Document Detail


Synthesis of ( 2S, 4S)-4-phenylamino-5-oxoproline derivatives.
MedLine Citation:
PMID:  12395185     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The paper describes the synthesis of ( 2S, 4S)-4-(N-Ts)- and ( 2S, 4S)-4-(N-Boc)-phenylamino-5-oxoprolines (pyroglutamic acid). These derivatives have been shown to be useful for synthesis of their amides and peptides in spite of steric hindrances caused by bulky groups adjacent to the reaction centre. Under the conditions applied no lactam ring opening and no loss of stereochemical integrity of any of the chiral centres were observed, which has been confirmed by NMR techniques.
Authors:
I A Nizova; V P Krasnov; G L Levit; M I Kodess
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Amino acids     Volume:  22     ISSN:  0939-4451     ISO Abbreviation:  Amino Acids     Publication Date:  2002  
Date Detail:
Created Date:  2002-10-23     Completed Date:  2003-05-29     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9200312     Medline TA:  Amino Acids     Country:  Austria    
Other Details:
Languages:  eng     Pagination:  179-86     Citation Subset:  IM    
Affiliation:
Institute of Organic Synthesis, Ural Division of Russian Academy of Sciences, Ekaterinburg, Russia.
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MeSH Terms
Descriptor/Qualifier:
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrrolidonecarboxylic Acid / analogs & derivatives,  chemical synthesis*,  chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
98-79-3/Pyrrolidonecarboxylic Acid

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