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Improved procedure for the synthesis of thiazolium-type peptide coupling reagents: BMTB as a new efficient reagent |
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| Authors: | Ralf Wischnat Joachim RudolphRoman Hanke Roger KaeseAchim May Heidi TheisUndine Zuther |
| Institution: | a Bayer AG, Pharma Operations PH-OP-WP, Friedrich Ebert Str. 217, D-42096, Germany b Department of Chemistry Research, Bayer Corporation, Pharmaceutical Division, 400 Morgan Lane, West Haven, CT 06516, USA c Bayer AG, Central Research, Building Q18, D-51368 Leverkusen, Germany |
| Abstract: | 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 α-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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