Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics

Oleg V. Kulikov; Christopher Incarvito; Andrew D. Hamilton

doi:10.1016/j.tetlet.2011.05.004

Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics

Oleg V. Kulikov, Christopher Incarvito, Andrew D. Hamilton

Chemistry

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

Abstract

A series of new alpha-helix mimetics based on a benzamide scaffold and potentially able to disrupt protein-protein interactions have been synthesized and characterized by X-ray analysis. Inspection of the solid state structures of aromatic amide dimers confirmed that the molecules adopt a curved conformation with intramolecular H-bonding between the amide NH and the alkoxy oxygen of the neighboring aromatic fragment (d_NH⋯O ∼ 2 Å). Adjacent dimer molecules are prone to form supramolecular assemblies due to both hydrophobic alkyl side-chain/side-chain interactions and intermolecular H-bonding.

Original language	English (US)
Pages (from-to)	3705-3709
Number of pages	5
Journal	Tetrahedron Letters
Volume	52
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2011.05.004
State	Published - Jul 20 2011

Keywords

Aromatic oligoamides
Helical arrangement
Hydrophobic interactions
Self-assembly

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.05.004

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title = "Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics",

abstract = "A series of new alpha-helix mimetics based on a benzamide scaffold and potentially able to disrupt protein-protein interactions have been synthesized and characterized by X-ray analysis. Inspection of the solid state structures of aromatic amide dimers confirmed that the molecules adopt a curved conformation with intramolecular H-bonding between the amide NH and the alkoxy oxygen of the neighboring aromatic fragment (dNH⋯O ∼ 2 {\AA}). Adjacent dimer molecules are prone to form supramolecular assemblies due to both hydrophobic alkyl side-chain/side-chain interactions and intermolecular H-bonding.",

keywords = "Aromatic oligoamides, Helical arrangement, Hydrophobic interactions, Self-assembly",

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note = "Funding Information: We thank the NSF (CHE-0750357) and NIH (CA67771) for partial financial support of this work. ",

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AU - Kulikov, Oleg V.

AU - Incarvito, Christopher

AU - Hamilton, Andrew D.

N1 - Funding Information: We thank the NSF (CHE-0750357) and NIH (CA67771) for partial financial support of this work.

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Y1 - 2011/7/20

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AB - A series of new alpha-helix mimetics based on a benzamide scaffold and potentially able to disrupt protein-protein interactions have been synthesized and characterized by X-ray analysis. Inspection of the solid state structures of aromatic amide dimers confirmed that the molecules adopt a curved conformation with intramolecular H-bonding between the amide NH and the alkoxy oxygen of the neighboring aromatic fragment (dNH⋯O ∼ 2 Å). Adjacent dimer molecules are prone to form supramolecular assemblies due to both hydrophobic alkyl side-chain/side-chain interactions and intermolecular H-bonding.

KW - Aromatic oligoamides

KW - Helical arrangement

KW - Hydrophobic interactions

KW - Self-assembly

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Hydrophobic side-chain interactions in a family of dimeric amide foldamers-potential alpha-helix mimetics

Abstract

Keywords

ASJC Scopus subject areas

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