117374-86-4Relevant academic research and scientific papers
Systematic synthesis of sulfur-containing p-nitrophenyl alpha-maltopentaoside derivatives for a differential assay of human alpha-amylases.
Ozawa,Taki,Ishida,Yamagata,Satomura,Kiso,Hasegawa
, p. 821 - 828 (2007/10/02)
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.
Synthesis of p-nitrophenyl 6(5)-O-benzyl-alpha-maltopentaoside, a substrate for alpha amylases.
Satomura,Iwata,Sakata,Omichi,Ikenaka
, p. 107 - 115 (2007/10/02)
p-Nitrophenyl alpha-maltopentaoside, having a benzyl group on O-6 of the terminal (nonreducing) D-glucosyl group was prepared by use of a reductive ring-opening reaction. Highly regioselective reduction of p-nitrophenyl O-(2,3-di-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranosyl)-(1----4)- tris[O-(2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl)-(1----4)]-2,3,6-tri- O- benzoyl-alpha-D-glucopyranoside by dimethylamine-borane and p-toluenesulfonic acid, followed by debenzoylation, gave p-nitrophenyl O-(6-O-benzyl-alpha-D-glucopyranosyl)-(1----4)-tris[O-alpha-D-glucopyran osyl- (1----4)]-alpha-D-glucopyranoside. An experiment was done on the mode of action of human pancreatic and salivary alpha amylases on this derivative. The compound is suitable as a substrate for the assay of alpha amylase when used with glucoamylase and alpha-D-glucosidase as coupling enzymes.
