Evaluation of Biologically Relevant Short -Helices Stabilized by a Main-Chain Hydrogen-Bond Surrogate

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• 作者：Deyun Wang ; Kang Chen ; John L. Kulp III ; and Paramjit S. Arora
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：July 19, 2006
• 年：2006
• 卷：128
• 期：28
• 页码：9248 - 9256
• 全文大小：759K
• 年卷期：v.128,no.28(July 19, 2006)
• ISSN：1520-5126

文摘

We previously reported the design and synthesis of a new class of artificial -helices in whichan N-terminal main-chain hydrogen bond is replaced by a carbon-carbon bond derived from a ring-closingmetathesis 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 potentialof this method for the synthesis of very short (10 residues) -helices representing two different biologicallyrelevant -helical domains. We extensively characterized these two sets of artificial helices by NMR andcircular dichroism spectroscopies and find that the hydrogen-bond surrogate approach can afford well-defined short -helical structures from sequences that do not spontaneously form -helical conformations.