DEPBT as Coupling Reagent To Avoid Racemization in a Solution-Phase Synthesis of a Kyotorphin Derivative

Abstract

The synthesis of IbKTP-NH₂ with reduction of racemization up to no detectable level has been achieved using 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT). Among all coupling systems tested, only DEPBT-mediated amide bond formation between N^α-acylated tyrosine and arginine without loss of optical purity.

Key words

amide bond formation - coupling reagent - DEPBT - kyotorphin - racemization

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