A Lewis acid-mediated conformational switch

Peter C. Knipe, Hannah Lingard, Ian M. Jones, Sam Thompson, Andrew D. Hamilton

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site-the pyridyl nitrogen-increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained.

LanguageEnglish
Pages7937-7941
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number40
Early online date18 Aug 2014
DOIs
Publication statusPublished - 2014
Externally publishedYes

Fingerprint

Lewis Acids
Hydrogen
chemoreceptors
Hydrogen bonds
switches
Switches
Metalloporphyrins
hydrogen bonds
Liquid Crystals
acids
Alkynes
alkynes
Drug delivery
Amides
stimuli
amides
Conformations
delivery
drugs
Nitrogen

Cite this

Knipe, P. C., Lingard, H., Jones, I. M., Thompson, S., & Hamilton, A. D. (2014). A Lewis acid-mediated conformational switch. Organic and Biomolecular Chemistry, 12(40), 7937-7941. https://doi.org/10.1039/c4ob01556h
Knipe, Peter C. ; Lingard, Hannah ; Jones, Ian M. ; Thompson, Sam ; Hamilton, Andrew D. / A Lewis acid-mediated conformational switch. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 40. pp. 7937-7941.
@article{eb167030947f4fdc9e1513fbedfa4ad0,
title = "A Lewis acid-mediated conformational switch",
abstract = "Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site-the pyridyl nitrogen-increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained.",
author = "Knipe, {Peter C.} and Hannah Lingard and Jones, {Ian M.} and Sam Thompson and Hamilton, {Andrew D.}",
year = "2014",
doi = "10.1039/c4ob01556h",
language = "English",
volume = "12",
pages = "7937--7941",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "40",

}

Knipe, PC, Lingard, H, Jones, IM, Thompson, S & Hamilton, AD 2014, 'A Lewis acid-mediated conformational switch', Organic and Biomolecular Chemistry, vol. 12, no. 40, pp. 7937-7941. https://doi.org/10.1039/c4ob01556h

A Lewis acid-mediated conformational switch. / Knipe, Peter C.; Lingard, Hannah; Jones, Ian M.; Thompson, Sam; Hamilton, Andrew D.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 40, 2014, p. 7937-7941.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A Lewis acid-mediated conformational switch

AU - Knipe, Peter C.

AU - Lingard, Hannah

AU - Jones, Ian M.

AU - Thompson, Sam

AU - Hamilton, Andrew D.

PY - 2014

Y1 - 2014

N2 - Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site-the pyridyl nitrogen-increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained.

AB - Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site-the pyridyl nitrogen-increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained.

UR - http://www.scopus.com/inward/record.url?scp=84907484231&partnerID=8YFLogxK

U2 - 10.1039/c4ob01556h

DO - 10.1039/c4ob01556h

M3 - Article

VL - 12

SP - 7937

EP - 7941

JO - Organic and Biomolecular Chemistry

T2 - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 40

ER -