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Conformational Analysis of β‐Lactam‐Containing Ferrocene Peptides
European Journal of Inorganic Chemistry, 2009-01, Vol.2009 (3), p.389-399
Kovač, Veronika
Radolović, Katarina
Habuš, Ivan
Siebler, Daniel
Heinze, Katja
Rapić, Vladimir
2009
Details
Autor(en) / Beteiligte
Kovač, Veronika
Radolović, Katarina
Habuš, Ivan
Siebler, Daniel
Heinze, Katja
Rapić, Vladimir
Titel
Conformational Analysis of β‐Lactam‐Containing Ferrocene Peptides
Ist Teil von
European Journal of Inorganic Chemistry, 2009-01, Vol.2009 (3), p.389-399
Ort / Verlag
Weinheim: WILEY‐VCH Verlag
Erscheinungsjahr
2009
Link zum Volltext
Quelle
Wiley Online Library Journals Frontfile Complete
Beschreibungen/Notizen
The homochiral 3‐amino‐1‐(4‐methoxyphenyl)‐4‐phenyl‐β‐lactam (≡ Alm) was conjugated with Boc‐Ala to give Ala‐Alm (9) after Boc deprotection (Boc = tert‐butoxycarbonyl, Ala = alanine). Coupling of Fc‐COOH (1) and Boc‐Fca (10) with “dipeptide” 9 resulted in the formation of Fc‐CO‐Ala‐Alm (12) and the trisamide Boc‐Fca‐Ala‐Alm (13), 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 = N‐(3‐dimethylaminopropyl)‐N′‐ethylcarbodiimide hydrochloride]. Symmetrically 1,1′‐disubstituted “tetrapeptide” Fn(CO‐Ala‐Alm)2 (14) was prepared by reaction of ferrocene chloride 11 with 9 (Fn = 1,1′‐ferrocenediyl). Spectroscopic and theoretical analyses revealed that compounds 12, 13, and 14 are stabilized in solution by medium‐strong intramolecular hydrogen bonds. In all dominant conformations (DFT calculations) intrachain bonds spanning COFc and NHAlm are present (γ‐turns). Additional interchain hydrogen bonds NHAla···COBoc (13) and NHAla···COAla/NHAla···COAlm (14) give rise to ordered helical conformations of the ferrocene moieties.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The synthesis and characterization of ferrocene bioconjugates with alanine and the β‐lactam [3‐amino‐1‐(4‐methoxyphenyl)‐4‐phenyl‐β‐lactam (≡ Alm)] Fc‐CO‐Ala‐Alm (12), Boc‐Fca‐Ala‐Alm (13), and Fn(CO‐Ala‐Alm)2 (14) is reported. The conformational preferences of these organometallic peptidomimetics in solution were determined experimentally and corroborated theoretically by DFT calculations.
Sprache
Englisch
Identifikatoren
ISSN: 1434-1948
eISSN: 1099-0682
DOI: 10.1002/ejic.200800913
Titel-ID: cdi_crossref_primary_10_1002_ejic_200800913
Format
–
Schlagworte
Conformation analysis
,
Density functional calculations
,
Hydrogen bonds
,
Metallocenes
,
Molecular modeling
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