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Reveromycin D

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Reveromycin D
Category Enzyme inhibitors
Catalog number BBF-04180
CAS 144860-70-8
Molecular Weight 674.82
Molecular Formula C37H54O11
Purity >95% by HPLC

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Reveromycin D is a bacterial metabolite isolated from Streptomyces. It inhibits EGF-induced mitotic activity in Balb/MK cells and has pH-dependent antifungal activity against Candida albicans.

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Storage Store at -20°C
IUPAC Name (2E,4S,5S,6E,8E)-10-[(2R,3S,6R,8R,10S)-8-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dienyl]-10-(3-carboxypropanoyloxy)-3-methyl-10-pentyl-1,7-dioxaspiro[5.5]undecan-2-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid
Canonical SMILES CCCCCC1(CC(OC2(C1)CCC(C(O2)CC=C(C)C=CC(C(C)C=CC(=O)O)O)C)C=CC(=CC(=O)O)C)OC(=O)CCC(=O)O
InChI InChI=1S/C37H54O11/c1-6-7-8-20-36(48-35(45)18-17-33(41)42)23-29(13-9-26(3)22-34(43)44)46-37(24-36)21-19-28(5)31(47-37)15-11-25(2)10-14-30(38)27(4)12-16-32(39)40/h9-14,16,22,27-31,38H,6-8,15,17-21,23-24H2,1-5H3,(H,39,40)(H,41,42)(H,43,44)/b13-9+,14-10+,16-12+,25-11+,26-22+/t27-,28-,29-,30-,31+,36-,37-/m0/s1
InChI Key LAYXXMUMPHOKOM-RCSQVYJHSA-N
Source Streptomyces sp.
Appearance Tan Lyophilisate
Boiling Point 855.3±65.0°C at 760 mmHg
Density 1.2±0.1 g/cm3
Solubility Soluble in ethanol, methanol, DMF, DMSO
1. Reveromycins, new inhibitors of eukaryotic cell growth. I. Producing organism, fermentation, isolation and physico-chemical properties
S Amano, H Takahashi, K Isono, H Koshino, M Yoshihama, S Shimizu, H Osada, T Kudo J Antibiot (Tokyo) . 1992 Sep;45(9):1409-13. doi: 10.7164/antibiotics.45.1409.
New antibiotics named reveromycins A, B, C and D were isolated as inhibitors of mitogenic activity induced by epidermal growth factor (EGF) in a mouse epidermal keratinocyte. Reveromycins were produced by a soil actinomycete (strain SN-593) which belongs to the genus Streptomyces.
2. Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities
H Takahashi, M Nakakoshi, H Koshino, K Isono, M Yoshihama, R Onose, M Sasaki, H Osada J Antibiot (Tokyo) . 1992 Sep;45(9):1414-9. doi: 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.
3. Reveromycins, new inhibitors of eukaryotic cell growth. III. Structures of reveromycins A, B, C and D
H Takahashi, H Osada, H Koshino, K Isono J Antibiot (Tokyo) . 1992 Sep;45(9):1420-7. doi: 10.7164/antibiotics.45.1420.
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 a varied side chain in the molecule. Determination of their structures by chemical and spectroscopic methods, in particular NMR studies, is described.

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