Document Detail


Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres.
MedLine Citation:
PMID:  21915421     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Sangram S Kale; Sanjay T Chavan; Sushma G Sabharwal; Vedavati G Puranik; Gangadhar J Sanjayan
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-9-14
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  -     Publication Date:  2011 Sep 
Date Detail:
Created Date:  2011-9-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Division of Organic Chemistry, National Chemical Laboratory, Dr Homi Bhabha Road, Pune, 411 008, India. gj.sanjayan@ncl.res.in.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Copper(i)-catalyzed synthesis of 1,3-enynes via coupling between vinyl halides and alkynes or domino...
Next Document:  Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B.