Racemization-Free Ynamide-Type Condensing Agent

MYTsA (1) is a thermally-stable condensing agent developed by Zhao et al. and is usable in water solution for amide/peptide synthesis.^1,2) 1 has several advantages over conventional condensing agents; racemization seldom occurs even in cases of substrates in which racemization tends to occur; the reaction proceeds preferentially at the amino group in the presence of an unprotected hydroxy group, thiol group, primary amide (-CONH₂) and 1-NH moiety of indole. In addition, 1 is applicable in sterically-hindered substrates such as 2-aminoisobutyric acid and valine derivatives to give the amides in high yields.

References

• 1) Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis
  • L. Hu, S. Xu, Z. Zhao, Y. Yang, Z. Peng, M. Yang, C. Wang, J. Zhao, J. Am. Chem. Soc. 2016, 138, 13135.
• 2) A computational study on the mechanism of ynamide-mediated amide bond formation from carboxylic acids and amines
  • S.-L. Zhang, H.-X. Xing, Z.-Q. Deng, Org. Biomol. Chem. 2017, 15, 6367.

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