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Improved procedure for the synthesis of thiazolium-type peptide coupling reagents: BMTB as a new efficient reagent

✍ Scribed by Ralf Wischnat; Joachim Rudolph; Roman Hanke; Roger Kaese; Achim May; Heidi Theis; Undine Zuther

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 108 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00928-6

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✦ Synopsis

An efficient scalable synthesis of 2-halothiazolium-type peptide coupling reagents has been developed. The key step is the formation of the 2-bromothiazole scaffold through cyclization of a-thiocyanato ketones with hydrogen bromide. Using this method, the new coupling reagent 2-bromo-N-methylthiazolium bromide (BMTB) was synthesized. BMTB was tested in a difficult model coupling reaction of two sterically hindered N-methylated amino acids and showed higher activity than the well-established peptide coupling reagent HATU.

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