Formaldehyde → Methylglyoxal

HRID 1288662Notes

Reaction equation

HRID 1288662 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4].C=O.C(C(/C=C\C(O)=O)=O)C(CC(O)=O)=[O:25].ClC(Cl)(Cl)C(C1C=CC(Cl)=CC=1)C1C=CC(Cl)=CC=1>>[CH3:6][C:2]([CH:3]=[O:5])=[O:25].[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 30361-Chloro-4-(2,2,2-trichloro-1-(4-chlorophenyl)ethyl)benzeneHCID 124886GlutathioneHCID 52803934-Maleylacetoacetic acid

Product 2

HCID 880MethylglyoxalHCID 124886Glutathione

Procedure

Glutathione functions as a co-enzyme for formaldehyde dehydrogenase, maleylacetoacetate isomerase, glyoxalase, prostaglandin endoperoxidase isomerases, and dichlorodiphenyltrichloroethane dehydrochlorinase and similar enzymes. In the glyoxalase reaction, the hemimercaptal formed nonenzymatically by reaction of methylglyoxal and glutathione (GSH) is converted by glyoxalase I to S-lactyl-Glutathione, which is split by glyoxalase II to D-lactate and Glutathione. In the formaldehyde dehydrogenase reaction, S-formyl Glutathione is formed (Glutathione+HCHO+NAD+) and hydrolyzed to formate and Glutathione.

Workup

  1. customIn the glyoxalase reaction

Sources & evidence

ORD record
ord-20f240749d8c4433b23b4769c315dad3
Source dataset
uspto-grants-1998_05
Patent number
US05747329

Reaction notes

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