Hydrogen Peroxide → 3-(allylsulphinyl)-L-alanine

HRID 2120047

Reaction equation

[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[CH2:8](Br)[CH:9]=[CH2:10].[OH:12]O>>[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]([CH2:8][CH:9]=[CH2:10])=[O:12]

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 5862L-(+)-Cysteine

HCID 7841Allyl bromide

Product 1

HCID 873103-(allylsulphinyl)-L-alanineYield 15.7%

Procedure

Alliin was synthesized from L-cysteine and allyl bromide following oxidation by H2O2 by the procedure of Stoll and Seebeck, 1951. The stereospecific product obtained, (+)S-allyl-L-cysteine sulfoxide (M.P.=164°, [α]D in H2O+62.1°), was identical to the natural substrate, alliin (Yield: 15.7%).

Workup

customThe stereospecific product obtained

Sources & evidence

ORD record: ord-cab322929182430ea80d8cd7f54e6635
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689588B1

Linked notes

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