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R0654

Sigma-Aldrich

Reveromycin A

solid, suitable for cell culture, BioReagent

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About This Item

Empirical Formula (Hill Notation):
C36H52O11
CAS Number:
134615-37-5
Molecular Weight:
660.79
MDL number:
MFCD00912537
UNSPSC Code:
12352207
PubChem Substance ID:
24899342
NACRES:
NA.76

product name

Reveromycin A, solid

biological source

Streptomyces sp.

Quality Level

200

form

solid

mol wt

660.79 g/mol

packaging

pkg of 100 μg

color

tan

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble
ethyl acetate: soluble
methanol: soluble
soluble

antibiotic activity spectrum

fungi

mode of action

protein synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

[H][C@]1(C\C=C(C)\C=C\[C@H](O)[C@@H](C)\C=C\C(O)=O)O[C@]2(CC[C@@H]1C)CC[C@@](CCCC)(OC(=O)CCC(O)=O)[C@@]([H])(O2)\C=C\C(C)=C\C(O)=O

InChI

1S/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29+,30-,35+,36-/m0/s1

InChI key

ZESGNAJSBDILTB-OXVOKJAASA-N

Biochem/physiol Actions

It is an epidermal growth factor (EGF) and eukaryotic cell growth inhibitor.
Reveromycin A is a polyketide antibiotic from Streptomyces sp. Epidermal growth factor (EGF) inhibitor; apoptosis inducer; G1 phase cell cycle inhibitor having antiproliferative behavior against human cell lines KB and K562 as well as antifungal activity.

Analysis Note

Avoid acidic conditions.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Tanaka et al.
Journal of dental research, 91(8), 771-776 (2012-06-08)
In osteoprotegerin-deficient (OPG-/-) mice, osteoclast activity causes bone resorption to outpace bone formation, leading to the development of severe osteoporosis. Such mice are therefore useful for investigating the alveolar bone of patients with osteoporosis. Reveromycin A (RM-A) was recently identified
H Koshino et al.
The Journal of antibiotics, 45(9), 1420-1427 (1992-09-01)
Reveromycins A, B, C and D are new group inhibitors of the mitogenic activity of epidermal growth factor (EGF), produced by Streptomyces sp. Reveromycins are novel polyketide type antibiotics which have two terminal carboxylic groups, a spiroketal, a succinate and
Shunji Takahashi et al.
Nature chemical biology, 7(7), 461-468 (2011-06-07)
Spiroacetal compounds are ubiquitous in nature, and their stereospecific structures are responsible for diverse pharmaceutical activities. Elucidation of the biosynthetic mechanisms that are involved in spiroacetal formation will open the door to efficient generation of stereospecific structures that are otherwise
Koji Hiraoka et al.
Cancer science, 99(8), 1595-1602 (2008-08-30)
Attention has recently focused on the critical role of inflammatory responses in the tumor stroma that provide favorable conditions for cancer-cell growth and invasion/metastasis. In particular, macrophages recruited into the tumor stroma and activated, known as tumor-associated macrophages, are suggested
Mariana El Sous et al.
Organic letters, 6(17), 3001-3004 (2004-08-28)
The asymmetric total synthesis of (-)-reveromycin A is described. The key steps involved a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the spiroketal core 4 in a highly stereoselective manner and introduction of the
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