Document Detail


Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin.
MedLine Citation:
PMID:  23538879     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A novel oxalic amide-linked bisporphyrinate 1has been designed and synthesized, which shows chiral recognition ability for amino acid ethyl esters. The structure of complex 1·(D-Phe-OEt)(L-Phe-OEt) has been solved by X-ray crystallography. It reveals the following information: bisporphyrin unit adopts anti-configuration; compound 1forms 1: 2 complex with amino acid ethyl esters; one important hydrogen bond is formed between the coordinated nitrogen of amino acid ester and carbonyl oxygen in the amide group. The chiral recognition mechanism has been further investigated by UV-Vis spectra, (1)H NMR and DFT/TDDFT calculations.
Authors:
Jiaxun Jiang; Zhiqiang Feng; Baozhen Liu; Chuanjiang Hu; Yong Wang
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Dalton transactions (Cambridge, England : 2003)     Volume:  42     ISSN:  1477-9234     ISO Abbreviation:  Dalton Trans     Publication Date:  2013 Jun 
Date Detail:
Created Date:  2013-05-10     Completed Date:  2013-10-21     Revised Date:  2013-11-07    
Medline Journal Info:
Nlm Unique ID:  101176026     Medline TA:  Dalton Trans     Country:  England    
Other Details:
Languages:  eng     Pagination:  7651-9     Citation Subset:  IM    
Affiliation:
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, PR China.
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MeSH Terms
Descriptor/Qualifier:
Amides / chemical synthesis,  chemistry
Amino Acids / chemistry,  isolation & purification*
Binding Sites
Circular Dichroism
Crystallography, X-Ray
Esters / chemistry,  isolation & purification
Magnetic Resonance Spectroscopy
Porphyrins / chemical synthesis,  chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Amides; 0/Amino Acids; 0/Esters; 0/Porphyrins

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


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