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

TitleBicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres
Publication TypeJournal Article
Year of Publication2011
AuthorsKale, SS, Chavan, ST, Sabharwal, SG, Puranik, VG, Sanjayan, GJ
JournalOrganic & Biomolecular Chemistry
Volume9
Issue21
Pagination7300-7302
Date PublishedSEP
ISSN1477-0520
Abstract

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 a-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.

DOI10.1039/c1ob06215h
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.696

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry