Thioamide bond (-CSNH-) is an isostere of the standard oxoamide bond (-CONH-).Since thioamide bond confers higher proteolytic resistance,structural rigidity,and uniquethermodynamics property on peptides,thioamides are often incorporated to natural andsynthetic molecules as well.To synthesize peptides bearing thioamides,the solid-phasesupported peptide synthesis (SPPS) has been used conventionally.The translation system,one of the most powerful tools for peptide synthesis,however,has not been used for thethioamide-bearing peptides.Although there is a single report suggesting that the ribosomecan form a thioamide bond,it was merely the dipeptide formation by means of tRNA-mimicwithout mRNA-coding.1 Therefore,no method is available to synthesize designer peptidesbearing thioamides other than SPPS to date.
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