Design and synthesis of oligoamide-based double α-helix mimetics

Oleg V. Kulikov; Sam Thompson; Hai Xu; Christopher D. Incarvito; Richard T.W. Scott; Ishu Saraogi; Laura Nevola; Andrew D. Hamilton

doi:10.1002/ejoc.201300363

Design and synthesis of oligoamide-based double α-helix mimetics

Oleg V. Kulikov, Sam Thompson, Hai Xu, Christopher D. Incarvito, Richard T.W. Scott, Ishu Saraogi, Laura Nevola, Andrew D. Hamilton

Chemistry

Research output: Contribution to journal › Article › peer-review

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 α-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.

Original language	English (US)
Pages (from-to)	3433-3445
Number of pages	13
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201300363
State	Published - Jun 2013

Keywords

Amides
Helical structures
Hydrogen bonds
Peptidomimetics
Synthesis design

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201300363

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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 α-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.",

keywords = "Amides, Helical structures, Hydrogen bonds, Peptidomimetics, Synthesis design",

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AU - Xu, Hai

AU - Incarvito, Christopher D.

AU - Scott, Richard T.W.

AU - Saraogi, Ishu

AU - Nevola, Laura

AU - Hamilton, Andrew D.

PY - 2013/6

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AB - 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 α-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.

KW - Amides

KW - Helical structures

KW - Hydrogen bonds

KW - Peptidomimetics

KW - Synthesis design

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Design and synthesis of oligoamide-based double α-helix mimetics

Abstract

Keywords

ASJC Scopus subject areas

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