick, J. S. Aqueous-like activity of α-chymotrypsin dissolved in nearly anhydrous organic solvents. J. Am. Chem. Soc. 1994, 116, 5009-5010
253. St. Clair, N. L., and Navia, M. A. Cross-linked enzyme crystals as robust biocatalysts. J. Am. Chem. Soc. 1992, 114, 7314-7316
254. Persichetti, R. A., St. Clair, N. L., Griffith, J. P., Navia, M. A., and Margolin, A. L. Cross-linked enzyme crystals (CLECs) of thermolysin in the synthesis of peptides. J. Am. Chem. Soc. 1995, 117, 2732-2737
255. Hirschmann, R., Smith III, A. B., Taylor, C. M., Benkovic, P. A., Taylor, S. D., Yager, K. M., Sprengeler, P. A., and Benkovic, S. J. Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. Science 1994, 265, 234-237
256. Jacobsen, J. R. and Schultz, P. G. Antibody catalysis of peptide bond formation. Proc. Natl Acad. Sci. (U.S.A.) 1994, 91, 5888-5892
257. α-protecting groups of amino acids. Biocatalysis 1994, 8, 289-307
258. Ricca, J. M. and Crout, D. H. G. Peptide synthesis catalysed by α-chymotrypsin in organic solvents. J. Chem. Soc. Perkin. Trans. 1. 1989, 3, 2126-2128
259. Slomczynska, U. and Leplawy, T. Peptide synthesis catalysed by α-chymotrypsin in ultra low water media. In: Peptides 1988 (Jung, G. and Bayer, E., Eds.). Walter de Gruyter, Berlin, 253-254
260. Hailing, P., Eichorn, U., Kuhl, P. and Jakubke, H.-D. Thermodynamics of solid to solid conversion and its application to enzymatic peptide synthesis. Enzyme Microb. Technol. 1995, in press
261. Kuhl, P., Eichorn, U., and Jakubke, H.-D. Enzymatic peptide synthesis in microaqueous, solvent-free systems. Biotechnol. Bioeng. 1995, 45, 276-278
262. Cerovsky, V. Protease-catalysed peptide synthesis in solvent-free system. Biotechnol. Tech. 1992, 6, 155-160
263. Gill, I. and Vulfson, E. N. Enzymatic synthesis of short peptides in heterogeneous mixtures of substrates. J. Am. Chem. Soc. 1993, 115, 3348-3349
264. Gill, I. and Vulfson, E. N. Enzymatic catalysis in heterogeneous eutectic mixtures of substrates. Trends Biotechnol. 1994, 12, 118-122
265. López-Fandiño, R., Gill, I., and Vulfson, E. N. Enzymatic catalysis in heterogeneous mixtures of substrates. The role of the liquid phase and the effects of "adjuvants". Biotechnol. Bioeng. 1994, 43, 1016-1023
266. López-Fandiño, R., Gill, I., and Vulfson, E. N. Protease-catalysed synthesis of oligopeptides in heterogeneous substrate mixtures. Biotechnol. Bioeng. 1994, 43, 1024-1030
267. Gill, I., López-Fandiño, R., Jorba, X., and Vulfson, E. N. New approaches to the enzymatic production of oligopeptides: Synthesis of the "Delicious Peptide" and its fragments. In: Advances in Bioprocess Engineering (Galindo, E. and Ramirez, O. T., Eds.). Kluwer Academic, Dordrecht, Berlin 1994, 485-488
268. Jorba, X., Gill, I., and Vulfson, E. N. Enzymatic synthesis of the delicious peptide fragments in eutectic mixtures. Submitted
269. Gill, I., López-Fandiño, R., and Vulfson, E. N. Enzymatic catalysis in heterogenous eutectic media: A physico-chemical study. In preparation
270. α-unprotected dipeptide stereoisomers and analogues. In: Peptides 1990 (Giralt, E. and Andreu, D., Eds.). ESCOM Science, 1990, 299-300
271. Gill, I. and Vulfson, E. N. Facile enzymatic synthesis of N-acyl-enkephalin amides. J. Chem. Soc. Perkin Trans. 1. 1992, 6, 667-668
272. Gill, I., López-Fandiño, R., and Vulfson, E. N. Enzymatic oligopeptide synthesis using a minimal protection strategy: Sequential assembly of a growing oligopeptide chain. J. Am. Chem. Soc. Accepted for publication
273. Nakanishi, K., Takeuchi, A., and Matsuno, R. Long term continuous synthesis of aspartame precursor in a column reactor with an immobilized thermolysin. Appl. Microbiol. Biotechnol. 1990, 32, 633-636
274. Cramer, S. M. and Horvath, C. Peptide synthesis and deamidation with chemically modified immobilized carboxypeptidase Y. Enzyme Microb. Technol. 1989, 11, 74-79
275. Florsheimer, A., Kula, M.-R., Schultz, H.-J., and Wandrey, C. Continuous production of kyotorphin. Biotechnol. Bioeng. 1989, 33, 1400-1405
276. Hermann, G., Schwarz, A., Wandrey, C., Kula, M. R., Knaup, G., Drauz, K. H., and Berndt, H. Scale up of enzymatic peptide synthesis in an enzyme membrane reactor. Biotechnol. Appl. Biochem. 1991, 13, 346-353
277. Schwarz, A., Wandrey, C., Steinke, D., and Kula, M. R. A two-step enzymatic synthesis of dipeptides. Biotechnol. Bioeng. 1992, 39, 132-140
278. Kimura, Y., Nakanishi, K., and Matsuno, R. Synthesis of peptides consisting of essential amino acids by a three reactor system using three proteinases and an organic solvent. Agric. Biol. Chem. 1990b, 54, 3331-3333
279. Kimura, Y., Yoshida, T., Muraya, K., Nakanishi, K., and Matsuno, R. Continuous synthesis of a tripeptide by successive condensation and transesterification catalysed by two immobilized proteases in organic solvent. Agric. Biol. Chem. 1990a, 54, 1433-1440
280. Waldmann, H. and Sebastian, D. Enzymatic protecting group techniques. Chem. Rev. 1994, 94, 911-937
281. Hermann, P. Enzymatic manipulation of protecting groups: More than deprotection. Biomed. Biophys. Acta 1991, 50, S19-S31
282. Richards, A. O'L., Gill, I., and Vulfson, E. N. Continuous enzymatic production of oligopeptides: Synthesis of an enkephalin pentapeptide in a multistage bioreactor. Enzyme Microb. Technol. 1993, 15, 928-935