Document Detail

Assignment of absolute configuration of chiral carboxylic acids via exciton-coupled CD treatment: 4-phenylthioproline as a case study.
MedLine Citation:
PMID:  12125029     Owner:  NLM     Status:  PubMed-not-MEDLINE    
The 4-hydroxybenzoate chromophore was used as an exciton reporter group for the assignment of the absolute configuration of a chiral carboxylic acid of pharmaceutical interest, (-)-(2S,4S)-4-phenylthioproline, precursor of the ACE-inhibitor zofenopril. The nondegenerate coupling with the preexisting phenylthio chromophore was observed. A detailed conformational analysis, accomplished by means of (1)H-NMR NOESY and semiempirical PM3 computational methods, and quantitative CD calculations were necessary to substantiate the assignment based on a weak experimental couplet.
Lorenzo Di Bari; Serena Mannucci; Gennaro Pescitelli; Piero Salvadori
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chirality     Volume:  14     ISSN:  0899-0042     ISO Abbreviation:  Chirality     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-07-18     Completed Date:  2002-08-15     Revised Date:  2003-11-03    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  United States    
Other Details:
Languages:  eng     Pagination:  611-7     Citation Subset:  -    
Copyright Information:
Copyright 2002 Wiley-Liss, Inc.
Centro di Studio del CNR per le Macromolecole Stereordinate e Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Pisa, Italy.
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