Conformational rearrangements by water-soluble peptoid foldamers

Sung Bin Y Shin, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

Peptoids are a family of N-substituted glycine oligomers that are capable of forming stable helical structures. We seek peptoid monomers that can establish a strong folding propensity in aqueous conditions. Here we utilize L-phenylalanine tert-butyl ester as a readily available reagent for the synthesis of (S)-N-(1-carboxy-2-phenylethyl)glycine oligomers. The products form stable secondary structures in aqueous solution in which the conformation is dramatically responsive to variations in pH and solvent composition.

Original languageEnglish (US)
Pages (from-to)5003-5006
Number of pages4
JournalOrganic Letters
Volume9
Issue number24
DOIs
StatePublished - Nov 22 2007

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Peptoids
glycine
oligomers
Oligomers
N-substituted Glycines
phenylalanine
Water
Phenylalanine
Glycine
folding
water
reagents
Conformations
esters
Esters
monomers
Monomers
aqueous solutions
synthesis
products

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Conformational rearrangements by water-soluble peptoid foldamers. / Shin, Sung Bin Y; Kirshenbaum, Kent.

In: Organic Letters, Vol. 9, No. 24, 22.11.2007, p. 5003-5006.

Research output: Contribution to journalArticle

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