Systematic Synthesis of Sulfur-containingp-Nitrophenyl α-Maltopentaoside Derivatives for a Differential Assay of Human α-Amylases

Abstract

For use in a differential assay of human alpha-amylases, a variety of 6(5)-S-substituted p-nitrophenyl alpha-maltopentaoside derivatives (6-54) were systematically synthesized via the key intermediate, p-nitrophenyl O-(2,3-di-O-acetyl-6-S-acetyl-4-O-benzoyl-6-thio-alpha-D-glucopyranosyl) - (-->4)-tris[O-(2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl)-(1-->4)]-2,3,6 -tri-O-acetyl-alpha-D-glucopyranoside (4), which was easily prepared from p-nitrophenyl alpha-maltopentaoside (G5P) in four steps. The sulfoxide and sulfone derivatives were prepared by oxidizing the corresponding sulfides with m-chloroperbenzoic acid.