Journal
CHEMICAL SCIENCE
Volume 12, Issue 24, Pages 8401-8410Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc00717c
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Funding
- North Carolina Biotechnology Center grant: NCBC [2019-IDG-1010]
- NSF [CHE-1659690]
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Hydrazones serve as a new type of submonomer in peptoid synthesis to induce structure; various hydrazones readily react with alpha-bromoamides; N-imino and N-alkylamino glycine residues favor trans-amide bond geometry formation.
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 alpha-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 corresponding N-alkylamino side chains were also identified, and both the N-imino- and N-alkylamino glycine residues were found to favor the trans-amide bond geometry by NMR, X-ray crystallography, and computational analyses.
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