Verdamycin
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| Category | Antibiotics |
| Catalog number | BBF-02745 |
| CAS | 49863-48-1 |
| Molecular Weight | 461.55 |
| Molecular Formula | C20H39N5O7 |
| Purity | 98% |
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Description
It is produced by the strain of Micromonospora grisea. Verdamycin has anti-bacterial effect. In in vivo test of mice, it has protective effect on the infection of Escherichia coli, Pseudomonas aeruginosa and Staphylococcus.
Specification
| Synonyms | Verdamicin; O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6-)-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-threo-hept-4-enopyranosyl-(1-4))-2-deoxy-D-streptamine |
| IUPAC Name | (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-[(1S)-1-aminoethyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CC(C1=CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)N |
| InChI | InChI=1S/C20H39N5O7/c1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19/h5,8-11,13-19,25-28H,4,6-7,21-24H2,1-3H3/t8-,9+,10-,11+,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1 |
| InChI Key | XUSXOPRDIDWMFO-CTMSJIKGSA-N |
Properties
| Boiling Point | 677.3°C at 760 mmHg |
| Density | 1.36 g/cm3 |
Reference Reading
1. Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans
Stephen Hanessian, Janek Szychowski, J Pablo Maianti Org Lett. 2009 Jan 15;11(2):429-32. doi: 10.1021/ol802421d.
A synthesis of verdamicin C2 and its congener C2a has been accomplished from sisomicin relying on a novel oxidative transformation of an allylic azide to the corresponding alpha,beta-unsaturated aldehyde, and its stereocontrolled elaboration into the intended 5' side chain of verdamicin C2 and C2a. In vitro antibacterial testing shows that both C6' epimers in verdamicin C2 and C2a are equally active against a variety of bacterial strains. Oxidation of allylic primary azides, ethers, and esters of 2-substituted dihydro[2H]pyrans with SeO(2) leads directly to the corresponding aldehydes.
2. In vivo antibacterial activity of vertilmicin, a new aminoglycoside antibiotic
Xue-Fu You, Cong-Ran Li, Xin-Yi Yang, Min Yuan, Wei-Xin Zhang, Ren-Hui Lou, Yue-Ming Wang, Guo-Qing Li, Hui-Zhen Chen, Dan-Qing Song, Cheng-Hang Sun, Shan Cen, Li-Yan Yu, Li-Xun Zhao, Jian-Dong Jiang Antimicrob Agents Chemother. 2009 Oct;53(10):4525-8. doi: 10.1128/AAC.00223-09. Epub 2009 Jul 27.
Vertilmicin is a novel aminoglycoside antibiotic with potent activity against gram-negative and -positive bacteria in vitro. In this study, we further evaluated the efficacy of vertilmicin in vivo in systemic and local infection animal models. We demonstrated that vertilmicin had relatively high and broad-spectrum activities against mouse systemic infections caused by Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, and Enterococcus faecalis. The 50% effective doses of subcutaneously administered vertilmicin were 0.63 to 0.82 mg/kg, 0.18 to 0.29 mg/kg, 0.25 to 0.99 mg/kg, and 4.35 to 7.11 mg/kg against E. coli, K. pneumoniae, S. aureus, and E. faecalis infections, respectively. The therapeutic efficacy of vertilmicin was generally similar to that of netimicin, better than that of gentamicin in all the isolates tested, and better than that of verdamicin against E. coli 9612 and E. faecalis HH22 infections. The therapeutic efficacy of vertilmicin was further confirmed in local infection models of rabbit skin burn infection and mouse ascending urinary tract infection.
3. The bifunctional enzyme, GenB4, catalyzes the last step of gentamicin 3',4'-di-deoxygenation via reduction and transamination activities
Xiaotang Chen, Hui Zhang, Shaotong Zhou, Mingjun Bi, Shizhou Qi, Huiyuan Gao, Xianpu Ni, Huanzhang Xia Microb Cell Fact. 2020 Mar 10;19(1):62. doi: 10.1186/s12934-020-01317-0.
Background: New semi-synthetic aminoglycoside antibiotics generally use chemical modifications to avoid inactivity from pathogens. One of the most used modifications is 3',4'-di-deoxygenation, which imitates the structure of gentamicin. However, the mechanism of di-deoxygenation has not been clearly elucidated. Results: Here, we report that the bifunctional enzyme, GenB4, catalyzes the last step of gentamicin 3',4'-di-deoxygenation via reduction and transamination activities. Following disruption of genB4 in wild-type M. echinospora, its products accumulated in 6'-deamino-6'-oxoverdamicin (1), verdamicin C2a (2), and its epimer, verdamicin C2 (3). Following disruption of genB4 in M. echinospora ΔgenK, its products accumulated in sisomicin (4) and 6'-N-methylsisomicin (5, G-52). Following in vitro catalytic reactions, GenB4 transformed sisomicin (4) to gentamicin C1a (9) and transformed verdamicin C2a (2) and its epimer, verdamicin C2 (3), to gentamicin C2a (11) and gentamicin C2 (12), respectively. Conclusion: This finding indicated that in addition to its transamination activity, GenB4 exhibits specific 4',5' double-bond reducing activity and is responsible for the last step of gentamicin 3',4'-di-deoxygenation. Taken together, we propose three new intermediates that may refine and supplement the specific biosynthetic pathway of gentamicin C components and lay the foundation for the complete elucidation of di-deoxygenation mechanisms.
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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 ╳
