Double-sided α-helix mimetics

Sam Thompson; Ramakrishnan Vallinayagam; Marc J. Adler; Richard T.W. Scott; Andrew D. Hamilton

doi:10.1016/j.tet.2011.11.010

Double-sided α-helix mimetics

Sam Thompson, Ramakrishnan Vallinayagam, Marc J. Adler, Richard T.W. Scott, Andrew D. Hamilton

Chemistry

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

Abstract

The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an α-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.

Original language	English (US)
Pages (from-to)	4501-4505
Number of pages	5
Journal	Tetrahedron
Volume	68
Issue number	23
DOIs	https://doi.org/10.1016/j.tet.2011.11.010
State	Published - Jun 10 2012

Keywords

Foldamer
Helical structure
Peptidomimetic
Protein-protein interaction
Proteomimetic

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.11.010

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title = "Double-sided α-helix mimetics",

abstract = "The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an α-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.",

keywords = "Foldamer, Helical structure, Peptidomimetic, Protein-protein interaction, Proteomimetic",

author = "Sam Thompson and Ramakrishnan Vallinayagam and Adler, {Marc J.} and Scott, {Richard T.W.} and Hamilton, {Andrew D.}",

note = "Funding Information: We thank Dr. Martin D. Smith (Oxford) for helpful discussions and The University of Oxford for funding (S.T.).",

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T1 - Double-sided α-helix mimetics

AU - Thompson, Sam

AU - Vallinayagam, Ramakrishnan

AU - Adler, Marc J.

AU - Scott, Richard T.W.

AU - Hamilton, Andrew D.

N1 - Funding Information: We thank Dr. Martin D. Smith (Oxford) for helpful discussions and The University of Oxford for funding (S.T.).

PY - 2012/6/10

Y1 - 2012/6/10

N2 - The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an α-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.

AB - The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an α-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.

KW - Foldamer

KW - Helical structure

KW - Peptidomimetic

KW - Protein-protein interaction

KW - Proteomimetic

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DO - 10.1016/j.tet.2011.11.010

M3 - Article

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VL - 68

SP - 4501

EP - 4505

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Double-sided α-helix mimetics

Abstract

Keywords

ASJC Scopus subject areas

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