Synthesis of "dihydroacarbose", an alpha-D-glucosidase inhibitor having a pseudo-tetrasaccharide structure.
"Dihydroacarbose" (2), an alpha-D-glucosidase inhibitor having a pseudo-tetrasaccharide structure, was synthesized by reductive coupling of 4(3)-amino-1(1),6(1)-anhydro-2(1),3(1),2(2),3(2),6(2),2(3),3(3)-hepta-O- benzyl-4(3),6(3)-dideoxy-beta-maltotriose and 2D-(2,4/3,5)-2,3,4-tris(benzyloxy)-5-(trityloxymethyl)cyclohexa non e with sodium-cyanoborohydride. The former intermediate was prepared from a partially benzylated 1(1),6(1)-anhydro-beta-maltotriose, and the latter was prepared from a chiral, penta-substituted cyclohexene derived from D-glucose. The synthetic 2 was found to be a strong, non-competitive inhibitor (Ki = 1.13 x 10(-6) M) against small-intestinal sucrase of rat.
Hayashida
M
M
RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan.
Sakairi
N
N
Kuzuhara
H
H
Yajima
M
M
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D065089:Glycoside Hydrolase Inhibitors; D007202:Indicators and Reagents; D007421:Intestine, Small / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D009904:Optical Rotation; D051381:Rats; D011919:Rats, Inbred Strains; D013055:Spectrophotometry, Infrared; D013393:Sucrase / Q000037:antagonists & inhibitors*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology
D065089:Glycoside Hydrolase Inhibitors; D007202:Indicators and Reagents; D009844:Oligosaccharides; D014312:Trisaccharides; C052108:dihydroacarbose; D013393:Sucrase