2021 article

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

Davern, C. M., Lowe, B. D., Rosfi, A., Ison, E. A., & Proulx, C. (2021, May 10). CHEMICAL SCIENCE.

By: C. Davern n, B. Lowe n, A. Rosfi n, E. Ison n  & C. Proulx n 

co-author countries: United States of America πŸ‡ΊπŸ‡Έ
Source: Web Of Science
Added: June 10, 2021

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 Ξ±-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.