TY - JOUR
T1 - Efficient method for the elongation of the N-acetylglucosamine unit by combined use of chitinase and β-galactosidase
AU - Shoda, Shin ichiro
AU - Fujita, Masaya
AU - Lohavisavapanichi, Chakapan
AU - Misawa, Yoshinori
AU - Ushizaki, Koushin
AU - Tawata, Yukiko
AU - Kuriyama, Mao
AU - Kohri, Michinari
AU - Kuwata, Hideyuki
AU - Watanabe, Takeshi
PY - 2002/12/1
Y1 - 2002/12/1
N2 - A novel strategy for the regio- and stereoselective synthesis by two enzymatic steps of oligosaccharides having an N-acetylglucosamine unit at the nonreducing end was developed. The first step involves a chitinase-catalyzed highly selective β-N-acetyllactosamination of an oligosaccharide acceptor with a 4,5-dihydrooxazole derivative of N-acetyllactosamine as the glycosyl donor. The usage of a transition-state-analogue substrate for the chitinase under basic conditions allows the reaction to proceed only in the synthetic direction while suppressing hydrolysis of the product in aqueous media. Several chitinase mutants also catalyzed the glycosylation efficiently under neutral conditions, The second step is a regioselective cleavage of the glycosidic bond between the terminal galactose unit and the adjacent N-acetylglucosamine unit by the action of a β- galactosidase. This constitutes a very useful method to add an N-acetylglucosamine unit to the nonreducing end of chito- and cello-oligosaccharide derivatives in a regio- and stereoselective manner.
AB - A novel strategy for the regio- and stereoselective synthesis by two enzymatic steps of oligosaccharides having an N-acetylglucosamine unit at the nonreducing end was developed. The first step involves a chitinase-catalyzed highly selective β-N-acetyllactosamination of an oligosaccharide acceptor with a 4,5-dihydrooxazole derivative of N-acetyllactosamine as the glycosyl donor. The usage of a transition-state-analogue substrate for the chitinase under basic conditions allows the reaction to proceed only in the synthetic direction while suppressing hydrolysis of the product in aqueous media. Several chitinase mutants also catalyzed the glycosylation efficiently under neutral conditions, The second step is a regioselective cleavage of the glycosidic bond between the terminal galactose unit and the adjacent N-acetylglucosamine unit by the action of a β- galactosidase. This constitutes a very useful method to add an N-acetylglucosamine unit to the nonreducing end of chito- and cello-oligosaccharide derivatives in a regio- and stereoselective manner.
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U2 - 10.1002/1522-2675(200211)85:11<3919::AID-HLCA3919>3.0.CO;2-P
DO - 10.1002/1522-2675(200211)85:11<3919::AID-HLCA3919>3.0.CO;2-P
M3 - Article
AN - SCOPUS:0036935764
VL - 85
SP - 3919
EP - 3936
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
SN - 0018-019X
IS - 11
ER -