Reveromycin B
(Synonyms: 雷弗霉素B) 目录号 : GC40070
A bacterial metabolite
Cas No.:144860-68-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Reveromycin B is a spiroketal bacterial metabolite originally isolated from Streptomyces. It inhibits EGF-induced mitogenic activity in Balb/MK cells (IC50 = 6 μg/ml) and exhibits pH-dependent antifungal activity against C. albicans (MICs = 15.6 and >500 μg/ml at pH 3.0 and 7.4, respectively). Unlike reveromycin A and reveromycin C , reveromycin B does not inhibit proliferation of KB and K562 cells.
| Cas No. | 144860-68-4 | SDF | |
| 别名 | 雷弗霉素B | ||
| Canonical SMILES | CC(/C=C/[C@@H]([C@H](/C=C/C(O)=O)C)O)=C\C[C@H]1O[C@@]2(CC[C@@]([C@H](/C=C/C(C)=C/C(O)=O)OC(CCC(O)=O)=O)(CCCC)O2)CC[C@@H]1C | ||
| 分子式 | C36H52O11 | 分子量 | 660.8 |
| 溶解度 | Soluble in DMSO | 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 | 1.5133 mL | 7.5666 mL | 15.1332 mL |
| 5 mM | 0.3027 mL | 1.5133 mL | 3.0266 mL |
| 10 mM | 0.1513 mL | 0.7567 mL | 1.5133 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。
Stereoselective total synthesis of Reveromycin B and C19-epi-reveromycin B
Chemistry 2000 Jun 2;6(11):1987-2001.PMID:10894398DOI:10.1002/1521-3765(20000602)6:11<1987::aid-chem1987>3.0.co;2-u.
Our studies toward the total synthesis of the reveromycin family of natural products are described herein. Our synthetic approach is efficient, stereocontrolled, and convergent and has resulted in the first synthesis of Reveromycin B (4) and C19-epi-reveromycin B (55). Key steps of this successful strategy include: a modified Negishi coupling (construction of C7-C8 bond) and a Kishi-Nozaki reaction (construction of C19-C20 bond), which were employed in the attachment of the target side chains. The key building blocks for the total synthesis were thus defined as vinyl iodide 6, alkyne 7, and alkyne 8. Our synthesis illustrates the utility of the modified Negishi coupling for the construction of complex dienes, confirms the proposed stereochemistry of reveromycins and paves the way for the preparation of designed analogues for biological study.
Total synthesis of (-)-reveromycin B
Org Lett 2000 Jan 27;2(2):191-4.PMID:10814279DOI:10.1021/ol991281m.
[structure: see text] The total synthesis of the epidermal growth factor inhibitor Reveromycin B (2) is described. A novel, convergent, and stereoselective reaction sequence was utilized to construct the 5,6-spiroketal system 10 which was converted into the natural product 2 by a 16-step sequence.
Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B
J Org Chem 2001 Apr 6;66(7):2382-93.PMID:11281779DOI:10.1021/jo001646c.
The total synthesis of the epidermal growth factor inhibitor Reveromycin B (2) in 25 linear steps from chiral methylene pyran 13 is described. The key steps involved an inverse electron demand hetero-Diels-Alder reaction between dienophile 13 and diene 12 to construct the 6,6-spiroketal 11 which upon oxidation with dimethyldioxirane and acid catalyzed rearrangement gave the 5,6-spiroketal aldehyde 9. Lithium acetylide addition followed by oxidation/reduction and protective group manipulation provided the Reveromycin B spiroketal core 8 which was converted into the reveromycin A (1) derivative 6 in order to confirm the stereochemistry of the spiroketal segment. Introduction of the C1-C10 side chain began with sequential Wittig reactions to form the C8-C9 and C7-C6 bonds, and a tin mediated asymmetric aldol reaction installed the C4 and C5 stereocenters. The final key steps to the target molecule 2 involved a Stille coupling to introduce the C21-C22 bond, succinoylation, selective deprotection, oxidation, and Wittig condensation to form the final C2-C3 bond. Deprotection was effected by TBAF in DMF to afford Reveromycin B (2) in 72% yield.
Total synthesis of Reveromycin B
Org Lett 1999 Sep 23;1(6):941-4.PMID:10823225DOI:10.1021/ol990884v.
[formula: see text] The stereoselective total synthesis of Reveromycin B (2), a novel polyketide-type antibiotic, has been accomplished.
Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities
J Antibiot (Tokyo) 1992 Sep;45(9):1414-9.PMID:1429226DOI:10.7164/antibiotics.45.1414.
Reveromycins A, B, C and D showed inhibitory activity against EGF-stimulated mitogen response in Balb/MK cells. Furthermore reveromycins A, C and D exhibited morphological reversion of srcts-NRK cells, antiproliferative activity against human tumor cell lines and antifungal activity. The effects of reveromycins A, C and D on eukaryotic cells were closely similar to each other, but those of Reveromycin B were very weak. In vitro studies revealed that reveromycin A is a selective inhibitor of protein synthesis in eukaryotic cells.