Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayersCitation formats

  • External authors:
  • Francis Lister
  • Natasha Eccles
  • Sarah J. Pike
  • Robert A. Brown
  • George Whitehead
  • James Raftery
  • Jonathan Clayden

Standard

Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers. / Lister, Francis; Eccles, Natasha; Pike, Sarah J.; Brown, Robert A.; Whitehead, George; Raftery, James; Webb, Simon; Clayden, Jonathan.

In: Chemical Science, 2018.

Research output: Contribution to journalArticle

Harvard

Lister, F, Eccles, N, Pike, SJ, Brown, RA, Whitehead, G, Raftery, J, Webb, S & Clayden, J 2018, 'Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers', Chemical Science. https://doi.org/10.1039/C8SC02532K

APA

Lister, F., Eccles, N., Pike, S. J., Brown, R. A., Whitehead, G., Raftery, J., ... Clayden, J. (2018). Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers. Chemical Science. https://doi.org/10.1039/C8SC02532K

Vancouver

Lister F, Eccles N, Pike SJ, Brown RA, Whitehead G, Raftery J et al. Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers. Chemical Science. 2018. https://doi.org/10.1039/C8SC02532K

Author

Lister, Francis ; Eccles, Natasha ; Pike, Sarah J. ; Brown, Robert A. ; Whitehead, George ; Raftery, James ; Webb, Simon ; Clayden, Jonathan. / Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers. In: Chemical Science. 2018.

Bibtex

@article{93a7b459d29b4d499342b452792f3b30,
title = "Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers",
abstract = "Exploring the detailed structural features of synthetic molecules in the membrane phase requires sensitive probes of conformation. Here we describe the design, synthesis and characterization of bis(pyrene) probes that report conformational changes in membrane-active dynamic foldamers. The probes were designed to distinguish between left-handed (M) and right-handed (P) screw-sense conformers of 310-helical α-aminoisobutyric acid (Aib) peptide foldamers, both in solution and in bilayer membranes. Several different bis(pyrene) probes were synthesized and ligated to the C-terminus of Aib tetramers that had different chiral residues at the N-terminus, residues that favored either an M or a P screw-sense in the 310-helix. The readily synthesized and conveniently incorporated N-acetyl-1,2-bis(pyren-1’-yl)ethylenediamine probe proved to have the best properties. In solution, changes in foldamer screw-sense induced substantial changes in the ratio of excimer/monomer fluorescence emission (E/M) for this reporter of conformation, with X-ray crystallography revealing that opposite screw-senses produce very different interpyrene distances in the reporter. In bilayers, this convenient and sensitive fluorescent reporter allowed, for the first time, an investigation of how the chirality of natural phospholipids affects foldamer conformation.",
author = "Francis Lister and Natasha Eccles and Pike, {Sarah J.} and Brown, {Robert A.} and George Whitehead and James Raftery and Simon Webb and Jonathan Clayden",
year = "2018",
doi = "10.1039/C8SC02532K",
language = "English",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",

}

RIS

TY - JOUR

T1 - Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers

AU - Lister, Francis

AU - Eccles, Natasha

AU - Pike, Sarah J.

AU - Brown, Robert A.

AU - Whitehead, George

AU - Raftery, James

AU - Webb, Simon

AU - Clayden, Jonathan

PY - 2018

Y1 - 2018

N2 - Exploring the detailed structural features of synthetic molecules in the membrane phase requires sensitive probes of conformation. Here we describe the design, synthesis and characterization of bis(pyrene) probes that report conformational changes in membrane-active dynamic foldamers. The probes were designed to distinguish between left-handed (M) and right-handed (P) screw-sense conformers of 310-helical α-aminoisobutyric acid (Aib) peptide foldamers, both in solution and in bilayer membranes. Several different bis(pyrene) probes were synthesized and ligated to the C-terminus of Aib tetramers that had different chiral residues at the N-terminus, residues that favored either an M or a P screw-sense in the 310-helix. The readily synthesized and conveniently incorporated N-acetyl-1,2-bis(pyren-1’-yl)ethylenediamine probe proved to have the best properties. In solution, changes in foldamer screw-sense induced substantial changes in the ratio of excimer/monomer fluorescence emission (E/M) for this reporter of conformation, with X-ray crystallography revealing that opposite screw-senses produce very different interpyrene distances in the reporter. In bilayers, this convenient and sensitive fluorescent reporter allowed, for the first time, an investigation of how the chirality of natural phospholipids affects foldamer conformation.

AB - Exploring the detailed structural features of synthetic molecules in the membrane phase requires sensitive probes of conformation. Here we describe the design, synthesis and characterization of bis(pyrene) probes that report conformational changes in membrane-active dynamic foldamers. The probes were designed to distinguish between left-handed (M) and right-handed (P) screw-sense conformers of 310-helical α-aminoisobutyric acid (Aib) peptide foldamers, both in solution and in bilayer membranes. Several different bis(pyrene) probes were synthesized and ligated to the C-terminus of Aib tetramers that had different chiral residues at the N-terminus, residues that favored either an M or a P screw-sense in the 310-helix. The readily synthesized and conveniently incorporated N-acetyl-1,2-bis(pyren-1’-yl)ethylenediamine probe proved to have the best properties. In solution, changes in foldamer screw-sense induced substantial changes in the ratio of excimer/monomer fluorescence emission (E/M) for this reporter of conformation, with X-ray crystallography revealing that opposite screw-senses produce very different interpyrene distances in the reporter. In bilayers, this convenient and sensitive fluorescent reporter allowed, for the first time, an investigation of how the chirality of natural phospholipids affects foldamer conformation.

U2 - 10.1039/C8SC02532K

DO - 10.1039/C8SC02532K

M3 - Article

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

ER -