Synthesis of 4-thia-[6-13C]lysine from [2-13C]glycine: access to site-directed isotopomers of 2-aminoethanol, 2-bromoethylamine and 4-thialysine |
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Authors: | Amarendra Nath Maity Ajam C. Shaikh Sankareswaran Srimurugan Chi-Ju Wu Chinpiao Chen Shyue-Chu Ke |
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Affiliation: | (1) Department of Physics, National Dong Hwa University, Hualien, 974-01, Taiwan;(2) Department of Chemistry, National Dong Hwa University, Hualien, 974-01, Taiwan; |
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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-[6-13C]lysine, one of the isotopomers of 4-thialysine, from commercially available starting material [2-13C]glycine via formation of five intermediates including 2-amino[2-13C]ethanol and 2-bromo[1-13C]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-[6-13C]lysine was tested in the enzymatic reaction of lysine 5,6-aminomutase. |
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