Design and synthesis of gentiohexaosyl derivatives for an ANP receptor antagonist, HS-142-1.
A hexaosyl fragment of the major component of lipooligosaccharide HS-142-1, O-(3-O-caproyl-beta-D-glucopyranosyl)-(1-->6)-[O-(beta-D- glucopyranosyl)-(1-->6)-O-(3-O-caproyl-beta-D-glucopyranosyl)-(1--> 6)]2-D-glucopyranose (1), was efficiently synthesized by block synthesis. More stable analogs, O-(3-O-hexyl-beta-D-glucopyranosyl)-(1-->6)-[O-(beta-D-glucopyranosyl)- (1-->6)-O-(3-O-hexyl-beta-D-glucopyranosyl)-(1-->6)]2-D-glucopyranose (4) and O-(3-O-caproyl-2,4,6-tri-O-methyl-beta-D-glucopyranosyl)-(1-->6)-[O- (2,3,4-tri-O-methyl-beta-D-glucopyranosyl)-(1-->6)-O-(3-O-caproyl-2,4-di -O- methyl-beta-D-glucopyranosyl)-(1-->6)]2-2,3,4-tri-O-methyl-D-glucopyrano se (2), were also designed and synthesized in a similar manner.
Qiu
Y
Y
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Nakahara
Y
Y
Ogawa
T
T
D002208:Caproates / Q000737:chemistry; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry; D015195:Drug Design; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000494:pharmacology*; D017461:Receptors, Atrial Natriuretic Factor / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
D002208:Caproates; D004187:Disaccharides; C072551:HS 142-1; D009844:Oligosaccharides; D011134:Polysaccharides; D017461:Receptors, Atrial Natriuretic Factor; C100052:gentiobiose