Methanol → beta-d-Glucopyranosylascorbic acid

HRID 505070

Reaktionsgleichung

Reaktionsgleichung von HRID 505070
CO.[C@@H]1([O:14][C:15]2[C:16]([O:18][C@H:19]([C@H:22]([CH2:24][OH:25])[OH:23])[C:20]=2[OH:21])=[O:17])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O=[C:27]1[O:33][C@H:32]([C@H:34]([CH2:36][OH:37])[OH:35])[C:30]([OH:31])=[C:28]1[OH:29]>C([O-])(=O)C.C(O)[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O>[C@@H:27]1([C@:19]2([C@H:22]([CH2:24][OH:25])[OH:23])[O:18][C:16](=[O:17])[C:15]([OH:14])=[C:20]2[OH:21])[O:33][C@H:32]([CH2:30][OH:31])[C@@H:34]([OH:35])[C@H:36]([OH:37])[C@H:28]1[OH:29]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 54670067L-Ascorbic AcidHCID 547068332-o-beta-d-Glucopyranosyl-l-ascorbic acid

Produkt 1

HCID 131727542beta-d-Glucopyranosylascorbic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 175AcetateLösungsmittelHCID 10712D-(+)-Cellobiose (CNP0226604.15)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Using, as an index, a retention time of 5.2 minutes in LC system manufactured by GILSON (master pump 305 type, UV detector 116 type), column: INERTSIL® ODS-3 (manufactured by GL Science, 4.6×150 mm, 5 μm) , mobile phase: 20% MeOH-20 mM phosphoric acid-5 mM tetra-n-amylammonium bromide, flow rate: 0.5 ml/min, detection wavelength: 254 nm) of a chemically synthesized product of 2-O-(β-D-glucopyranosyl)ascorbic acid, commercially available cellulase, (β-glucosidase, and β-glucanase enzyme preparations were searched. An enzyme reaction system was obtained by being dissolved in a 10 mM acetate buffer (pH 5.0) to 1 ml so that cellobiose became to be 0.3 M and ascorbic acid became to be 0.2 M. After addition of 50 μl of an enzyme solution, the reaction was initiated at 37° C. The reaction was stopped by heating at 100° C. for 5 minutes, and β-D-glucopyranosylascorbic acid produced was analyzed by high performance liquid chromatography. As a result, it was found that cellulase (manufactured by Sigma), β-glucosidase (Toyobo Co., Ltd., Nakarai Tesque), CELLULOSIN T2 (Hankyu Kyoei Bussan), cellulase “ONOZUKA” RS, “ONOZUKA” FA and PANCELLASE BR (Yakult Pharmaceutical Ind. Co., Ltd.) have (β-glucosyltransferase activity. Free ascorbic acid appeared a position of 4.0 minutes, while peaks were recognized at positions of 3.6 minutes and 5.2 minutes before and after that position, and they were designated as substance X and substance Y. A conversion rate of the substance X indicated 15.7%, and a conversion rate of the substance Y indicated 0.8%. By cochromatography analysis of this substance X and substance Y with chemically synthesized products, a retention time of the substance X was consistent with that of 6-O-(β-D-glucopyranosyl)ascorbic acid, and a retention time of the substance Y was consistent with that of 2-O-(β-D-glucopyranosyl)ascorbic acid.

Aufarbeitung

  1. customAn enzyme reaction system was obtained
  2. customwas initiated at 37° C

Quellen und Nachweise

ORD-Eintrag
ord-899ec73c740e457eac004330e3ff1bdc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781409B2

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