Novel amphiphilic α-helix mimetics based on a bis-benzamide scaffold

Srinivasa Marimgantl, Murthy N. Cheemala, Jung Mo Ahn

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

To mimic amphophilic a-helices, a new scaffold was designed based on a bis-benzamide that places four side-chain functional groups found at the i, i+2, i+5, and i+7 positions of a helix. Its two hydrogen bonds fix the conformation and provide accurate bifacial arrangement of the four substituents, simultaneously representing two opposing helical sides. An efficient synthetic route was achieved for the construction of bis-benzamides, and their superior a-helix mimicry was confirmed by X-ray crystallography.

Original languageEnglish (US)
Pages (from-to)4418-4421
Number of pages4
JournalOrganic Letters
Volume11
Issue number19
DOIs
StatePublished - Oct 1 2009

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Benzamides
X ray crystallography
X Ray Crystallography
Scaffolds
helices
Functional groups
Conformations
Hydrogen
Hydrogen bonds
fixing
crystallography
routes
hydrogen bonds
benzamide
x rays

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Novel amphiphilic α-helix mimetics based on a bis-benzamide scaffold. / Marimgantl, Srinivasa; Cheemala, Murthy N.; Ahn, Jung Mo.

In: Organic Letters, Vol. 11, No. 19, 01.10.2009, p. 4418-4421.

Research output: Contribution to journalArticle

Marimgantl, Srinivasa ; Cheemala, Murthy N. ; Ahn, Jung Mo. / Novel amphiphilic α-helix mimetics based on a bis-benzamide scaffold. In: Organic Letters. 2009 ; Vol. 11, No. 19. pp. 4418-4421.
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