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Issue 34, 2020
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Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction

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Abstract

Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using 1H NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbits via intramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.

Graphical abstract: Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction

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Supplementary files

Article information


Submitted
21 Jul 2020
Accepted
13 Aug 2020
First published
14 Aug 2020

Org. Biomol. Chem., 2020,18, 6643-6650
Article type
Paper

Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction

L. Yang, C. Ma, B. Kauffmann, D. Li and Q. Gan, Org. Biomol. Chem., 2020, 18, 6643
DOI: 10.1039/D0OB01503B

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