36017-44-4Relevant academic research and scientific papers
Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
Chen, Yu,Su, Li,Yang, Xinying,Pan, Wenyan,Fang, Hao
, p. 9234 - 9239 (2015/11/27)
A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.
A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines
Chen, Wenteng,Shao, Jiaan,Hu, Miao,Yu, Wanwan,Giulianotti, Marc A.,Houghten, Richard A.,Yu, Yongping
, p. 970 - 976 (2013/06/05)
A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.
