Kinamycin B
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| Category | Antibiotics |
| Catalog number | BBF-01547 |
| CAS | 35303-13-0 |
| Molecular Weight | 412.35 |
| Molecular Formula | C20H16N2O8 |
| Purity | >98% |
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Description
Kinamycin B is produced by the strain of Str. murayamaensis. Kinamycin B has antibacterial and mycobacterial effects, but it has weak activity against gram-negative bacteria.
Specification
| Synonyms | BRN 0503790; (1R,2R,3R,4S)-2-acetyloxy-11-diazonio-1,3,4,10-tetrahydroxy-2-methyl-9-oxo-3,4-dihydro-1H-benzo[b]fluoren-5-olate |
| IUPAC Name | [(1R,2R,3R,4S)-11-diazo-1,3,4,9-tetrahydroxy-2-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[b]fluoren-2-yl] acetate |
| Canonical SMILES | CC(=O)OC1(C(C(C2=C(C1O)C(=[N+]=[N-])C3=C2C(=O)C4=C(C3=O)C(=CC=C4)O)O)O)C |
| InChI | InChI=1S/C20H16N2O8/c1-6(23)30-20(2)18(28)13-11(17(27)19(20)29)10-12(14(13)22-21)16(26)9-7(15(10)25)4-3-5-8(9)24/h3-5,17-19,24,27-29H,1-2H3/t17-,18+,19+,20+/m0/s1 |
| InChI Key | UZCOWBDCSCNWHJ-MTQWCTHYSA-N |
Properties
| Appearance | Orange Acicular Crystalline |
| Antibiotic Activity Spectrum | mycobacteria; Gram-negative bacteria |
| Melting Point | 190-193°C |
Reference Reading
1. Crystal structure of AlpK: An essential monooxygenase involved in the biosynthesis of kinamycin
Wenpeng Wang, Jun Li, HuanHuan Li, Keqing Fan, Yingfang Liu Biochem Biophys Res Commun. 2019 Mar 19;510(4):601-605. doi: 10.1016/j.bbrc.2019.01.077. Epub 2019 Feb 7.
AlpK is an essential monooxygenase involved in the biosynthesis of kinamycin. It catalyzes the C5-hyfroxylattion of the crucial benzo[b]-fluorence intermediate in kinamycin synthesis. However, the structure and mechanism of AlpK is unclear. Here, we report the first structure of AlpK in complex with FAD. Our structure sheds light on the catalytic mechanism of AlpK.
2. Inactivation of Flavoenzyme-Encoding Gene flsO1 in Fluostatin Biosynthesis Leads to Diversified Angucyclinone Derivatives
Chunfang Yang, Chunshuai Huang, Chunyan Fang, Liping Zhang, Siqiang Chen, Qingbo Zhang, Changsheng Zhang, Wenjun Zhang J Org Chem. 2021 Aug 20;86(16):11019-11028. doi: 10.1021/acs.joc.0c02517. Epub 2021 Feb 3.
Inactivation of the flavoenzyme-encoding gene flsO1 in fluostatin biosynthesis led to the isolation of four new angucyclinone derivatives (11, 12, 14, and 15), among which fluostarenes A (14) and B (15) featured the unprecedented 6/6/5/6/6 pentacyclic skeleton with fusion of a benzo[b]fluorene and a six-membered lactone ring. Both 14 and 15 were putatively generated via quinone methide-mediated nonenzymatic reactions. Fluostarene B (15) exhibited cytotoxicity against several cancer cell lines with IC50 values ranging from 7 to 10 μM. Fluostarenes A (14), B (15), and PK1 (16) showed α-glucosidase inhibition activity with IC50 of 0.89, 1.58, and 0.13 μM, respectively. Successful complementation of the ΔflsO1 mutant with alpK from kinamycin biosynthesis suggests that FlsO1 should function equivalently to AlpK as a putative C-5 hydroxylase.
3. Kinamycin biosynthesis employs a conserved pair of oxidases for B-ring contraction
Bin Wang, Jinwei Ren, Liyuan Li, Fang Guo, Guohui Pan, Guomin Ai, Bertrand Aigle, Keqiang Fan, Keqian Yang Chem Commun (Camb). 2015 May 25;51(42):8845-8. doi: 10.1039/c5cc01986a.
The biosynthesis of diazobenzofluorene kinamycins requires a hitherto uncharacterized B-ring contraction. Via detailed genetic and enzymatic analyses we unambiguously characterized the conserved pairs of oxidases, AlpJ and AlpK homologs, as nature's machinery for benzofluorenone formation, which paves the way for the investigation of the following diazo assembly.
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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 ╳
