Document Detail


Weak acid-catalyzed pyrrolidone carboxylic acid formation from glutamine during solid phase peptide synthesis. Minimization by rapid coupling.
MedLine Citation:
PMID:  7118385     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Formation of pyrrolidone carboxylic acid (pyroglutamic acid) residues from amino-terminal glutaminyl residues in peptides was shown to be catalyzed by weak acids, but not by strong acids. During dicyclohexylcarbodiimide-mediated coupling reactions the N alpha-protected amino acid reagent accelerated this cyclization and resulted in a significant amount of chain termination. The side reaction could be minimized by accelerating the coupling reaction and simultaneously reducing the time of exposure to weak acids. The most effective procedure was to couple in dimethylformamide with the preformed symmetric anhydride of the amino acid.
Authors:
R D Dimarchi; J P Tam; S B Kent; R B Merrifield
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  19     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1982 Jan 
Date Detail:
Created Date:  1982-12-02     Completed Date:  1982-12-02     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  88-93     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Chemical Phenomena
Chemistry
Dicyclohexylcarbodiimide
Dimethylformamide
Glutamine*
Oligopeptides / chemical synthesis*
Pyrrolidinones*
Pyrrolidonecarboxylic Acid*
Trifluoroacetic Acid
Grant Support
ID/Acronym/Agency:
AM02160/AM/NIADDK NIH HHS
Chemical
Reg. No./Substance:
0/Oligopeptides; 0/Pyrrolidinones; 538-75-0/Dicyclohexylcarbodiimide; 56-85-9/Glutamine; 68-12-2/Dimethylformamide; 76-05-1/Trifluoroacetic Acid; 98-79-3/Pyrrolidonecarboxylic Acid

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


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