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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3843

Title: Experimental and computational studies of the recognition of amino acids by galactosyl-imine and -amine derivatives: An attempt to understand the lectin-carbohydrate interactions
Authors: AHUJA, R
SINGHAL, NK
RAMANUJAM, B
RAVIKUMAR, M
RAO, CP
Keywords: structural basis
crystal-structure
photodynamic therapy
purification
binding
complex
specificity
seeds
receptor
domain
Issue Date: 2007
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 72(9), 3430-3442
Abstract: A galactosyl-naphthyl-imine-based derivative, 1-(beta-D-galactopyranosyl-1'-deoxy-1'-iminomethyl)-2-hydroxynaphthalene (GNI), and a galactosyl-naphthyl-amine-based derivative, 1-(galactopyranosyl-1'-deoxy-1'-aminomethyl)-2-hydroxynaphthalene (GNA), possessing an ONO binding core were studied for their recognition of naturally occurring amino acids using fluorescence and absorption spectroscopy, and the corresponding association constants were derived for the complexes formed. The complexes formed between GNI/GNA and amino acids were supported by electrospray ionization mass spectrometry (ESI/MS). The structures of the complexes were optimized by computational studies using density functional theory, and stabilization energies were computed for the complexes to substantiate the interactions present between GNI/GNA and amino acid. The interactions were found to be primarily hydrogen bonding in nature. These interactions are reminiscent of those present in the lectin-carbohydrate and glycosidase substrate. Thus, the carbohydrate moiety present in GNI shows high specificity toward the -COOH group of the amino acid, which may be relevant to such interactions present between the carbohydrates and the polypeptides.
URI: http://dx.doi.org/10.1021/jo0700979
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3843
http://hdl.handle.net/10054/3843
ISSN: 0022-3263
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