Conformational analysis of β-lactam-containing ferrocene peptides

Publication type:
Journal article
Metadata:
Autoren
  • Veronika Kovač
  • Katarina Radolović
  • Ivan Habuš
  • Daniel Siebler
  • Katja Heinze
  • Vladimir Rapić
Sammlungen
  • metadata
ISSN
1434-1948
Ausgabe der Veröffentlichung
3
Zeitschrift
European journal of inorganic chemistry
Schlüsselwörter
  • 540 Chemie
  • 540 Chemistry and allied sciences
Sprache
eng
Paginierung
Seiten: 389 - 399
Datum der Veröffentlichung
2009
Herausgeber
Wiley-VCH Verl.
Herausgeber URL
http://dx.doi.org/10.1002/ejic.200800913
Datum der Datenerfassung
2020
Datum, an dem der Datensatz öffentlich gemacht wurde
2020
Zugang
Public
Titel
Conformational analysis of β-lactam-containing ferrocene peptides
Ausgabe der Zeitschrift
2009

Data source: METADATA.UB

Other metadata sources:
Autoren
  • Veronika Kovac
  • Katarina Radolovic
  • Ivan Habus
  • Daniel Siebler
  • Katja Heinze
  • Vladimir Rapic
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000263086900006&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/ejic.200800913
eISSN
1099-0682
Externe Identifier
  • Clarivate Analytics Document Solution ID: 403MO
ISSN
1434-1948
Ausgabe der Veröffentlichung
3
Zeitschrift
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Schlüsselwörter
  • Conformation analysis
  • Density functional calculations
  • Hydrogen bonds
  • Metallocenes
  • Molecular modeling
Paginierung
389 - 399
Datum der Veröffentlichung
2009
Status
Published
Titel
Conformational Analysis of β-Lactam-Containing Ferrocene Peptides
Sub types
  • Article

Data source: Web of Science (Lite)

Abstract
<jats:title>Abstract</jats:title><jats:p>The homochiral 3‐amino‐1‐(4‐methoxyphenyl)‐4‐phenyl‐β‐lactam (≡ Alm) was conjugated with Boc‐Ala to give Ala‐Alm (<jats:bold>9</jats:bold>) after Boc deprotection (Boc = <jats:italic>tert</jats:italic>‐butoxycarbonyl, Ala = alanine). Coupling of Fc‐COOH (<jats:bold>1</jats:bold>) and Boc‐Fca (<jats:bold>10</jats:bold>) with “dipeptide” <jats:bold>9</jats:bold> resulted in the formation of Fc‐CO‐Ala‐Alm (<jats:bold>12</jats:bold>) and the trisamide Boc‐Fca‐Ala‐Alm (<jats:bold>13</jats:bold>), respectively (Fc = ferrocenyl, Fca = 1′‐aminoferrocene‐1‐carboxylic acid). The reactions were accomplished by the HOBt/EDC procedure, and the products were obtained in good yields [HOBt = 1‐hydroxybenzotriazole, EDC = <jats:italic>N</jats:italic>‐(3‐dimethylaminopropyl)‐<jats:italic>N</jats:italic>′‐ethylcarbodiimide hydrochloride]. Symmetrically 1,1′‐disubstituted “tetrapeptide” Fn(CO‐Ala‐Alm)<jats:sub>2</jats:sub> (<jats:bold>14</jats:bold>) was prepared by reaction of ferrocene chloride <jats:bold>11</jats:bold> with <jats:bold>9</jats:bold> (Fn = 1,1′‐ferrocenediyl). Spectroscopic and theoretical analyses revealed that compounds <jats:bold>12</jats:bold>, <jats:bold>13</jats:bold>, and <jats:bold>14</jats:bold> are stabilized in solution by medium‐strong intramolecular hydrogen bonds. In all dominant conformations (DFT calculations) intrachain bonds spanning CO<jats:sub>Fc</jats:sub> and NH<jats:sub>Alm</jats:sub> are present (γ‐turns). Additional interchain hydrogen bonds NH<jats:sub>Ala</jats:sub><jats:bold>···</jats:bold>CO<jats:sub>Boc</jats:sub> (<jats:bold>13</jats:bold>) and NH<jats:sub>Ala</jats:sub><jats:bold>···</jats:bold>CO<jats:sub>Ala</jats:sub>/NH<jats:sub>Ala</jats:sub><jats:bold>···</jats:bold>CO<jats:sub>Alm</jats:sub> (<jats:bold>14</jats:bold>) give rise to ordered helical conformations of the ferrocene moieties.(© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>
Autoren
  • Veronika Kovač
  • Katarina Radolović
  • Ivan Habuš
  • Daniel Siebler
  • Katja Heinze
  • Vladimir Rapić
DOI
10.1002/ejic.200800913
eISSN
1099-0682
ISSN
1434-1948
Ausgabe der Veröffentlichung
3
Zeitschrift
European Journal of Inorganic Chemistry
Sprache
en
Online publication date
2009
Paginierung
389 - 399
Datum der Veröffentlichung
2009
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/ejic.200800913
Datum der Datenerfassung
2023
Titel
Conformational Analysis of β‐Lactam‐Containing Ferrocene Peptides
Ausgabe der Zeitschrift
2009

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