(-)-Rasfonin
(Synonyms: 拉斯弗宁) 目录号 : GC45272
A fungal metabolite
Cas No.:303156-68-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(-)-Rasfonin is a fungal metabolite that has been found in T. terrophilus.1 It inhibits proliferation of mouse splenocytes induced by concanavalin A and LPS (IC50s = 0.7 and 0.5 μg/ml, respectively).
References
1. Fujimoto, H., Okamoto, Y., Sone, E., et al. Eleven new 2-pyrones from a fungi imperfecti, Trichurus terrophilus, found in a screening study guided by immunomodulatory activity. Chem. Pharm. Bull. (Tokyo) 53(8), 923-929 (2005).
| Cas No. | 303156-68-5 | SDF | |
| 别名 | 拉斯弗宁 | ||
| 化学名 | (2E,4E,6S)-8-hydroxy-6-(hydroxymethyl)-4-methyl-2,4-octadienoic acid, (2R,3R)-3,6-dihydro-6-oxo-2-[(1S,3R,5E)-1,3,5-trimethyl-5-hepten-1-yl]-2H-pyran-3-yl ester | ||
| Canonical SMILES | O=C1O[C@@]([C@@H](C)C[C@@H](C)C/C(C)=C/C)([H])[C@H](OC(/C=C/C(C)=C/[C@@H](CO)CCO)=O)C=C1 | ||
| 分子式 | C25H38O6 | 分子量 | 434.6 |
| 溶解度 | DMSO: 1 mg/ml,Ethanol: Soluble,Methanol: Soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.301 mL | 11.5048 mL | 23.0097 mL |
| 5 mM | 0.4602 mL | 2.301 mL | 4.6019 mL |
| 10 mM | 0.2301 mL | 1.1505 mL | 2.301 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective α-Hydroxymethylation Strategy
Org Lett 2018 Aug 17;20(16):5062-5065.PMID:30074398DOI:10.1021/acs.orglett.8b02222.
A scalable synthesis of the potent antitumor agent, (-)-Rasfonin, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both major fragments via catalytic enantioselective α-hydroxymethylation of simple aliphatic aldehydes. The route described has been successful in the generation of gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material to continue studies related to its mechanism of action and potential as a cancer therapeutic.
A concise asymmetric synthesis of (-)-Rasfonin
Org Biomol Chem 2012 Jan 7;10(1):29-31.PMID:22113704DOI:10.1039/c1ob06700a.
A very efficient total synthesis of the apoptosis inducer (-)-Rasfonin has been developed using CuBr/JosiPhos catalyzed iterative asymmetric conjugate addition of MeMgBr and Feringa's butenolide.
Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: application to a total synthesis of (-)-Rasfonin
J Am Chem Soc 2006 Aug 30;128(34):11032-3.PMID:16925414DOI:10.1021/ja063532+.
An enantioselective total synthesis of the apoptosis-inducing natural product, (-)-Rasfonin, is described. Camphor lactam-mediated asymmetric alkylation reactions enabled the installation of three stereogenic centers with >95:5 diastereoselectivity. A modified Corey-Peterson olefination was employed in the construction of the (E,E)-diene system. A highly diastereoselective, asymmetric vinylogous Mukaiyama aldol addition was conducted using a chiral cationic oxazaborolidine catalyst. The pyranone core of the natural product was prepared via a DBU-promoted rearrangement of a furanol to its corresponding pyranol with concomitant [1,4]-silyl transfer.
One-Step Homologation for the Catalytic Asymmetric Synthesis of Deoxypropionates
Chemistry 2017 Jan 1;23(1):149-156.PMID:27739117DOI:10.1002/chem.201604478.
A one-step homologation protocol for the synthesis of natural products containing deoxypropionate motif is described by the combination of Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-Pd-catalyzed vinylation and ZACA-oxidation reaction. In contrast to most other synthetic strategies used to date that typically require three steps per deoxypropionate unit due to the functional-group interconversions, our one-step homologation strategy promises to provide a general and more efficient synthetic route toward deoxypropionate natural products as exemplified by significant improvements in the syntheses of intermediates and/or final products of mycolipenic acid 1 and its analogue 2, (-)-Rasfonin, and syn- and anti-dicarboxylic acids 5 and 6.