Evaluation of biologically relevant short α-helices stabilized by a main-chain hydrogen-bond surrogate

Deyun Wang, Kang Chen, John L. Kulp, Paramjit S. Arora

Research output: Contribution to journalArticlepeer-review

Abstract

We previously reported the design and synthesis of a new class of artificial α-helices in which an N-terminal main-chain hydrogen bond is replaced by a carbon-carbon bond derived from a ring-closing metathesis reaction [Chapman, R. N.; Dimartino, G.; Arora, P. S. J. Am. Chem. Soc. 2004, 126, 12252-12253]. Our initial study utilized an alanine-rich sequence; in the present manuscript we evaluate the potential of this method for the synthesis of very short (10 residues) α-helices representing two different biologically relevant α-helical domains. We extensively characterized these two sets of artificial helices by NMR and circular dichroism spectroscopies and find that the hydrogen-bond surrogate approach can afford well-defined short α-helical structures from sequences that do not spontaneously form α-helical conformations.

Original languageEnglish (US)
Pages (from-to)9248-9256
Number of pages9
JournalJournal of the American Chemical Society
Volume128
Issue number28
DOIs
StatePublished - Jul 19 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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