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

doi:10.1021/ja062710w

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

Chemistry

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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 language	English (US)
Pages (from-to)	9248-9256
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	128
Issue number	28
DOIs	https://doi.org/10.1021/ja062710w
State	Published - Jul 19 2006

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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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.",

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AU - Wang, Deyun

AU - Chen, Kang

AU - Kulp, John L.

AU - Arora, Paramjit S.

PY - 2006/7/19

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

Abstract

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