ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

EFFICIENT SYNTHESIS OF O-LINKED GLYCOCONJUGATES OF AMINO ACIDS FROM CARBOHYDRATE-DERIVED DONOR-ACCEPTOR CYCLOPROPANES

Kishore, Gade and Gautam, Vibha and Haveli, Shrutisagar Dattatraya and Chandrasekaran, Srinivasan (2019) EFFICIENT SYNTHESIS OF O-LINKED GLYCOCONJUGATES OF AMINO ACIDS FROM CARBOHYDRATE-DERIVED DONOR-ACCEPTOR CYCLOPROPANES. In: HETEROCYCLES, 99 (1). pp. 200-212.

Full text not available from this repository.
Official URL: https://dx.doi.org/10.3987/COM-18-S(F)9

Abstract

N-Iodosuccinimide (NIS) mediated ring opening of carbohydrate-derived donor-acceptor cyclopropanes with free ``CO2H'' group of N-protected L-amino acids at ambient conditions afforded iodo derivatives of glycosyl ester of L-amino acids. The iodides were subsequently converted easily into corresponding azides using NaN3 in DMF followed by reduction with Zn/AcOH to produce ester linked glycosyl amino acids. A similar strategy was adopted to synthesize C-linked glycoamino acid derivatives from different N-protected L-amino alcohols. By using an orthogonal strategy C- and O-linked glycopeptides were also synthesized.

Item Type: Journal Article
Publication: HETEROCYCLES
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Additional Information: Copyright of this article belongs to PERGAMON-ELSEVIER SCIENCE LTD
Keywords: BUILDING-BLOCKS; GLYCOPEPTIDES; DESIGN; ESTERS; SUGAR
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 12 Feb 2020 11:33
Last Modified: 12 Feb 2020 11:33
URI: http://eprints.iisc.ac.in/id/eprint/63339

Actions (login required)

View Item View Item