Chemoenzymatic Approach to Enantiopure Streptogramin B Variants: Characterization of Stereoselective Pristinamycin I Cyclase from Streptomyces pristinaespiralis was written by Mahlert, Christoph;Sieber, Stephan A.;Gruenewald, Jan;Marahiel, Mohamed A.. And the article was included in Journal of the American Chemical Society in 2005.Computed Properties of C21H21NO4 The following contents are mentioned in the article:
Streptogramin B antibiotics are cyclic peptide natural products produced by Streptomyces species. In combination with the synergistic group A component, they are last line of defense antimicrobial agents against multi-resistant cocci. The racemization sensitivity of the phenylglycine (Phg7) ester is a complex challenge in total chem. synthesis of streptogramin B mols. To provide fast and easy access to novel streptogramin antibiotics, we introduce a novel chemoenzymic strategy in which diversity is generated by standard solid phase protocols and stereoselectivity by subsequent enzymic cyclization. For this approach, we cloned, over-produced, and biochem. characterized the recombinant thioesterase domain SnbDE TE of the pristinamycin I nonribosomal peptide synthetase from Streptomyces pristinaespiralis. SnbDE TE catalyzes regioselective ring closure of linear peptide thioester analogs of pristinamycin I as well as stereoselective cyclization out of complex in situ racemizing substrate mixtures, enabling synthesis of Streptogramin B variants via a dynamic kinetic resolution assay. A remarkable substrate tolerance was detected for the enzymic cyclization including all the seven positions of the peptide backbone. Interestingly, SnbDE TE was observed to be the first cyclase from a macrolactone forming NRPS which is addnl. able to catalyze macrolactamization of peptide thioester substrates. An N-methylated peptide bond between positions 4 and 5 is mandatory for a high substrate turnover. The presented strategy is potent to screen for analogs with improved activity and guides our understanding of structure-activity relationships in the important class of streptogramin antibiotics. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Computed Properties of C21H21NO4).
(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. 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.Computed Properties of C21H21NO4
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem