Synthesis of monomethyl derivatives of p-nitrophenyl α-d-gluco, galacto, and mannopyranosides and their hydrolytic properties against α-glycosidases

Article abstract of DOI:10.1080/07328300008544084

All possible monomethyl derivatives of p-nitrophenyl α-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of α-glucosidase (rice), α-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and α-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea α-galactosidase and the almond and jack bean α-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, rice α-glucosidase and green coffee bean and A. niger α-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

Full text of DOI:10.1080/07328300008544084

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Journal of Carbohydrate Chemistry
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Synthesis of Monomethyl Derivatives
of P-Nitrophenyl α-D-Gluco, Galacto,
and Mannopyranosides and their
Hydrolytic Properties Against α-
Glycosidases
Wataru Hakamata , Toshiyuki Nishio , Reiko Sato , Takahiro
Mochizuki , Kazuya Tsuchiya , Maki Yasuda & Tadatake Oku
a Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
b Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
c Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
d Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
e Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
f Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
g Laboratory of Bio-organic Chemistry, College of Bioresource
Sciences, Nihon University, 3-34-1, Shimouma, Setagaya-ku
Tokyo 154-8513, Japan E-mail:
Version of record first published: 27 Feb 2008.
To cite this article: Wataru Hakamata , Toshiyuki Nishio , Reiko Sato , Takahiro Mochizuki ,
Kazuya Tsuchiya , Maki Yasuda & Tadatake Oku (2000): Synthesis of Monomethyl Derivatives
of P-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties
Against α-Glycosidases, Journal of Carbohydrate Chemistry, 19:3, 359-377

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