Gentamicin C1a
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| Category | Antibiotics |
| Catalog number | BBF-04434 |
| CAS | 26098-04-4 |
| Molecular Weight | 449.54 |
| Molecular Formula | C19H39N5O7 |
| Purity | ≥95.0% |
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Description
It is a broad-spectrum aminoglycoside antibiotic produced by the strain of Micromonospora spp. One of several components of the gentamicin C complex which comprises approximately 80% gentamicin and exhibits the most potent antimicrobial activity.
Specification
| Related CAS | 37713-04-5 (sulfate salt) |
| Synonyms | Gentamycin C1A; Gentamycin C12; O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-2-deoxy-D-streptamine |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O |
| InChI | InChI=1S/C19H39N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1 |
| InChI Key | VEGXETMJINRLTH-BOZYPMBZSA-N |
| Source | Micromonospora |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 675.2±55.0°C (Predicted) |
| Melting Point | 102-108°C |
| Density | 1.36±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Dimethylformamide, Pyridine, Water |
Reference Reading
1. Dissociating antibacterial from ototoxic effects of gentamicin C-subtypes
Alan G Cheng, Adela Perez, Zehra Siddiqui, Kate Comstock, Robert Greenhouse, Yohan Song, Dennis Lagasca, Patrick J Atkinson, Markus E Huth, Randy Lin, Jacob P MacDonald, Mary E O'Sullivan, Anthony J Ricci Proc Natl Acad Sci U S A . 2020 Dec 22;117(51):32423-32432. doi: 10.1073/pnas.2013065117.
Gentamicin is a potent broad-spectrum aminoglycoside antibiotic whose use is hampered by ototoxic side-effects. Hospital gentamicin is a mixture of five gentamicin C-subtypes and several impurities of various ranges of nonexact concentrations. We developed a purification strategy enabling assaying of individual C-subtypes and impurities for ototoxicity and antimicrobial activity. We found that C-subtypes displayed broad and potent in vitro antimicrobial activities comparable to the hospital gentamicin mixture. In contrast, they showed different degrees of ototoxicity in cochlear explants, with gentamicin C2b being the least and gentamicin C2 the most ototoxic. Structure-activity relationships identified sites in the C4'-C6' region on ring I that reduced ototoxicity while preserving antimicrobial activity, thus identifying targets for future drug design and mechanisms for hair cell toxicity. Structure-activity relationship data suggested and electrophysiological data showed that the C-subtypes both bind and permeate the hair cell mechanotransducer channel, with the stronger the binding the less ototoxic the compound. Finally, both individual and reformulated mixtures of C-subtypes demonstrated decreased ototoxicity while maintaining antimicrobial activity, thereby serving as a proof-of-concept of drug reformulation to minimizing ototoxicity of gentamicin in patients.
2. Synthesis of Gentamicin Minor Components: Gentamicin C1a and Gentamicin C2b
Santanu Jana, David Crich Org Lett . 2022 Nov 25;24(46):8564-8567. doi: 10.1021/acs.orglett.2c03616.
Gentamicin C1a and the minor isomer C2b have been reported to have favorable properties in terms of antibacterial activity and toxicity compared to the commercial mixture from which they have previously been isolated by preparative high-performance liquid chromatography. We report straightforward syntheses of both compounds from readily available sisomicin by selective oxidation of the side chain in ring I, hydrogenation of the double bond in ring I to give the 5'-epi series, inversion of configuration at position 5' under thermodynamic conditions, and installation of the 6'-amino group by reductive amination.
3. Engineering the methyltransferase through inactivation of the genK and genL leads to a significant increase of gentamicin C1a production in an industrial strain of Micromonospora echinospora 49-92S
Feng Xu, Xinyu Zhang, Xiwei Tian, Jie Wu, Xiang Ke, Ling Liu, Yuanxin Guo, Ju Chu Bioprocess Biosyst Eng . 2022 Oct;45(10):1693-1703. doi: 10.1007/s00449-022-02774-0.
In this study, a single-component high-yielding Micromonospora echinospora strain 49-92S-KL01 was constructed by deleting methyltransferase-encoding genes genK and genL. In 5-L fermentation trials, gentamicin C1a titers in the mutant strain were 3.22-fold higher than that in the parental strain (211 U/mL vs. 50 U/mL). The glycolysis pathway and tricarboxylic acid cycle fluxes were reduced by 26.8% and 26.6%, respectively, compared to the parental strain according to the metabolic flux analysis during the stationary phase, resulting in lower levels of energy supplements required for the cellular maintenance. Meanwhile, a significant enhancement in precursor (paromamine) accumulation and availability was observed in 49-92S-KL01 compared to parental strain. These results indicate that genK and genL significantly affect the synthesis of gentamicin C1a. In addition, this study provides a more rational strategy for gentamicin C1a production.
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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 ╳
