Document Detail


Trypsin-catalyzed synthesis of dipeptide containing alpha-aminoisobutyric acid using p- and m-(amidinomethyl)phenyl esters as acyl donor.
MedLine Citation:
PMID:  18451559     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Two series of inverse substrates, p- and m-(amidinomethyl)phenyl esters derived from N-(tert-butyloxycarbonyl)amino acid, were prepared as acyl donor components for enzymatic peptide synthesis. They were found to be readily coupled with an acyl acceptor such as L-alanine p-nitroanilide to produce dipeptide. An alpha-aminoisobutyric acid containing dipeptide was especially obtained in satisfactory yield. Streptomyces griseus trypsin was a more efficient catalyst than the bovine trypsin. The optimum condition for the coupling reaction was studied by changing the organic solvent, pH, and acyl acceptor concentration. It was found that the enzymatic hydrolysis of the resulting product was negligible.
Authors:
Haruo Sekizaki; Kunihiko Itoh; Akiyoshi Shibuya; Eiko Toyota; Mareshige Kojoma; Kazutaka Tanizawa
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  56     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-05-02     Completed Date:  2008-07-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  688-91     Citation Subset:  IM    
Affiliation:
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido, Japan. sekizaki@hoku-iryo-u.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Acylation
Amidines / chemistry*
Aminoisobutyric Acids / chemistry*
Animals
Catalysis
Cattle
Dipeptides / chemical synthesis*
Hydrogen-Ion Concentration
Indicators and Reagents
Magnetic Resonance Spectroscopy
Spectrophotometry, Infrared
Spectroscopy, Fourier Transform Infrared
Streptomyces griseus / enzymology
Structure-Activity Relationship
Trypsin / chemistry*
Chemical
Reg. No./Substance:
0/Amidines; 0/Aminoisobutyric Acids; 0/Dipeptides; 0/Indicators and Reagents; 62-57-7/2-aminoisobutyric acid; EC 3.4.21.4/Trypsin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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