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Insights into the role of the aromatic residue in galactose-binding sites: MP2/6-311G++** study on galactose- and glucose-aromatic residue analogue complexes

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Title Insights into the role of the aromatic residue in galactose-binding sites: MP2/6-311G++** study on galactose- and glucose-aromatic residue analogue complexes
 
Creator SUJATHA, MS
SASIDHAR, YU
BALAJI, PV
 
Subject cation-pi interactions
ricin-b chain
crystal-structures
hydrogen-bonds
carbohydrate-binding
computational design
fluorodeoxy sugars
2-gamma subdomain
escherichia-coli
lectin structure
 
Description The presence of an aromatic residue (Trp, Phe, Tyr) facing the nonpolar face of galactose is a common feature of galactose-specific lectins. The interactions such as those between the C-H groups of galactose and the pi-electron cloud of aromatic residues have been characterized as weak hydrogen bonds between soft acids and soft bases, largely governed by dispersive and charge transfer interactions, An analysis of the binding sites of several galactose-specific lectins revealed that the spatial position-orientation of galactose relative to the binding site aromatic residue varies substantially. The effect of variations in position-orientations of galactose on the interaction energies of galactose-aromatic residue complexes has not been determined so far. In view of this, MP2/6-311G++** calculations were performed on galactose- and glucose-aromatic residue analogue complexes in eight position-orientations. The results show that the strength of the C-H... it interactions in galactose-aromatic residue complexes is comparable to that of a hydrogen bond. Rather than the type of aromatic residue, the position-orientation of the saccharide appears to be more critical in determining the strength of their interactions. Earlier studies have found the binding site aromatic residue to be critical, but its role was not clear, This study shows that the aromatic residue is important for discriminating galactose from glucose, in addition to its contribution to binding energy.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T08:28:07Z
2011-12-26T12:48:17Z
2011-12-27T05:48:04Z
2011-07-14T08:28:07Z
2011-12-26T12:48:17Z
2011-12-27T05:48:04Z
2005
 
Type Article
 
Identifier BIOCHEMISTRY, 44(23), 8554-8562
0006-2960
http://dx.doi.org/10.1021/bi050298b
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3909
http://hdl.handle.net/10054/3909
 
Language en