Synthetic Studies on Polysaccharide HS-142-1, a Novel Nonpeptide Antagonist for the Atrial Natriuretic Peptide Receptor: Syntheses of the Gentiobiosyl Fragments

Abstract

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-β-D-glucopyranosyl)-(1→6)-4-O-caproyl-D-glucopyranose (1) and O-(3-O-caproyl-β-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-β-D-glucopyranosyl)-(1→6)-2-O-caproyl-D-glucopyranose (40).