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1,3-Di-peptido-conjugates of calix[4]arene and its di-OCH(3) derivatives: Synthesis, characterization and phosphate recognition

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Title 1,3-Di-peptido-conjugates of calix[4]arene and its di-OCH(3) derivatives: Synthesis, characterization and phosphate recognition
 
Creator DEY, M
ALI, A
ACHARYA, A
RAO, CP
 
Subject amino-acid
calixarenes
complexes
rim
peptido-conjugates of calix[4]arene
hmqc
binding core
conformational mobility
phosphate binding
 
Description Novel double-armed peptido-conjugates of calix[4]arene have been developed on the lower rim of the macrocycle. The functional group pendants exhibit conformational bend through the involvement of 11-atom N-H center dot center dot center dot O hydrogen bond inscribed in a 14-atom O-H center dot center dot center dot O interaction. As a result, only the terminal -COOR and -COOH groups are exposed to the environment, but not the amide moiety. The cone-conformation of the calix[4]arene is further stabilized through the O-H center dot center dot center dot O interactions at the lower rim. In effect, the conjugates exhibit a binding core at the lower rim along with hydrophobic cavity formed by the enclosure of arene moieties. Conformational mobility induced by the replacement of lower rim phenolic-OH by -OCH(3) has also been demonstrated by variable temperature NMR studies in case of the corresponding - OCH(3) derivatives. Differential receptor binding characteristics of these conjugates towards phosphate are demonstrated using absorption spectroscopy. The negatively charged phosphate group is received preferentially by the carboxylic terminal over the ester terminal conjugate.
 
Publisher COUNCIL SCIENTIFIC & INDUSTRIAL RES
 
Date 2011-07-20T11:09:41Z
2011-12-26T12:51:27Z
2011-12-27T05:36:34Z
2011-07-20T11:09:41Z
2011-12-26T12:51:27Z
2011-12-27T05:36:34Z
2010
 
Type Article
 
Identifier INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 49(8), 1098-1108
0376-4699
http://dspace.library.iitb.ac.in/xmlui/handle/10054/5452
http://hdl.handle.net/10054/5452
 
Language en