Biological activity of endomorphin and [Dmt1]endomorphin analogs with six-membered proline surrogates in position 2 was written by Perlikowska, Renata;Gach, Katarzyna;Fichna, Jakub;Toth, Geza;Walkowiak, Bogdan;do-Rego, Jean-Claude;Janecka, Anna. And the article was included in Bioorganic & Medicinal Chemistry in 2009.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:
Endogenous 渭-opioid receptor (MOR) selective peptides, endomorphin-1 (EM-1) and endomorphin-2 (EM-2), unlike so called typical opioids’, are characterized by the presence of Pro2 residue, which is a spacer connecting aromatic pharmacophoric residues. In order to investigate structural requirements for position 2, we synthesized endomorphin analogs incorporating, instead of Pro, unnatural amino acids with six-membered heterocyclic rings, such as piperidine 2-, 3- or 4-carboxylic acids (Pip, Nip and Inp, resp.). (R)-Nip residue turned out to be favorable for improving MOR affinity. Introduction of 2′,6′-dimethyltyrosine (Dmt) instead of Tyr1 led to obtaining [Dmt1, (R)-Nip2]EM-2 which showed exceptional MOR affinity and high stability against enzymic degradation in rat brain homogenate. In in vivo hot-plate test in mice, this analog given intracerebroventricularly (i.c.v.), produced profound supraspinal analgesia, being much more potent than EM-2. The antinociceptive effect of this analog lasted about 170 min and was almost completely reversed by 尾-funaltrexamine (尾-FNA), a selective MOR antagonist. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).
(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem