Approaching an experimental electron density model of the biologically active trans-epoxysuccinyl amide group—Substituent effects vs. crystal packing

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Ming W Shi
  • Scott G Stewart
  • Alexandre N Sobolev
  • Birger Dittrich
  • Tanja Schirmeister
  • Peter Luger
  • Malte Hesse
  • Yu-Sheng Chen
  • Peter R Spackman
  • Mark A Spackman
  • Simon Grabowsky
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000412844400003&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/poc.3683
eISSN
1099-1395
Externe Identifier
  • Clarivate Analytics Document Solution ID: FJ6DN
ISSN
0894-3230
Ausgabe der Veröffentlichung
11
Zeitschrift
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Schlüsselwörter
  • electron density
  • epoxysuccinyl peptides
  • invarioms
  • model energies
  • protease inhibitors
Artikelnummer
ARTN e3683
Datum der Veröffentlichung
2017
Status
Published
Titel
Approaching an experimental electron density model of the biologically active <i>trans</i>-epoxysuccinyl amide group-Substituent effects vs. crystal packing
Sub types
  • Article
Ausgabe der Zeitschrift
30

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title><jats:p>The <jats:italic>trans</jats:italic>‐epoxysuccinyl amide group as a biologically active moiety in cysteine protease inhibitors such as loxistatin acid E64c has been used as a benchmark system for theoretical studies of environmental effects on the electron density of small active ingredients in relation to their biological activity. Here, the synthesis and the electronic properties of the smallest possible active site model compound are reported to close the gap between the unknown experimental electron density of <jats:italic>trans</jats:italic>‐epoxysuccinyl amides and the well‐known function of related drugs. Intramolecular substituent effects are separated from intermolecular crystal packing effects on the electron density, which allows us to predict the conditions under which an experimental electron density investigation on <jats:italic>trans</jats:italic>‐epoxysuccinyl amides will be possible. In this context, the special importance of the carboxylic acid function in the model compound for both crystal packing and biological activity is revealed through the novel tool of model energy analysis.</jats:p>
Autoren
  • Ming W Shi
  • Scott G Stewart
  • Alexandre N Sobolev
  • Birger Dittrich
  • Tanja Schirmeister
  • Peter Luger
  • Malte Hesse
  • Yu‐Sheng Chen
  • Peter R Spackman
  • Mark A Spackman
  • Simon Grabowsky
DOI
10.1002/poc.3683
eISSN
1099-1395
ISSN
0894-3230
Ausgabe der Veröffentlichung
11
Zeitschrift
Journal of Physical Organic Chemistry
Sprache
en
Online publication date
2017
Datum der Veröffentlichung
2017
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/poc.3683
Datum der Datenerfassung
2023
Titel
Approaching an experimental electron density model of the biologically active <i>trans</i>‐epoxysuccinyl amide group—Substituent effects vs. crystal packing
Ausgabe der Zeitschrift
30

Datenquelle: Crossref

Autoren
  • Ming W Shi
  • Scott G Stewart
  • Alexandre N Sobolev
  • Birger Dittrich
  • Tanja Schirmeister
  • Peter Luger
  • Malte Hesse
  • Yu-Sheng Chen
  • Peter R Spackman
  • Mark A Spackman
  • others
Zeitschrift
Journal of Physical Organic Chemistry
Artikelnummer
11
Paginierung
e3683 - e3683
Datum der Veröffentlichung
2017
Datum der Datenerfassung
2021
Titel
Approaching an experimental electron density model of the biologically active trans-epoxysuccinyl amide group—Substituent effects vs. crystal packing
Sub types
  • article
Ausgabe der Zeitschrift
30

Datenquelle: Manual

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