Document Detail


Enantio- and chemoselective differentiation of protected α-amino acids and β-homoamino acids with a single copper(II) host.
MedLine Citation:
PMID:  22592912     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The association between an achiral copper(II)-containing host 1 and chiral carboxylates has been expanded beyond previous studies to new chiral carboxylate guests, both α-amino acids and β-homoamino acids. The observed exciton-coupled circular dichroism (ECCD) signals for the enantiomers of each carboxylate were equal and opposite, and these signals differed in size and shape between the individual amino acids. Linear discriminant analysis (LDA) was applied as a statistical analysis technique to differentiate the amino acids, both enantioselectively and chemoselectively, giving the absolute configuration and identity of the amino acid. The identity of each of the α-amino acids and β-homoamino acids were determined independently by LDA, and then the two were considered together. Each of these analyses showed good differentiation of the amino acid guests with the use of only one host molecule.
Authors:
Leo A Joyce; James W Canary; Eric V Anslyn
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2012-05-16
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  18     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2012 Jun 
Date Detail:
Created Date:  2012-06-18     Completed Date:  2012-09-28     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  8064-9     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712, USA.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry*
Carboxylic Acids / chemistry*
Circular Dichroism
Copper / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM77437/GM/NIGMS NIH HHS; R01 GM077437/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Carboxylic Acids; 0/Organometallic Compounds; 7440-50-8/Copper
Comments/Corrections

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