Synthese von ruthenocenoyl ‐ 1‐1, 1′‐diglycin ‐ ethylester durch Austausch von Ferrocenoyl‐glycinester mit ¹⁰³RuCl₃

Abstract

Exchange yielding R u t h e n o c e n o y l -g l y c i n e -D e r i v a t i v e s react i o n of Ferrocen oy 1 -9 1 y c i net hy 1 ester w i t h 03RuC 1 Summary: Ruthenocenoyl-glycine derivatives labelled with radioactive ruthenium (g7Ru, lo3Ru). showing a clearance similar t o Hippuran, are potential r a d i o p h a r m a c e u t i c a l s . S y n t h e s i s , reaction mechanism and identification o f r u t h e n o c e n o y l -1 . 1 ' -d i g l y c i n e derivatives are described. Einleitung: Ruthenocenoy mi t radioakt -glycin (Ruppuran) und -diglycin kann man leicht vem Ruthenium als Zentralatom markieren. Beide Ruthenocen-Derivate haben interessante biochemische Eigenschaften: Sie werden ahnlich w i e das Radiopharmakon o-clod-Hippursaure (Hippuran) primar von der Niere akkumuliert und eden (1,2). D a diese werden u n d im Urin sie z u r Bestimmung anschliei3end extrem schnell renal ausgesch Ruthenocen-Verbindungen nicht metabolisier nur die Ausgangs-Produkte erscheinen, sind der Nieren-Funktion gut geeignet.

Changes in the hydrogen bonding pattern in ferrocene peptides

“…The Fc substitution pattern shows the two podand glycineethylesters in a 1,3 0 -conformation. The absence of the 1,2 0 -conformation with its crossstrand H-bonding motif in this system is surprising and was not be predicted based on the available literature [6,7,[9][10][11][12][13]. Other features displayed by compound 1, such as the co-planarity of the Cp rings (1.8°) and the small Cp-amide twist angle (Cp1-amide: 14.1°and Cp2-amide 15.2°) are common to many ferrocene amides [8,9c,23,24].…”

“…We chose to focus on 1,1 0 -bis(glycine)ferrocenes having two podand glycine substitutents. This system was used before in transmetallations reactions but was never structurally characterized [13]. Although disubstituted ferrocenes in general are conformationally highly adaptable, 1,2 0 -and 1,3 0 -conformers are sterically preferred, whereas in the presence of strong intermolecular interactions the eclipsed 1,1 0 -conformer can be favored [14].…”

Ferrocenoyl-amino acids: redox response towards di- and trivalent metal ions

“…Fc-CO-Gly-OH (2a) [28,29], Fc-CO-Asp(OMe) 2 (3a-OMe), Fc-CO-Asp-OH (3a) [31], Fc-COGlu(OEt) 2 (4a-OEt) [32] were all prepared according to the literature procedures, 1,1 0 -Fc(CO-Gly-OEt) 2 (2b-OEt) and 1,1 0 -Fc(CO-Gly-OH) 2 (2b) were synthesized as reported before [33,34]. Full details of their characterization are given in supplemental material.…”

Synthesis and characterisation of a ruthenocenoyl bioconjugate with the cyclic octapeptide octreotate

“…A few cobaltocenium conjugates with peptide nucleic acid oligomers (PNA) [10,11] and peptides [12][13][14][15] have been published by our group. Ruthenocene has been mentioned in a few early papers exclusively in the context of radiolabelling with 103 Ru [16][17][18][19], and more recently labelling of estradiol by ruthenocene was proposed by Jaouen and coworkers [20]. Gmeiner et al have recently reported ruthenocene derivatives of dopamine receptor ligands which show an increased affinity and specificity for the D4 dopamine receptor subtypes compared to their metal-free congeners [21].…”