Evaluation of Biologically Relevant Short α-Helices Stabilized by a Main-Chain Hydrogen-Bond Surrogate
- 27 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (28) , 9248-9256
- https://doi.org/10.1021/ja062710w
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.Keywords
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