Document Detail

A methodological study of the enzymatic synthesis of the tripeptide Z-Cys(Bzl)-Tyr-Ile-OtBu.
MedLine Citation:
PMID:  1821169     Owner:  NLM     Status:  MEDLINE    
The tripeptide Z-Cys(Bzl)-Tyr-Ile-OtBu (I) has been synthesized by papain, chymotrypsin and thermolysin catalysis using two different strategies: a) starting from the C-terminal amino acid and b) starting from the N-terminal amino acid. The optimum reaction conditions for obtaining the peptides Z-Tyr-Ile-OtBu (II), Z-Cys(Bzl)-Tyr-OtBu (III) and Z-Cys(Bzl)-Tyr-Ile-OtBu (I) were established after analyses of the effects of pH, reaction time, concentrations of buffer, enzyme and substrates, relative proportions of the carboxyl to amine components and nature of the organic solvent on the coupling yield. The highest yields obtained for II and I using chymotrypsin and papain as catalysts were 74% and 45%, respectively. Starting from the N-terminal amino acid, and using papain and thermolysin as catalysts, the yields obtained were 91% for III and 92% for I. The effects of amine- and carboxyl-protecting groups on the extent of dipeptide synthesis catalyzed by chymotrypsin were also studied.
A Irokawa; M Tominaga
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Peptide research     Volume:  4     ISSN:  1040-5704     ISO Abbreviation:  Pept. Res.     Publication Date:    1991 Nov-Dec
Date Detail:
Created Date:  1992-08-14     Completed Date:  1992-08-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8913494     Medline TA:  Pept Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  340-6     Citation Subset:  IM    
University of São Paulo.
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MeSH Terms
Chymotrypsin / metabolism
Oligopeptides / biosynthesis*,  chemistry
Oxytocin / chemistry
Papain / metabolism
Thermolysin / metabolism
Reg. No./Substance:
0/Oligopeptides; 50-56-6/Oxytocin; 52668-03-8/(phenylmethoxy)carbonylcysteinyl(phenylmethyl)-tyrosyl-isoleucine tert-butyl ester; EC; EC; EC

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