Document Detail


Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids.
MedLine Citation:
PMID:  15635648     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A number of protected proline-containing dipeptides Boc-Xaa-Pro-OBu(t) were converted via epimerization-free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc-Xaa-Glp-OBu(t). The latter were subjected to oxidative Hoffman-type rearrangement induced by PhI[OC(O)CF3]2 to give N-(aminoacyl)-pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10-membered-ring dilactams derived from 1,4-diaminobutyric and glutamic acids in practicable yields.
Authors:
A N Chulin; I L Rodionov; L K Baidakova; L N Rodionova; T A Balashova; V T Ivanov
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of peptide science : an official publication of the European Peptide Society     Volume:  11     ISSN:  1075-2617     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2005 Mar 
Date Detail:
Created Date:  2005-02-28     Completed Date:  2005-11-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  175-86     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2004 European Peptide Society and John Wiley & Sons, Ltd.
Affiliation:
Branch of Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Pushchino, Moscow Region, Russia.
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MeSH Terms
Descriptor/Qualifier:
Aminoacylation
Aminobutyric Acids / chemistry*
Glutamic Acid / analogs & derivatives*,  chemical synthesis*,  chemistry
Molecular Structure
Ornithine / chemistry
Oxidation-Reduction
Peptides, Cyclic / chemical synthesis*,  chemistry*
Pyrrolidonecarboxylic Acid / chemistry
Chemical
Reg. No./Substance:
0/Aminobutyric Acids; 0/Peptides, Cyclic; 56-86-0/Glutamic Acid; 7006-33-9/Ornithine; 98-79-3/Pyrrolidonecarboxylic Acid

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