DL-homocysteine

Also known as Hcy, 2-amino-4-sulfanyl-butanoic acid, 2-amino-4-mercapto-butyric acid, 2-amino-4-mercaptobutanoic acid, 2-amino-4-sulfanylbutanoic acid, Usaf B-12, DL-2-Amino-4-mercaptobutyric acid, (+-)-homocysteine

Homocysteine (; symbol Hcy) is a non-proteinogenic α-amino acid. It is a homologue of the amino acid cysteine, differing by an additional methylene bridge (). It is biosynthesized from methionine by the removal of its terminal Cε methyl group.

Chemical data

Formula: C4H9NO2S
Molecular weight: 135.19 g/mol
IUPAC name: 2-amino-4-sulfanylbutanoic acid
SMILES: C(CS)C(C(=O)O)N
InChIKey: FFFHZYDWPBMWHY-UHFFFAOYSA-N
XLogP: -3.4
Polar surface area: 64.3 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

186 papers

Simultaneous determination of DL-cysteine, DL-homocysteine, and glutathione in saliva and urine by UHPLC-Q-Orbitrap HRMS: Application to studies of oxidative stress.

Article

8 sections

Contents

Biosynthesis and biochemical roles
Biosynthesis of cysteine
Methionine salvage
Other reactions of biochemical significance
Homocysteine levels
Elevated homocysteine
References
External links

Although the production of homocysteine is a normal part of the metabolism of methionine, an excess of homocysteine can be harmful. There are two primary ways for organisms such as humans to metabolize homocysteine: remethylation and transsulfuration.