Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

Sarah J. Pike; Matteo De Poli; Wojciech Zawodny; James Raftery; Simon J. Webb; Jonathan Clayden

doi:10.1039/c3ob40463c

Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

Sarah J. Pike, Matteo De Poli, Wojciech Zawodny, James Raftery, Simon J. Webb, Jonathan Clayden

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

Abstract

Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference. © The Royal Society of Chemistry 2013.

Original language	English
Pages (from-to)	3168-3176
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	19
DOIs	https://doi.org/10.1039/c3ob40463c
Publication status	Published - 2013

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10.1039/c3ob40463c

CCDC 913267: Experimental Crystal Structure Determination
Pike, S. J. (Contributor), De Poli, M. (Contributor), Zawodny, W. (Contributor), Raftery, J. (Contributor), Webb, S. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 29 Nov 2012
DOI: 10.5517/ccznb75, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccznb75&sid=DataCite
Dataset
CCDC 913266: Experimental Crystal Structure Determination
Pike, S. J. (Contributor), De Poli, M. (Contributor), Zawodny, W. (Contributor), Raftery, J. (Contributor), Webb, S. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2012
DOI: 10.5517/ccznb64, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccznb64&sid=DataCite
Dataset
CCDC 927332: Experimental Crystal Structure Determination
Pike, S. J. (Contributor), De Poli, M. (Contributor), Zawodny, W. (Contributor), Raftery, J. (Contributor), Webb, S. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/cc103yy0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc103yy0&sid=DataCite
Dataset

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@article{70227bc15c7944c78fca5aaaa59cf5ab,

title = "Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers",

abstract = "Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference. {\textcopyright} The Royal Society of Chemistry 2013.",

author = "Pike, {Sarah J.} and {De Poli}, Matteo and Wojciech Zawodny and James Raftery and Webb, {Simon J.} and Jonathan Clayden",

note = "I007962, Biotechnology and Biological Sciences Research Council, United Kingdom",

year = "2013",

doi = "10.1039/c3ob40463c",

language = "English",

volume = "11",

pages = "3168--3176",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

AU - Pike, Sarah J.

AU - De Poli, Matteo

AU - Zawodny, Wojciech

AU - Raftery, James

AU - Webb, Simon J.

AU - Clayden, Jonathan

N1 - I007962, Biotechnology and Biological Sciences Research Council, United Kingdom

PY - 2013

Y1 - 2013

N2 - Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference. © The Royal Society of Chemistry 2013.

AB - Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference. © The Royal Society of Chemistry 2013.

U2 - 10.1039/c3ob40463c

DO - 10.1039/c3ob40463c

M3 - Article

C2 - 23558640

SN - 1477-0520

VL - 11

SP - 3168

EP - 3176

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 19

ER -

Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

Abstract

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Datasets

CCDC 913267: Experimental Crystal Structure Determination

CCDC 913266: Experimental Crystal Structure Determination

CCDC 927332: Experimental Crystal Structure Determination

Cite this