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Peptide Chirality Sensing by a Cyclodextrin-Polythiophene Conjugate.
MedLine Citation:
PMID:  22829530     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A new cyclodextrin-polythiophene conjugate (CDPT) has been prepared by attaching permethyl-α-cyclodextrins to polythiophene (PT) through a hexamethylene tether. Circular dichroism spectral examination of CDPT revealed that only a weak positive Cotton effect (Δε=0.1 M(-1)  cm(-1) ) was induced at the main band of the PT in dimethyl sulfoxide and similarly weak bisignate signals in pure and aqueous methanol solutions, which indicates that the α-cyclodextrins appended to PT with a long tether are ineffective in inducing a homochiral structure in the PT backbone. Nevertheless, enantiomeric amino acids and dipeptides added to an aqueous methanolic solution of CDPT caused chirality-dependent hypochromic changes in the UV/Vis spectra, which enabled us to sense these species and quantitatively determine the enantioselectivity by observing the difference in absorbance upon interaction with pairs of enantiomers. Enantiomeric d,d/l,l-dipeptide pairs rather than D/L-amino acid pairs were better differentiated in general, the highest dd/ll selectivity of 13.7 being observed for Phe-Phe.
Authors:
Gaku Fukuhara; Yoshihisa Inoue
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-7-24
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-7-25     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871 (Japan), Fax: (+81) 668-797-923. gaku@chem.eng.osaka-u.ac.jp.
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