Systematic synthesis of sulfur-containing p-nitrophenyl alpha-maltopentaoside derivatives for a differential assay of human alpha-amylases.
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.
Ozawa
K
K
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Taki
Y
Y
Ishida
H
H
Yamagata
Y
Y
Satomura
S
S
Kiso
M
M
Hasegawa
A
A
D002240:Carbohydrate Sequence; D006801:Humans; D008969:Molecular Sequence Data; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000378:metabolism; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D010084:Oxidation-Reduction; D013455:Sulfur; D000516:alpha-Amylases / Q000378:metabolism*
D009578:Nitrobenzenes; D009844:Oligosaccharides; D013455:Sulfur; D000516:alpha-Amylases