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

Abstract

For use in a differential assay of human α-amylases, a variety of 6⁵-S-substituted p-nitrophenyl α-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-α-D-glucopyranosyl)-(1→4)-tris[O-(2, 3, 6-tri-O-acetyl-α-D-glucopyranosyl)-(1→4)]-2, 3, 6-tri-O-acetyl-α-D-glucopyranoside (4), which was easily prepared from p-nitrophenyl α-maltopentaoside (G5P) in four steps. The sulfoxide and sulfone derivatives were prepared by oxidizing the corresponding sulfides with m-chloroperbenzoic acid.