Title of article :
Sulfatase-catalyzed assembly of regioselectively O-sulfonated p-nitrophenyl α-d-gluco- and α-d-mannopyranosides Original Research Article
Author/Authors :
Hirotaka Uzawa، نويسنده , , Yoshihiro Nishida، نويسنده , , Kenji Sasaki، نويسنده , , Takehiro Nagatsuka، نويسنده , , Hideo Hiramatsu، نويسنده , , Kazukiyo Kobayashi، نويسنده ,
Issue Information :
دوهفته نامه با شماره پیاپی سال 2004
Abstract :
A chemoenzymic methodology is extended to the library synthesis of regioselectively O-sulfonated pNP d-gluco and d-mannopyranosides. The method involves the sequential reactions of chemical O-sulfonation and sulfatase-catalyzed O-desulfonation. pNP 2,6-di-O-sulfo-α-d-glucopyranoside and pNP 3,6-di-O-sulfo-α-d-mannopyranoside were obtained as sodium salts using chemical methods by way of dibutylstannylene acetals or tributylstannyl ethers. They were then applied to enzyme reactions using three molluscan enzymes (snail, limpet, and abalone). The sulfatase reactions cleaved a sulfate group at the secondary O-2 or O-3 position to yield the corresponding pNP 6-O-sulfo sugars. Neither pNP 6-O-sulfo-α-d-glucopyranoside nor 6-O-sulfo-α-d-mannopyranoside became the enzyme substrate. Evidently, the molluscan sulfatases have a tendency to cleave the secondary O-sulfo group with assistance from the 6-O-sulfo group.
Keywords :
Regioselectivity , Library synthesis , Sulfatase , O-sulfonation
Journal title :
Carbohydrate Research
Journal title :
Carbohydrate Research