Lipase-catalyzed synthesis of peptides containing D-amino acid

Enzyme and Microbial Technology

Volumn 23, Issue 3-4, 1998, Pages 211-215

  So, Jin Eon ^a   Kang, Seung Hyun ^a   Kim, Byung Gee ^a  

^a Seoul National University   (South Korea)

Author keywords

D amino acid; Organic solvent; Peptide synthesis; Porcine pancreatic lipase (PPL)

Indexed keywords

AMINO ACIDS; CATALYSIS; ENZYMES; ESTERS; SUBSTRATES;

LIPASE; PEPTIDES;

BIOSYNTHESIS;

DEXTRO AMINO ACID; DIPEPTIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; ENZYME SPECIFICITY; ISOMER; NONHUMAN; PEPTIDE SYNTHESIS; SWINE;

EID: 0032143575     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(98)00051-9     Document Type: Article

References (19)

1. Kullman W. Enzymatic Peptide Synthesis. 1987;CRC Press, Boca Raton, FL.
2. Gill I., López-Fandiño R., Vulfson E. Enzymatic oligopeptide synthesis using a minimal protection strategy Sequential assembly of a growing oligopeptide chain . J. Am. Chem. Soc. 117:1995;6175-6181.
3. Capellas M., Benaiges M.D., Caminal G., Gonalez G., Lopez-Santin J., Clapés P. Enzymatic synthesis of a CCK-8 tripeptide fragment in organic media. Biotechnol. Bioeng. 50:1996;700-708.
4. Nishiro N., Xu M., Mihara H., Fujimoto T. Use of hexafluoroisopropyl alcohol in tryptic condensation of partially protected precursor of α-melanocyte stimulating hormone (α-MSH). Tetrahedron Lett. 30:1992;3137-3140.
5. Kunugi S., Koyasu A., Takahashi S., Oda K. Peptide condensation activity of a neutral protease from Vibrio sp. Tl800 (Vimelysin). Biotechnol. Bioeng. 53:1997;387-390.
6. Sears P., Schuster M., Wang P., Witte K., Wong C.-H. Engineering subtilisin for peptide coupling Studies on the effects of counterions and site-directed modifications on the stability and specificity of the enzyme . J. Am. Chem. Soc. 116:1994;6521-6530.
7. Itoh K., Sekizaki H., Toyota E., Fujiwara N., Tanizawa K. Application of inverse substrates to trypsin-catalyzed peptide synthesis. Bioorg. Chem. 24:1996;59-68.
8. Margolin A.L., Klibanov A.M. Peptide synthesis catalyzed by lipases in anhydrous organic solvents. J. Am. Chem. Soc. 109:1987;3802-3804.
9. Matos J.R., West J.B., Wong C.-H. Lipase-catalyzed synthesis of peptides Preparation of a penicillin G precursor and other peptides . Biotechnol. Lett. 4:1987;233-236.
10. Kawashiro K., Kaiso K., Minato D., Sugiyama S., Hayashi H. Lipase-catalyzed peptide synthesis using Z-amino acid esters as acyl donors in aqueous water-miscible organic solvents. Tetrahedron. 49:1993;4541-4548.
11. Asano Y., Nakazawa A., Kato Y., Kondo K. Properties of a novel D-stereospecific aminopeptidase from Ochrobactrum anthropi. J. Biol. Chem. 24:1989;14233-14239.
12. West J.B., Wong C.-H. Enzyme-catalyzed irreversible formation of peptides containing D-amino acids. J. Org. Chem. 51:1986;2728-2735.
13. Margolin A.L., Tia D.F., Klibanov A.M. Incorporation of D-amino acids into peptides via enzymatic condensation in organic solvents. J. Am Chem. Soc. 109:1987;7885-7887.
14. Mingarro I., González-Navarro H., Braco L. Trapping of different lipase conformers in water-restricted environments. Biochemistry. 35:1996;9935-9944.
15. Kitaguchi H., Fitzpatrick P.A., Huber J.E., Klibanov A.M. Enzymatic resolution of racemic amines Crucial role of the solvents . J. Am. Chem. Soc. 111:1989;3094-3095.
16. Kim J., Kim B.-G. Effect of the hydration state of supports before lyophilization on subtilisin-A activity in organic media. Biotechnol. Bioeng. 50:1996;687-692.
17. 1 for peptide synthesis in aqueous-organic media. Bull. Chem. Soc. Jpn. 66:1993;3693-3698.
18. Verger R. 'Interfacial activation' of lipases Facts and artifacts . TIBTECH. 15:1997;32-38.
19. Rich J.O., Dordick J.S. Controlling subtilisin activity and selectivity in organic media by imprinting with nucleophilic substances. J. Am. Chem. Soc. 119:1997;3245-3252.