120610-93-7Relevant academic research and scientific papers
Studies on Amino Acids and Peptides, 13. - Improved Synthesis of 5-Thioxo-L-proline and of Some N-Acyl and S-Alkyl Derivatives as Building Blocks in Peptide Synthesis
Larsen, Claus,Kragh, Henrik,Rasmussen, Preben B.,Andersen, Torben P.,Senning, Alexander
, p. 819 - 823 (2007/10/02)
We herein report an improved synthetic pathway to 5-thioxo-L-proline (2) (using R,S nomenclature, the L form here possesses the S configuration).Compound 2 is synthesized from naturally occurring 5-oxo-L-proline (1) at room temperature with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (3) (Lawesson's reagent, LR).The synthesis is an improved version of our previously published method.The optical purity of 2 has been proven by thin-layer chromatography based on chiral ligand exchange.The synthesis of N-acyl and S-alkyl derivatives of 5-thioxo-L-proline (Top-OH), 5-thioxo-L-proline methyl ester (Top-OCH3), and the pseudodipeptide Boc-L-Phe-Top-OCH3 is also described. - Key Words: L-Proline, S-alkyl-5-thioxo-, N-acyl-5-thioxo- / Peptide building blocks / 5-Thioxo-L-proline
