Bioorthogonal techniques allow for the selective tagging of biomolecules to understand their role in a complex biological system. Our group seeks to diversify bioorthogonal tags, specifically to develop those with an allene functional group. We have synthesized two homocysteine derivatives, one containing an allene functional group (Ale) and the other containing an alkyne functional group (Myn) in moderate to good yield (39% and 71% yield, respectively). The isomerization of one to the other relies simply on pH; Myn can be converted to Ale using three molar-equivalents of NaOH under aqueous conditions. The synthesis of two tripeptides, one containing Ale (Ale-Phe-Val) and the other containing Myn (Myn-Phe-Val, 27% yield) will also be presented. We will report the optimization of the isomerization reaction of those tripeptides containing either Ale or Myn. The development of an allene-alkyne isomerization will provide a foundation for incorporation of these groups into proteins and expand their use as bioorthogonal tags.

Isomerization of allene and alkyne-containing unnatural amino acids

ACS Spring 2022

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