4734. Homocysteine
Nomenclature
Description and references
Sulfur containing amino acid; intermediate in the biosynthesis of cysteine from methionine. Elevated serum levels have been associated with increased risk of cardiovascular disease. Readily oxidizes to the disulfide form, homocystine, q.v., or cyclizes to form the thiolactone. Produced by the demethylation of methionine: L. W. Butz, V. du Vigneaud, J. Biol. Chem. 99, 135 (1932). Prepn from S-benzylhomocysteine: B. Riegel, V. du Vigneaud, ibid. 112, 149 (1935); from cystathionine: Binkley, Methods Enzymol. 2, 314 (1955). Prepn of d- and l-forms: V. du Vigneaud, B. G. Brown, Biochem. Prep. 5, 93 (1957); H. Miyazaki et al., Bull. Chem. Soc. Jpn. 66, 536 (1993) DOI. Asymmetric synthesis of l-form: M. Adamczyk et al., Tetrahedron: Asymmetry 10, 4151 (1999) DOI. LC-ESI-MS/MS determn in plasma: S. Li et al., J. Chromatogr. B 870, 63 (2008) DOI PubMed. Review of metabolism and role in vascular disease: R. Castro et al., J. Inherit. Metab. Dis. 29, 3-20 (2006) DOI PubMed; of mechanisms of pathogenesis: J. Perla-Kaján et al., Amino Acids 32, 561-572 (2007) DOI PubMed.
