The first ferrocene analogues of muramyldipeptide

Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate

“…[23] The most stable were reoptimized in chloroform (using IEF-PCM to describe implicit solvent effects) with the B3LYP method and 6-311+G(d,p) basis set. [29] Boc-AA-Fca-OMe (2a/2b): The syntheses of 2a and 2b were performed according to our recent paper: [9] the fully protected ferrocene amino acid Boc-Fca-OMe [5] (1) was N-deprotected by gaseous HCl in EtOAc to give the hydrochloride salt, which was treated with NEt 3 and coupled with Boc-AA-OH (AA = l-, d-Ala, previously activated by using EDC and HOBt). Quantum mechanical calculations were performed with Gaussian 09, v.A.02.…”

“…Thereby, we applied a strategy similar to that conducted previously, [6][7][8][9] based on a comparison of the spectroscopic data of a reference, a model, and the new compounds. Thereby, we applied a strategy similar to that conducted previously, [6][7][8][9] based on a comparison of the spectroscopic data of a reference, a model, and the new compounds.…”

“…In this connection, the IR data presented in Table 1 imply the nonhydrogen-bonded states of 4-6 and the hydrogen-bonded states of 7-9. [6][7][8][9] Taking their structures into account, intramolecular hydrogen bonding in monosubstituted ferrocene 7 might be achieved in an intrachain manner to lead to tentative conformations A and B, whereas disubstituted 8 and 9 could be stabilized through interchain IHBs ( Figure 4). IR spectroscopic data [a] (cm -1 ) and 1 H NMR chemical shifts [b] of the NH protons (ppm) of 4-9.…”

“…The ferrocene peptides VII were obtained by coupling C-protected Fca with Boc-L-Ala-OH and Boc-D-Ala-OH, respectively. [29] Boc-AA-Fca-OMe (2a/2b): The syntheses of 2a and 2b were performed according to our recent paper: [9] the fully protected ferrocene amino acid Boc-Fca-OMe [5] (1) was N-deprotected by gaseous HCl in EtOAc to give the hydrochloride salt, which was treated with NEt 3 and coupled with Boc-AA-OH (AA = l-, d-Ala, previously activated by using EDC and HOBt). Double resonance experiments (COSY, NOESY, and HMBC) were performed in order to assist in signal assignment.…”

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

“…Ferrocene-based redox active species have already garnered considerable attention due to their small size, good stability, convenient synthetic access, easy chemical modification, relative lipophilicity, and ease of redox tuning. 3,[30][31][32][33][34][35][36][37][38][39][40][41][42] Small molecules based on the ferrocene core have been used extensively as detectors of metal ions and small molecules. [32][33][34][35][36][37][38]43 Systems targeting larger species such as biomolecules have utilized the attachment of large antibodies or immunoglobulins to ferrocene derivatives that have been embedded onto an electrochemical surface.…”