Hydrogen Peroxide → N-Acetyl-D-Galactosamine

HRID 392671

Reaction equation

HRID 392671 reaction equation
[CH3:1][C:2]([NH:4][CH:5]1[CH:10]([OH:11])[O:9][CH:8]([CH2:12][OH:13])[CH:7]([OH:14])[CH:6]1[OH:15])=[O:3].OO.[O:18]=[CH:19][C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([CH2:28][OH:29])[OH:27])[OH:25])[OH:23])[OH:21]>>[C:2]([NH:4][C@@H:5]1[C@@H:6]([OH:15])[C@@H:7]([OH:14])[C@@H:8]([CH2:12][OH:13])[O:9][CH:10]1[OH:11])(=[O:3])[CH3:1].[O:18]=[CH:19][C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([CH2:28][OH:29])[OH:27])[OH:25])[OH:23])[OH:21]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 899N-Acetyl-HexosamineHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 2

HCID 35717N-Acetyl-D-GalactosamineHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Procedure

N-Acetylhexosamine dialdose may, for example, be manufactured by oxidation of the 6-position of N-acetylhexosamine either chemically or enzymatically. An example of the chemical oxidation is a Fenton method where oxidation is carried out with hydrogen peroxide in the presence of a ferrous salt while that of the enzymatic oxidation is an oxidation using galactose oxidase [EC 1.1.3.9; Cooper, et al.; The Journal of Biological Chemistry, volume 234, pages 445-448 (1959)]. Oxidation of N-acetyl-D-galactosamine with galactose oxidase gives N-acetylgalactosamine dialdose.

Sources & evidence

ORD record
ord-206abd35e2754908b10ae8763bb2799f
Source dataset
uspto-grants-2004_10
Patent number
US06803367B2

Linked notes

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