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    
Abstract/OtherAbstract:
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.
Authors:
Lorenzo Di Bari; Serena Mannucci; Gennaro Pescitelli; Piero Salvadori
Related Documents :
4087199 - Shifts in the apparent ionization constant of the carboxylic acid groups of gelatin.
15595449 - Nmr assignments of the major cannabinoids and cannabiflavonoids isolated from flowers o...
17805689 - Synthesis oftrans-3-hexadecenoic acid and oftrans-3-hexadecenoic-1-c(14) acid.
7893689 - Mechanism of the reaction catalyzed by mandelate racemase: importance of electrophilic ...
20705969 - The synthesis of silica nanotubes through chlorosilanization of single wall carbon nano...
16830499 - Synthesis and hplc evaluation of carboxylic acid phases on a hydride surface.
10552809 - Release of deuterated nonenal during beer aging from labeled precursors synthesized in ...
9753449 - Modulation of the positional specificity of lecithin-cholesterol acyltransferase by the...
3131689 - The role of serine and glutamine in the metabolism of malignant bone tumors and their s...
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.
Affiliation:
Centro di Studio del CNR per le Macromolecole Stereordinate e Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Pisa, Italy.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

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


Previous Document:  Generic fast gradient liquid chromatography/tandem mass spectrometry techniques for the assessment o...
Next Document:  Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic...