FR901483
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| Category | Antibiotics |
| Catalog number | BBF-03572 |
| CAS | |
| Molecular Weight | 426.44 |
| Molecular Formula | C20H31N2O6P |
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Description
FR901483 is originally isolated from Cladotryum sp. No. 11231. It has a strong immunosuppressive effect.
Specification
| IUPAC Name | [7-hydroxy-6-[(4-methoxyphenyl)methyl]-3-(methylamino)-5-azatricyclo[6.3.1.01,5]dodecan-9-yl] dihydrogen phosphate |
| Canonical SMILES | CNC1CC23CCC(C(C2)C(C(N3C1)CC4=CC=C(C=C4)OC)O)OP(=O)(O)O |
| InChI | InChI=1S/C20H31N2O6P/c1-21-14-10-20-8-7-18(28-29(24,25)26)16(11-20)19(23)17(22(20)12-14)9-13-3-5-15(27-2)6-4-13/h3-6,14,16-19,21,23H,7-12H2,1-2H3,(H2,24,25,26) |
| InChI Key | CIISYBZFZSWZLX-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Boiling Point | 627.0±65.0°C at 760 mmHg |
| Melting Point | 210-213°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Enantioselective total syntheses of (-)-FR901483 and (+)-8-epi-FR901483
Hao-Hua Huo, Xiao-Er Xia, Hong-Kui Zhang, Pei-Qiang Huang J Org Chem. 2013 Jan 18;78(2):455-65. doi: 10.1021/jo302362b. Epub 2012 Dec 18.
The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.
2. Biosynthesis of the Immunosuppressant (-)-FR901483
Zhuan Zhang, Yui Tamura, Mancheng Tang, Tianzhang Qiao, Michio Sato, Yoshihiro Otsu, Satoshi Sasamura, Masatoshi Taniguchi, Kenji Watanabe, Yi Tang J Am Chem Soc. 2021 Jan 13;143(1):132-136. doi: 10.1021/jacs.0c12352. Epub 2020 Dec 29.
We report characterization of the biosynthetic pathway of the potent immunosuppressant (-)-FR901483 (1) through heterologous expression and enzymatic assays. The biosynthetic logic to form the azatricyclic alkaloid is consistent with those proposed in biomimetic syntheses and involves aza-spiro annulation of dityrosyl-piperazine to form a ketoaldehyde intermediate, followed by regioselective aldol condensation, stereoselective ketoreduction, and phosphorylation. A possible target of 1 is proposed based on the biosynthetic studies.
3. Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation
Dominik Reich, Aaron Trowbridge, Matthew J Gaunt Angew Chem Int Ed Engl. 2020 Feb 3;59(6):2256-2261. doi: 10.1002/anie.201912010. Epub 2019 Dec 30.
We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (-)-FR901483 (1) and (+)-TAN1251C (2). A divergent synthetic strategy provides access to both natural products through a pivotal spirolactam intermediate (3), which can be accessed on a gram-scale. A photocatalytic olefin hydroaminoalkylation brings together three readily available building blocks and forges the majority of the carbon framework present in 1 and 2 in a single operation, leading to concise total syntheses. The complexity-generating photocatalytic process also provides direct access to novel non-racemic spirolactam scaffolds that are likely to be of interest to early-stage drug discovery programs.
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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 ╳
