Enzymatic synthesis of N-acetylglucosaminyl-cyclodextrin by the reverse reaction of N-acetylhexosaminidase from jack bean.
Novel heterobranched cyclodextrins (CDs), N-acetylglucosaminyl-cyclodextrins (GlcNAc-CD), were synthesized from a mixture of GlcNAc and alpha, beta, or gamma CD by the reverse reaction of N-acetylhexosaminidase from jack bean. Optimum pH and temperature for the production of GlcNAc-alpha CD by N-acetylhexosaminidase were pH 4.9 and 50-70 degrees C, respectively. The maximum yield of GlcNAc-alpha CD was 17.5% (mol/mol) at the concentration of 1 M GlcNAc and 0.25 M alpha CD. The reverse reaction product, GlcNAc-alpha CD, was separated into two peaks by HPLC analysis on the ODS column. Their structures were identified as 6-O-beta-D-N-acetylglucosaminyl-alpha CD and 2-O-beta-D-N-acetylglucosaminyl-alpha CD by FAB-MS and NMR spectroscopies. N-Acetylhexosaminidase from jack bean also synthesized N-acetylgalactosaminyl-alpha CD from N-acetylgalactosamine and alpha CD.
Hamayasu
K
K
Bio Research Corporation of Yokohama, Japan. QZA01063@nifty.ne.jp
Fujita
K
K
Hara
K
K
Hashimoto
H
H
Tanimoto
T
T
Koizumi
K
K
Nakano
H
H
Kitahata
S
S
D002845:Chromatography / Q000379:methods; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D004337:Drug Carriers / Q000138:chemical synthesis; D007887:Fabaceae / Q000201:enzymology*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal; D013696:Temperature; D013997:Time Factors; D047391:alpha-Cyclodextrins; D001619:beta-N-Acetylhexosaminidases / Q000737:chemistry* / Q000378:metabolism*
C403302:2-O-(N-acetylglucosaminyl)-alpha-cyclodextrin; D003505:Cyclodextrins; D004337:Drug Carriers; D047391:alpha-Cyclodextrins; D001619:beta-N-Acetylhexosaminidases