Synthesis of N-modified ganglioside GM3 derivatives

Ganglioside GM3 and its derivatives have many important biological functions. Using diethyl phosphite protected sialic acid as glycosyl donor and 3,2',3',4'-unprotected lactose as glycosyl acceptor, the sialic acid-containing trisaccharide was assembled with excellent anomeric stereoselectivity. The trisaccharide was further coupled with ceramide precursor to yield sphingosine 1. Based on this key intermediate, two different series of N-modified GM3 analogues with modifications on either the nitrogen of sialic acid residue or the nitrogen of ceramide moiety and GM3 itself were synthesized smoothly. (C) 2011 Elsevier Ltd. All rights reserved.http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000299759000019&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701Chemistry, OrganicSCI(E)4ARTICLE51475-14826