Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix

Johanna M. Rodriguez; Andrew D. Hamilton

doi:10.1016/j.tetlet.2006.08.048

Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix

Johanna M. Rodriguez, Andrew D. Hamilton

Chemistry

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

Abstract

An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.

Original language	English (US)
Pages (from-to)	7443-7446
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2006.08.048
State	Published - Oct 16 2006

Keywords

Enaminone
Hydrogen bonding
α-Helix mimetic

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.08.048

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abstract = "An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.",

keywords = "Enaminone, Hydrogen bonding, α-Helix mimetic",

author = "Rodriguez, {Johanna M.} and Hamilton, {Andrew D.}",

note = "Funding Information: We thank the National Institutes of Health (GM69850) for financial support of this work. ",

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AU - Rodriguez, Johanna M.

AU - Hamilton, Andrew D.

N1 - Funding Information: We thank the National Institutes of Health (GM69850) for financial support of this work.

PY - 2006/10/16

Y1 - 2006/10/16

N2 - An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.

AB - An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.

KW - Enaminone

KW - Hydrogen bonding

KW - α-Helix mimetic

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix

Abstract

Keywords

ASJC Scopus subject areas

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