Li P,
Xu JC.
*
Shanghai Institute of Organic Chemistry, P. R. of China
A Novel Thiazolium Type Peptide Coupling Reagent for Hindered Amino Acids.
Tetrahedron Lett. 1999;
40: 8301-8304
DOI:
10.1016/S0040-4039(99)01763-3
Key words
bromoethylmethyl-thiazolium tetrafluoroborate - amino acids - coupling reagent
Significance
The development of efficient and novel coupling reagents for peptide-bond formation
is the backbone of the peptide industry and has attracted extreme attention for the
last three decades. In 1999, Xu and Li developed an efficient thiazolium-type peptide
coupling agent for the synthesis of peptides containing N-allyl amino acid residues.
Comment
2-Bromo-3-ethyl-4-methylthiazolium tetrafluoroborate (BEMT) is an efficient coupling
agent for the synthesis of oligopeptides bearing N-alkyl or α-C-dialkyl amino acids. This coupling agent can produce a series of hindered peptides
in high yields with negligible racemization. The mechanism of the coupling reaction
was studied with the help of NMR, HPLC, and IR spectroscopy.
