Issue 24, 2021

Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines

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 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.

Graphical abstract: Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Feb 2021
Accepted
09 May 2021
First published
10 May 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 8401-8410

Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines

C. M. Davern, B. D. Lowe, A. Rosfi, E. A. Ison and C. Proulx, Chem. Sci., 2021, 12, 8401 DOI: 10.1039/D1SC00717C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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