Synthesis and Conformational Analysis of Efrapeptins was written by Weigelt, Sven;Huber, Thomas;Hofmann, Frank;Jost, Micha;Ritzefeld, Markus;Luy, Burkhard;Freudenberger, Christoph;Majer, Zsuzsanna;Vass, Elemer;Greie, Joerg-Christian;Panella, Lavinia;Kaptein, Bernard;Broxterman, Quirinus B.;Kessler, Horst;Altendorf, Karlheinz;Hollosi, Miklos;Sewald, Norbert. And the article was included in Chemistry – A European Journal in 2012.Synthetic Route of C21H21NO4 The following contents are mentioned in the article:
The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidum are inhibitors of F1-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in C伪-dialkyl amino acids (Aib, Iva, Acc) and contain one 尾-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogs of efrapeptin C were synthesized using 伪-azido carboxylic acids as masked amino acid derivatives All compounds display inhibitory activity toward F1-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogs were shown to adopt helical conformations in solution In the case of efrapeptin C, VCD spectra proved that a 310-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and mol. modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational anal. and confirmed the 310-helical conformation. Safety: caution is advised with low-mol.-weight azido compounds This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Synthetic Route of C21H21NO4).
(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Synthetic Route of C21H21NO4
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem