Epelmycin D
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| Category | Antibiotics |
| Catalog number | BBF-01239 |
| CAS | 107807-22-7 |
| Molecular Weight | 585.60 |
| Molecular Formula | C30H35NO11 |
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Description
It is produced by the strain of Streptomyces violaceus A262. It has anti-gram positive, negative bacteria and candida albicans activity, and has anti-leukemic L1210 activity, which is stronger than Aclacinomycin.
Specification
| Synonyms | Violamycin A4; 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7,12-tetrahydroxy-6,11-dioxo-4-((2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, methyl ester |
| IUPAC Name | methyl (1R,2S,4R)-4-[(2S,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| Canonical SMILES | CCC1(CC(C2=C(C1C(=O)OC)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)O)N(C)C)O |
| InChI | InChI=1S/C30H35NO11/c1-6-30(39)11-16(42-17-10-14(31(3)4)24(33)12(2)41-17)19-20(23(30)29(38)40-5)28(37)21-22(27(19)36)26(35)18-13(25(21)34)8-7-9-15(18)32/h7-9,12,14,16-17,23-24,32-33,36-37,39H,6,10-11H2,1-5H3/t12-,14-,16+,17+,23-,24+,30-/m0/s1 |
| InChI Key | CVACSAHKWDLUII-BXTJAPIWSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Yeast |
| Boiling Point | 701.2 °C at 760 mmHg |
| Melting Point | 152-154 °C |
| Density | 1.50 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Anthracycline metabolites from Streptomyces violaceus A262. II. New anthracycline epelmycins produced by a blocked mutant strain SU2-730
O Johdo, Y Watanabe, T Ishikura, A Yoshimoto, H Naganawa, T Sawa, T Takeuchi J Antibiot (Tokyo). 1991 Oct;44(10):1121-9. doi: 10.7164/antibiotics.44.1121.
New anthracycline antibiotics, identified as epsilon-rhodomycinone glycosides, were isolated from the culture broth of a blocked mutant of beta-rhodomycin-producing Streptomyces violaceus A262. They were designated as epelmycins A, B, C, D and E, and assayed for their in vitro cytotoxicities against murine leukemic L1210 cell culture and the antimicrobial activities in comparison with known anthracycline antibiotics.
2. Production of a new hybrid anthracycline 4-O-methylepelmycin by heterologous expression of dnrK in epelmycin-producing Streptomyces violaceus
Y Miyamoto, S Ohta, O Johdo, Y Nagamatsu, A Yoshimoto J Antibiot (Tokyo). 2000 Aug;53(8):828-36. doi: 10.7164/antibiotics.53.828.
A new hybrid anthracycline antibiotic was produced by heterologous expression of dnrK encoding carminomycin 4-O-metyltransferase in an epelmycin-producing Streptomyces violaceus. pMK100 was constructed by insertion of Steptomyces peucetius dnrK gene in Steptomyces-expression vector pIJ6021 and introduced to the epelmycin producer. The transformant produced a hybrid anthracycline antibiotic together with host epelmycins when cultured in antibiotic production medium in the presence of thiostrepton. The hybrid anthracycline was determined to be 7-O-L-rhodosaminyl-4-O-methyl-epsilon-rhodomycinone (4-O-methylepelmycin D). However, the attempts on production of hybrid 4-O-methylaclarubicin and 4-O-methyl-1-deoxyobelmycin by the transformants of aclarubicin and 1-deoxyobelmycin producers with pMK 100 were unsuccessful.
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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 ╳
