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reaction mixture containing 1.55
1-phosphate, and 50 mM suitable acceptor (
l
M ACL0729, 50 mM
-glucose, 2-deoxy-
-glucuronic acid, 1,5-anhydro- -glucitol, and
-mannose) in a final volume of 500 L of 10 mM MES-NaOH (pH
-glucose, -xylose,
-mannose were used as the acceptors,
a-D-glucose
D
D-glucose,
D
-xylose,
D
D
D
l
6.0) incubated at 30 °C for 70 h. In cases where
D
D
1,5-anhydro- -glucitol, and
D
D
the reaction mixtures were desalted using Amberlite MB-3
(Organo, Tokyo, Japan), and the products were purified by a high
performance liquid chromatography system (Prominence, Shima-
dzu, Kyoto, Japan) equipped with a Shodex Asahipak NH2P-50 4E
column (4.6 mm
at 30 °C under a constant flow (1.0 mL/min) of mobile phase
(acetonitrile/water v/v, 75/25). In cases of 2-deoxy- -glucose and
-glucuronic acid as the acceptors, the reaction mixtures were neu-
tralized by addition of 1 M NaOH and treated with a recombinant
-glucose 1-phosphatase from E. coli46 at 30 °C for 12 h, and
the products were separated on a Toyopearl HW-40S column
(26 mm
u
ꢂ 250 mm; Showa Denko K.K., Tokyo, Japan)
D
D
a-D
u
ꢂ 650 mm; TOSOH, Tokyo, Japan) equilibrated with dis-
tilled water at a flow rate of 0.5 mL/min. Fractions containing the
reaction products were collected, followed by lyophilization. The
amounts of products obtained were 5.5, 4.9, 5.9 (4.9 mg of main
product and 1.0 mg of by-product), 4.0, 5.0, and 6.0 mg from
cose, 2-deoxy- -glucose, -xylose, -glucuronic acid, 1,5-anhydro-
-glucitol, and -mannose as the acceptor, respectively. The
D-glu-
D
D
D
D
D
one-dimensional (1H and 13C) and two-dimensional [double-quan-
tum-filtered correlation spectroscopy (DQF-COSY), heteronuclear
single-quantum coherence (HSQC), and heteronuclear multiple-
bond correlation (HMBC)] nuclear magnetic resonance (NMR)
spectra of the product were taken in D2O with 2-methyl-2-propa-
nol as an internal standard using Bruker Avance 500 or Bruker
Avance 800 spectrometer (Bruker Biospin, Rheinstetten, Germany).
Proton signals were assigned based on DQF-COSY spectra. 13C sig-
nals were assigned with HSQC spectra, based on the assignment of
proton signals. The linkage position in each disaccharide was
determined by detecting inter-ring cross peaks in each HMBC
spectrum.
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Acknowledgments
We thank the staffs of Instrumental Analysis Center for Food
Chemistry of National Food Research Institute for recording NMR
spectra. This work was supported in part by MEXT’s program ‘Pro-
motion of Environmental Improvement for Independence of Young
Researchers’ under the Special Coordination Funds for Promoting
Science and Technology.
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Supplementary data
Supplementary data associated with this article can be found, in
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