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Synfacts 2022; 18(05): 0573
DOI: 10.1055/s-0041-1737568
Peptide Chemistry

Design and Synthesis of a Thiazolium-Based Coupling Reagent for Peptide Synthesis

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
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.
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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.


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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.


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Publication History

Article published online:
20 April 2022

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