Recent progress in glycochemistry and green chemistry

Citation
W. Zhang et al., Recent progress in glycochemistry and green chemistry, CURR ORG CH, 3(3), 1999, pp. 241-267
Citations number
144
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
CURRENT ORGANIC CHEMISTRY
ISSN journal
13852728 → ACNP
Volume
3
Issue
3
Year of publication
1999
Pages
241 - 267
Database
ISI
SICI code
1385-2728(199905)3:3<241:RPIGAG>2.0.ZU;2-G
Abstract
This two-part article will focus on the most recent research efforts from t he Wang's group in areas of glycochemistry and green chemistry. In the firs t part, we wish to address the progress in synthesis, conformational analys is, and transformations of some biologically active alpha-galactosyl oligos accharides. Carbohydrate structures containing Gal alpha 1-3Gal beta termin us (alpha-Gal epitopes) are xenoactive antigens and are considered to be th e major cause for hyperacute rejection in xenotransplantation. The latest c hemo-enzymatic synthesis of alpha-galactosyl epitopes using a recombinant a lpha 1,3-galactosyltransferase is described. Along with an efficient chemic al synthesis of an alpha-Gal trisaccharide, these synthetic approaches prov ide an easy access to this important class of oligosaccharides. Conformatio nal analysis of an alpha-Gal epitope using various NMR techniques and molec ular modeling is discussed. These studies provide important information in structure-function relationship and binding conformation of alpha-Gal epito pes and their interaction with anti-Gal antibody. In another aspect, novel glycoconjugates containing receptor-specific ligands and alpha-Gal epitopes have been synthesized as potential immunotherapeutic agents. The second part of this contribution summarizes our recent work in lanthani de catalysis in aqueous media. The use of Ln(OTf)(3) in organic reactions, including aza-Diels-Alder reaction, reactions of indole with aldehydes, and catalysis on solid support is discussed. An emphasis is placed on the synt hetic applications and their contribution to green technology by using envi ronmentally friendly solvents.