Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres

This communication describes a general synthetic route to bicyclic amino acid-carbohydrate-conjugates, which would be useful as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres. The synthesis was achieved in 12 steps starting from D-glucose. The striking features of thi...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-11, Vol.9 (21), p.7300-7302
Main Authors: Kale, Sangram S, Chavan, Sanjay T, Sabharwal, Sushma G, Puranik, Vedavati G, Sanjayan, Gangadhar J
Format: Article
Language:English
Subjects:
Amino Acids, Cyclic - chemistry
Carbohydrates - chemistry
Crystallography, X-Ray
Ethanolamines - chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This communication describes a general synthetic route to bicyclic amino acid-carbohydrate-conjugates, which would be useful as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres. The synthesis was achieved in 12 steps starting from D-glucose. The striking features of this system are the bicyclic rigid core displaying an α-amino acid side chain and hydroxyethylamine moiety--both of which would be potentially important for receptor interactions, leading to various biomedical responses, as described in the literature. Crystal structure investigation suggested extensive intermolecular hydrogen-bonding interactions in this system, involving the backbone amide and hydroxyl groups.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob06215h