Submonomer synthesis of peptoids containingtrans-inducingN-imino- andN-alkylamino-glycines

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Abstract

The use of hydrazones as a new type of submonomer in peptoid synthesis is described, giving access to peptoid monomers that are structure-inducing. A wide range of hydrazones were found to readily react with α-bromoamides in routine solid phase peptoid submonomer synthesis. Conditions to promote a one-pot cleavage of the peptoid from the resin and reduction to the correspondingN-alkylamino side chains were also identified, and both theN-imino- andN-alkylamino glycine residues were found to favor thetrans-amide bond geometry by NMR, X-ray crystallography, and computational analyses.

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Davern, C. M., Lowe, B. D., Rosfi, A., Ison, E. A., & Proulx, C. (2021). Submonomer synthesis of peptoids containingtrans-inducingN-imino- andN-alkylamino-glycines. Chemical Science, 12(24), 8401–8410. https://doi.org/10.1039/d1sc00717c

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