Synthetic studies on polysaccharide HS-142-1, a novel nonpeptide antagonist for the atrial natriuretic peptide receptor: syntheses of the gentiobiosyl fragments.
Possible disaccharide fragments of the major component of HS-142-1, a novel polysaccharide antagonist for functional atrial natriuretic peptide (ANP) receptors, O-(4-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-4-O-caproyl-D-glucopyranose (1) and O-(3-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-3-O-caproyl-D-glucopyranose (2), were respectively synthesized in a stereo- and regio-controlled manner. Deprotection of 2,2'-di-O-caproyl derivative 35 gave a complex mixture due to undesired acyl migration. In contrast, 2,4'-di-O-caproyl analog 39 was successfully deprotected to give O-(4-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-2-O-caproyl-D-glucopyranose (40).
Qiu
Y
Y
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Nakahara
Y
Y
Ogawa
T
T
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D017461:Receptors, Atrial Natriuretic Factor / Q000037:antagonists & inhibitors*
D004187:Disaccharides; C072551:HS 142-1; D011134:Polysaccharides; D017461:Receptors, Atrial Natriuretic Factor; C100052:gentiobiose