The effect of chemical modification on the solution structure of derivatives of substance P: Nuclear magnetic resonance study of substituted and retroinverso analogues

Gennaro Esposito, Luigi Settembri, Giuseppe C. Viscomi, Neri Niccolai

Research output: Contribution to journalArticle

Abstract

Four derivatives of the bioactive fragment 6-11 of Substance P were characterized by means of one- and two-dimensional 1H n.m.r. spectroscopy. Indirect evidence of backbone folding for these hexapeptides was given by temperature coefficients and paramagnetic relaxation rate enhancements of the amide protons. Chemical modifications were found to modulate the solution structure. Retro-inversion caused some conformational changes and a correlation between these structural variations and the relative biological activities was attempted.

Original languageEnglish (US)
Pages (from-to)1313-1318
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number7
DOIs
StatePublished - Jan 1 1988

Fingerprint

Chemical modification
Substance P
Bioactivity
Amides
Protons
Nuclear magnetic resonance
Spectroscopy
Derivatives
Temperature
substance P (6-11)

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{610a932d812e4e1fb6a84707e8300feb,
title = "The effect of chemical modification on the solution structure of derivatives of substance P: Nuclear magnetic resonance study of substituted and retroinverso analogues",
abstract = "Four derivatives of the bioactive fragment 6-11 of Substance P were characterized by means of one- and two-dimensional 1H n.m.r. spectroscopy. Indirect evidence of backbone folding for these hexapeptides was given by temperature coefficients and paramagnetic relaxation rate enhancements of the amide protons. Chemical modifications were found to modulate the solution structure. Retro-inversion caused some conformational changes and a correlation between these structural variations and the relative biological activities was attempted.",
author = "Gennaro Esposito and Luigi Settembri and Viscomi, {Giuseppe C.} and Neri Niccolai",
year = "1988",
month = "1",
day = "1",
doi = "10.1039/P29880001313",
language = "English (US)",
pages = "1313--1318",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Chemical Society",
number = "7",

}

TY - JOUR

T1 - The effect of chemical modification on the solution structure of derivatives of substance P

T2 - Nuclear magnetic resonance study of substituted and retroinverso analogues

AU - Esposito, Gennaro

AU - Settembri, Luigi

AU - Viscomi, Giuseppe C.

AU - Niccolai, Neri

PY - 1988/1/1

Y1 - 1988/1/1

N2 - Four derivatives of the bioactive fragment 6-11 of Substance P were characterized by means of one- and two-dimensional 1H n.m.r. spectroscopy. Indirect evidence of backbone folding for these hexapeptides was given by temperature coefficients and paramagnetic relaxation rate enhancements of the amide protons. Chemical modifications were found to modulate the solution structure. Retro-inversion caused some conformational changes and a correlation between these structural variations and the relative biological activities was attempted.

AB - Four derivatives of the bioactive fragment 6-11 of Substance P were characterized by means of one- and two-dimensional 1H n.m.r. spectroscopy. Indirect evidence of backbone folding for these hexapeptides was given by temperature coefficients and paramagnetic relaxation rate enhancements of the amide protons. Chemical modifications were found to modulate the solution structure. Retro-inversion caused some conformational changes and a correlation between these structural variations and the relative biological activities was attempted.

UR - http://www.scopus.com/inward/record.url?scp=1842317251&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1842317251&partnerID=8YFLogxK

U2 - 10.1039/P29880001313

DO - 10.1039/P29880001313

M3 - Article

AN - SCOPUS:1842317251

SP - 1313

EP - 1318

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1470-1820

IS - 7

ER -