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Conformational Analysis of β-Lactam-Containing Ferrocene Peptides

✍ Scribed by Veronika Kovač; Katarina Radolović; Ivan Habuš; Daniel Siebler; Katja Heinze; Vladimir Rapić

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
942 KB
Volume
2009
Category
Article
ISSN
1434-1948

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✦ Synopsis

The homochiral 3-amino-1-(4-methoxyphenyl)-4-phenyl-βlactam (ϵ 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 ( ) and the trisamide Boc-Fca-Ala-Alm (13), respectively (Fc = ferrocenyl, Fca = 1Ј-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)-NЈ-ethylcarbodiimide hydrochloride]. Symmetrically 1,1Ј-disubstituted "tetrapeptide" Fn(CO-Ala-Alm) 2 (14)

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