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Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics

Kulikov, Oleg V. and Thompson, Sam and Xu, Hai and Incarvito, Christopher D. and Scott, Richard T. W. and Saraogi, Ishu and Nevola, Laura and Hamilton, Andrew D. (2013) Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics. European Journal of Organic Chemistry, 2013 (17). pp. 3433-3445. ISSN 1434-193X. https://resolver.caltech.edu/CaltechAUTHORS:20130712-102051387

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Abstract

An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double -helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ejoc.201300363DOIUNSPECIFIED
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300363/abstractPublisherUNSPECIFIED
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: March 10, 2013; published Online: May 23, 2013. The authors thank the National Science Foundation (NSF) (CHE-0750357), National Institutes of Health (NIH) (CA67771) and the University of Oxford, UK for funding.
Funders:
Funding AgencyGrant Number
NSFCHE-0750357
NIHCA67771
University of OxfordUNSPECIFIED
Subject Keywords:Synthesis design; Amides; Peptidomimetics; Hydrogen bonds; Helical structures
Issue or Number:17
Record Number:CaltechAUTHORS:20130712-102051387
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130712-102051387
Official Citation:Kulikov, O. V., Thompson, S., Xu, H., Incarvito, C. D., Scott, R. T. W., Saraogi, I., Nevola, L. and Hamilton, A. D. (2013), Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics. Eur. J. Org. Chem., 2013: 3433–3445. doi: 10.1002/ejoc.201300363
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39336
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:15 Jul 2013 14:38
Last Modified:03 Oct 2019 05:06

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