title: Regioselective one-pot protection and protection-glycosylation of carbohydrates.
abstract: Deciphering the roles and structure-activity relationships of carbohydrates in biological processes requires access to sugar molecules of confirmed structure and high purity. Chemical synthesis is one of the best ways to obtain such access. However, the synthesis of carbohydrates has long been impeded by two major challenges--the regioselective protection of the polyol moiety of each monosaccharide building block and the stereoselective glycosylation to produce oligosaccharides of desired length. Here, we review the development of the first regioselective protection-glycosylation and a revolutionary regioselective combinatorial one-pot protection of monosaccharides that can be used to differentiate the various hydroxy groups of monosaccharides with a vast array of orthogonal protective groups in one-pot procedures.
authors.affiliation: Institute of Chemistry, Academia Sinica 128, Section 2, Academia Road, Taipei, Taiwan. wangcc@chem.sinica.edu.tw
authors.forename: Cheng-Chung
authors.initials: CC
authors.lastname: Wang
authors.forename: Medel Manuel L
authors.initials: MM
authors.lastname: Zulueta
authors.forename: Shang-Cheng
authors.initials: SC
authors.lastname: Hung
mesh_terms: D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates