"Smart" rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes

W  Clegg; C  Gimenez-Saiz; D A  Leigh; A  Murphy; A M Z  Slawin; S J  Teat

"Smart" rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes

W Clegg, C Gimenez-Saiz, D A Leigh, A Murphy, A M Z Slawin, S J Teat

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

Abstract

The structures of the first tertiary amide peptide rotaxanes are established in solution by H-1 NMR spectroscopy and in the solid state by ii-ray crystallography. The hydrogen bonding networks which template the rotaxane formation "live on" in nonpolar solvents and strongly influence either the tertiary amide rotamer distribution or the rate of interconversion between the rotamers depending upon the peptide sequence. The intercomponent interactions-and their influences-can in appropriate cases be "switched off" by polar solvents leading to "smart" molecular systems which are flexible or adopt several shapes in one environment but transformed to rigid or single-shaped species in another.

Original language	English
Pages (from-to)	4124-4129
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	121
Issue number	17
Publication status	Published - 5 May 1999

Keywords

NUCLEAR MAGNETIC-RESONANCE
REDOX-ACTIVE <2>ROTAXANES
MOLECULAR SHUTTLES
<2>CATENANES
CATENANES
PEPTIDE
POLYROTAXANES
CONFORMATIONS
UMBRELLAS
MACHINES

Cite this

@article{c9f9cba255e84b1097ae89e3a648e3d4,

title = "{"}Smart{"} rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes",

abstract = "The structures of the first tertiary amide peptide rotaxanes are established in solution by H-1 NMR spectroscopy and in the solid state by ii-ray crystallography. The hydrogen bonding networks which template the rotaxane formation {"}live on{"} in nonpolar solvents and strongly influence either the tertiary amide rotamer distribution or the rate of interconversion between the rotamers depending upon the peptide sequence. The intercomponent interactions-and their influences-can in appropriate cases be {"}switched off{"} by polar solvents leading to {"}smart{"} molecular systems which are flexible or adopt several shapes in one environment but transformed to rigid or single-shaped species in another.",

keywords = "NUCLEAR MAGNETIC-RESONANCE, REDOX-ACTIVE <2>ROTAXANES, MOLECULAR SHUTTLES, <2>CATENANES, CATENANES, PEPTIDE, POLYROTAXANES, CONFORMATIONS, UMBRELLAS, MACHINES",

author = "W Clegg and C Gimenez-Saiz and Leigh, {D A} and A Murphy and Slawin, {A M Z} and Teat, {S J}",

year = "1999",

month = may,

day = "5",

language = "English",

volume = "121",

pages = "4124--4129",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society (ACS)",

number = "17",

}

TY - JOUR

T1 - "Smart" rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes

AU - Clegg, W

AU - Gimenez-Saiz, C

AU - Leigh, D A

AU - Murphy, A

AU - Slawin, A M Z

AU - Teat, S J

PY - 1999/5/5

Y1 - 1999/5/5

N2 - The structures of the first tertiary amide peptide rotaxanes are established in solution by H-1 NMR spectroscopy and in the solid state by ii-ray crystallography. The hydrogen bonding networks which template the rotaxane formation "live on" in nonpolar solvents and strongly influence either the tertiary amide rotamer distribution or the rate of interconversion between the rotamers depending upon the peptide sequence. The intercomponent interactions-and their influences-can in appropriate cases be "switched off" by polar solvents leading to "smart" molecular systems which are flexible or adopt several shapes in one environment but transformed to rigid or single-shaped species in another.

AB - The structures of the first tertiary amide peptide rotaxanes are established in solution by H-1 NMR spectroscopy and in the solid state by ii-ray crystallography. The hydrogen bonding networks which template the rotaxane formation "live on" in nonpolar solvents and strongly influence either the tertiary amide rotamer distribution or the rate of interconversion between the rotamers depending upon the peptide sequence. The intercomponent interactions-and their influences-can in appropriate cases be "switched off" by polar solvents leading to "smart" molecular systems which are flexible or adopt several shapes in one environment but transformed to rigid or single-shaped species in another.

KW - NUCLEAR MAGNETIC-RESONANCE

KW - REDOX-ACTIVE <2>ROTAXANES

KW - MOLECULAR SHUTTLES

KW - <2>CATENANES

KW - CATENANES

KW - PEPTIDE

KW - POLYROTAXANES

KW - CONFORMATIONS

KW - UMBRELLAS

KW - MACHINES

M3 - Article

SN - 0002-7863

VL - 121

SP - 4124

EP - 4129

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 17

ER -

"Smart" rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes

Abstract

Keywords

Fingerprint

Cite this