Ishiwata A,
Ichiyanagi T,
Takatani M,
Ito Y.
*
RIKEN (The Institute of Physical and Chemical Research), Wakō, Japan
Chemoselective Peptide Bond Formation Using Formyl-Substituted Nitrophenylthio Ester.
Tetrahedron Lett. 2003;
44: 3187-3190
DOI:
10.1016/s0040-4039(03)00471-4
Key words
dipeptides - formyl nitrophenyl thio esters - methylmaleimide - 1,4-addition - chemoselectivity
Significance
Amide bond formation is very significant in peptide chemistry, and many approaches have been developed to form the peptide bonds. The authors used formyl-substituted S-4-nitrophenyl thioesters to synthesize dipeptides. The reaction could be conducted in the presence of water.
Comment
A broad variety of dipeptides can be synthesized from S-2-formyl-4-nitrophenyl thioesters and amino acid salts. N-Methylmaleimide is used to trap the resulting thiophenol to improve the final yield. The yields of the reactions are good to excellent.
