Dorrigocin B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01171 |
| CAS | 158446-30-1 |
| Molecular Weight | 507.61 |
| Molecular Formula | C27H41NO8 |
Online Inquiry
Description
It is produced by the strain of Streptomyces platensis subsp. rosaceus AB-1981F-75. It has weak anti-tumor cell activity and moderate anti-aspergillus and fusarium activity, but has no effect on yeast. Dorrigocin B has stronger antitumor and antifungal activities than Dorrigocin A. It can restore the morphology of RAS-deformed NIH/3T3 cells from the deformed phenotype to the normal phenotype.
Specification
| IUPAC Name | (2E,6E,8S,9S,10R,11R,12E,14S)-18-(2,6-dioxopiperidin-4-yl)-9,11-dihydroxy-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid |
| Canonical SMILES | CC(C=C(C)C(C(C)C(C(C=CCCC=CC(=O)O)OC)O)O)C(=O)CCCC1CC(=O)NC(=O)C1 |
| InChI | InChI=1S/C27H41NO8/c1-17(21(29)11-9-10-20-15-23(30)28-24(31)16-20)14-18(2)26(34)19(3)27(35)22(36-4)12-7-5-6-8-13-25(32)33/h7-8,12-14,17,19-20,22,26-27,34-35H,5-6,9-11,15-16H2,1-4H3,(H,32,33)(H,28,30,31)/b12-7+,13-8+,18-14+/t17-,19+,22-,26-,27-/m0/s1 |
| InChI Key | YQDJUXPUIRGKNV-NRWIMSPQSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi |
| Solubility | Soluble in Methanol, Ethyl Acetate |
Reference Reading
1. Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds
Jianhua Ju, Si-Kyu Lim, Hui Jiang, Jeong-Woo Seo, Ben Shen J Am Chem Soc. 2005 Aug 31;127(34):11930-1. doi: 10.1021/ja053118u.
Iso-Migrastatin (10) has been shown to be the main natural product of Streptomyces platensis, which undergoes a facile, H2O-mediated rearrangement into dorrigocin A (2), 13-epi-dorrigocin A (11), dorrigocin B (3), and migrastatin (1). Eight new congeners (12-19) of 10 were characterized. They can undergo the same H2O-mediated rearrangement into the corresponding 1, 2, 3, and 11 analogues (20-43) or 1,4-Michael addition with cysteine to afford the corresponding analogues (44-51) of NK30424 A and B (5, 6). This study generated a 47-member library of glutarimide polyketides, setting the stage to investigate the SAR for this family of natural products. These results also established the absolute stereochemistry of 5 and 6 and shed new light into the post-polyketide synthase steps for 10 biosynthesis.
2. Dorrigocins: novel antifungal antibiotics that change the morphology of ras-transformed NIH/3T3 cells to that of normal cells. III. Biological properties and mechanism of action
S Kadam, J B McAlpine J Antibiot (Tokyo). 1994 Aug;47(8):875-80. doi: 10.7164/antibiotics.47.875.
The dorrigocins are unique glutarimide antibiotics which were found to reverse the morphology of ras-transformed NIH/3T3 cells from a transformed phenotype to a normal one. The compounds also inhibited the release of yeast mating pheromone, a-factor. The activity of these compounds was not dependent on inhibition of prenylation or protein synthesis. Dorrigocin A was instead found to inhibit the carboxyl methylation in K-ras transformed cells.
3. Migrastatin and a new compound, isomigrastatin, from Streptomyces platensis
Elaine J Woo, Courtney M Starks, John R Carney, Robert Arslanian, Lawrence Cadapan, Stefan Zavala, Peter Licari J Antibiot (Tokyo). 2002 Feb;55(2):141-6. doi: 10.7164/antibiotics.55.141.
Streptomyces platensis (strain NRRL 18993), a producer of dorrigocins, was shown to produce migrastatin, a cyclic congener of dorrigocin A previously reported from a different organism. Additionally a new compound isomeric to migrastatin, isomigrastatin, was also isolated and its structure was determined to be a cyclic form of dorrigocin B. Both compounds were fully characterized from MS and NMR data. Product titers of both were improved by the addition of XAD-16 resin to the fermentation medium.
Recommended Products
| BBF-02614 | Nystatin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
