13-Deoxycarminomycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00836 |
| CAS | 76034-18-9 |
| Molecular Weight | 499.51 |
| Molecular Formula | C26H29NO9 |
| Purity | ≥95% |
Online Inquiry
Description
13-Deoxycarminomycin, an antineoplastic agent and a bacterial metabolite, is a cytotoxic anthracycline antibiotic produced by Streptomyces peucetius var. carminatus (a biochemical mutant of Streptomyces peucetius var. caesius). It has activity against Gram-positive bacteria, Gram-negative bacteria, tumors and P-388 murine leukemia.
Specification
| Related CAS | 76036-24-3 (monohydrochloride) |
| Synonyms | Antibiotic D 788-11; R 20X; 13-Deoxocarminomycin; (8S)-10α-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-ethyl-7,8,9,10-tetrahydro-1,6,8α,11-tetrahydroxy-5,12-naphthacenedione; 13-Deoxocarminomycin I; (1S,3S)-3-Ethyl-3,5,10,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside; 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-10-((3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-8-ethyl-1,6,8,11-tetrahydroxy-, (8S-cis)-; 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-ethyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8S,10S)- |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-ethyl-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CCC1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)O)N)O |
| InChI | InChI=1S/C26H29NO9/c1-3-26(34)8-12-18(15(9-26)36-16-7-13(27)21(29)10(2)35-16)25(33)20-19(23(12)31)22(30)11-5-4-6-14(28)17(11)24(20)32/h4-6,10,13,15-16,21,28-29,31,33-34H,3,7-9,27H2,1-2H3/t10-,13-,15-,16-,21+,26-/m0/s1 |
| InChI Key | UHYFCDBUKBJSFA-JYFLSIMMSA-N |
Properties
| Appearance | Very Dark Green to Black Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Boiling Point | 713.1±60.0°C at 760 mmHg |
| Melting Point | 171-175°C(dec.) |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Chloroform (Slightly), DMSO (Slightly) |
Reference Reading
1. 13-Deoxycarminomycin, a new biosynthetic anthracycline
G Cassinelli, S Forenza, G Rivola, F Arcamone, A Grein, S Merli, A M Casazza J Nat Prod. 1985 May-Jun;48(3):435-9. doi: 10.1021/np50039a011.
A new antitumor antibiotic, 13-deoxycarminomycin, has been isolated from the anthracycline complex produced by Streptomyces peucetius var. carminatus (ATCC 31502), a biochemical mutant of Streptomyces peucetius var. caesius, the doxorubicin-producing microorganism. The new anthracycline, showing antibacterial and cytotoxic activity in vitro, was found active against P-388 murine leukemia.
2. In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA
M L Dickens, N D Priestley, W R Strohl J Bacteriol. 1997 Apr;179(8):2641-50. doi: 10.1128/jb.179.8.2641-2650.1997.
We recently determined the function of the gene product of Streptomyces sp. strain C5 doxA, a cytochrome P-450-like protein, to be daunorubicin C-14 hydroxylase (M. L. Dickens and W. R. Strohl, J. Bacteriol. 178: 3389-3395, 1996). In the present study, we show that DoxA also catalyzes the hydroxylation of 13-deoxycarminomycin and 13-deoxydaunorubicin to 13-dihydrocarminomycin and 13-dihydrodaunorubicin, respectively, as well as oxidizing the 13-dihydro-anthracyclines to their respective 13-keto forms. The Streptomyces sp. strain C5 dauP gene product also was shown unequivocally to remove the carbomethoxy group of the epsilon-rhodomycinone-glycoside (rhodomycin D) to form 10-carboxy-13-deoxycarminomycin. Additionally, Streptomyces sp. strain C5 DauK was found to methylate the anthracyclines rhodomycin D, 10-carboxy-13-deoxycarminomycin, and 13-deoxy-carminomycin, at the 4-hydroxyl position, indicating a broader substrate specificity than was previously known. The products of Streptomyces sp. strain C5 doxA, dauK, and dauP were sufficient and necessary to confer on Streptomyces lividans TK24 the ability to convert rhodomycin D, the first glycoside in daunorubicin and doxorubicin biosynthesis, to doxorubicin.
3. Functional characterization and transcriptional analysis of a gene cluster governing early and late steps in daunorubicin biosynthesis in Streptomyces peucetius
K Madduri, C R Hutchinson J Bacteriol. 1995 Jul;177(13):3879-84. doi: 10.1128/jb.177.13.3879-3884.1995.
Sequence analysis of the Streptomyces peucetius daunorubicin biosynthetic gene cluster revealed a partial (dnrQ) and two complete (dnrD and dnrP) open reading frames flanking dnrK. Bioconversion experiments showed that DnrD converts aklanonic acid methylester to aklaviketone and that DnrC is a methyltransferase that converts aklanonic acid to aklanonic acid methylester. The deduced dnrP gene product, homologous to known esterases, may catalyze the conversion of 10-carbomethoxy-13-deoxycarminomycin to its 10-carboxy derivative. The dnrKPQS genes may be transcribed as a polycistronic mRNA.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-05862 | Epirubicin | 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 ╳
