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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.

SUBMITTER: Davern CM

PROVIDER: S-EPMC8221195 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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

Davern Carolynn M CM Lowe Brandon D BD Rosfi Adam A Ison Elon A EA Proulx Caroline C

Chemical science 20210510 24

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 resi ...[more]

PMID: 34221321

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