Enantiospecific synthesis of pseudoacarviosin as a potential antidiabetic agent.
A pseudo-1,4'- N-linked disaccharide, pseudoacarviosin 5, was constructed via a key palladium-catalyzed coupling reaction of pseudoglycosyl chloride 8 (prepared from d-glucose via a novel direct intramolecular aldol addition in 12 steps) and pseudo-4-amino-4,6-dideoxy-alpha- d-glucose 9 (prepared from l-arabinose via an unusual trans-fused isoxazolidine-selective intramolecular nitrone-alkene cycloaddition in 11 steps). Pseudoacarviosin 5 has been shown to be a potent inhibitor of alpha-glucosidases, particularly the intestinal mucosal enzymes sucrase and glucoamylase of relevance to blood glucose control.
Shing
Tony K M
TK
Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong, China. tonyshing@cuhk.edu.hk
Cheng
Hau M
HM
Wong
Wai F
WF
Kwong
Connie S K
CS
Li
Jianmei
J
Lau
Clara B S
CB
Leung
Po Sing
PS
Cheng
Christopher H K
CH
D002384:Catalysis; D003920:Diabetes Mellitus / Q000188:drug therapy; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
D004187:Disaccharides; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; C530932:pseudoacarviosin