FR 252921
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03557 |
| CAS | |
| Molecular Weight | 500.67 |
| Molecular Formula | C29H44N2O5 |
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Description
FR 252921 is produced by the strain of Pseudomonas fluorenscens No. 408813. It shows immunosuppressive effect in mice in vivo and in vitro, and has synergistic effect with FK-506.
Specification
| IUPAC Name | (13E,15E,17E)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-7-hydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-13,15,17-triene-4,9,19-trione |
| Canonical SMILES | CCCCCCCC=CC=C(C)C1CC(=O)NCC(C(C(=O)NCCC=CC=CC=CC(=O)O1)C)O |
| InChI | InChI=1S/C29H44N2O5/c1-4-5-6-7-8-9-12-15-18-23(2)26-21-27(33)31-22-25(32)24(3)29(35)30-20-17-14-11-10-13-16-19-28(34)36-26/h10-16,18-19,24-26,32H,4-9,17,20-22H2,1-3H3,(H,30,35)(H,31,33)/b13-10-,14-11-,15-12+,19-16-,23-18- |
| InChI Key | BMWFPIGVZGRBAD-JYDGBYIJSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 140-144°C |
Reference Reading
1. A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants
Yong Chen, Guilhem Coussanes, Caroline Souris, Paul Aillard, Dainis Kaldre, Kathrin Runggatscher, Stefan Kubicek, Giovanni Di Mauro, Boris Maryasin, Nuno Maulide J Am Chem Soc. 2019 Sep 4;141(35):13772-13777. doi: 10.1021/jacs.9b07185. Epub 2019 Aug 22.
FR252921, FR252922, and FR256523 are a family of potent macrocyclic polyene immunosuppressive agents with a novel mode of action. However, the lack of an efficient and flexible synthesis has hindered further biological studies, mostly due to the fact that the natural products appear to be kinetic isomers regarding the triene moiety. Herein, we report the development and application of an unprecedented, unique domino Suzuki-Miyaura/4π-electrocyclic ring-opening macrocyclization, resulting in a concise, unified, and stereoselective synthetic route to these complex targets in only 10 steps. This in turn enables ready access to a range of unnatural analogues, among which several compounds showed inhibition of T-lymphocyte proliferation at levels equal or superior to those of the natural products themselves.
2. Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B
Dominique Amans, Véronique Bellosta, Janine Cossy Chemistry. 2009;15(14):3457-73. doi: 10.1002/chem.200802649.
Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from a common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the triene moieties, and a Stille cross-coupling to install the dienic units.
3. Synthesis of Polyene Bioactive Natural Products: FR252921 and Vitamin A
Dattatraya H Dethe, Vimlesh Kumar, Nagabhushana C Beeralingappa, Kunj B Mishra, Appasaheb K Nirpal Org Lett. 2022 Mar 25;24(11):2203-2207. doi: 10.1021/acs.orglett.2c00546. Epub 2022 Mar 11.
A formal synthesis of FR252921, a potent macrocyclic immunosuppressive agent, and a six-step synthesis of vitamin A have been demonstrated. The application of a ruthenium-catalyzed step-economic and environmentally benign strategy for the highly stereo- and chemoselective construction of valuable polyene motifs of FR252921 and vitamin A highlights the syntheses. The key features for the synthesis FR252921 include preparation of the triene moiety followed by two consecutive peptide couplings of the three fragments.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
