title: Synthesis of 4-thia-[6-(13)C]lysine from [2- (13)C]glycine: access to site-directed isotopomers of 2-aminoethanol, 2-bromoethylamine and 4-thialysine.
abstract: 4-Thialysine (S-(2-aminoethyl)-L: -cysteine) is an analog of lysine. It has been used as an alternative substrate for lysine in enzymatic reactions. Site-directed isotopomers are often needed for elucidation of mechanism of reactions. 4-Thialysine can be synthesized by reacting cysteine with 2-bromoethylamine, an important reagent in chemical-modification rescue (CMR) of proteins. Here, we present the synthesis of 4-thia-[6-(13)C]lysine, one of the isotopomers of 4-thialysine, from commercially available starting material [2-(13)C]glycine via formation of five intermediates including 2-amino[2-(13)C]ethanol and 2-bromo[1-(13)C]ethylamine. The compounds were characterized using various spectroscopic techniques. Moreover, we discuss that our strategy would provide access to site-directed isotopomers of 2-aminoethanol, 2-bromoethylamine and 4-thialysine. Biological activity of 4-thia-[6-(13)C]lysine was tested in the enzymatic reaction of lysine 5,6-aminomutase.
authors.affiliation: Department of Physics, National Dong Hwa University, Hualien, 974-01, Taiwan.
authors.forename: Amarendra Nath
authors.initials: AN
authors.lastname: Maity
authors.forename: Ajam C
authors.initials: AC
authors.lastname: Shaikh
authors.forename: Sankareswaran
authors.initials: S
authors.lastname: Srimurugan
authors.forename: Chi-Ju
authors.initials: CJ
authors.lastname: Wu
authors.forename: Chinpiao
authors.initials: C
authors.lastname: Chen
authors.forename: Shyue-Chu
authors.initials: SC
authors.lastname: Ke
mesh_terms: D002247:Carbon Isotopes; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D019856:Ethanolamine / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D002247:Carbon Isotopes; D005021:Ethylamines; C004504:2-bromoethylamine; C000204:S-2-aminoethyl cysteine; D019856:Ethanolamine; D003545:Cysteine; D005998:Glycine