Neomycin C
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| Category | Antibiotics |
| Catalog number | BBF-02117 |
| CAS | 66-86-4 |
| Molecular Weight | 614.64 |
| Molecular Formula | C23H46N6O13 |
| Purity | 99% |
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Description
Neomycin C is originally isolated from Str. fradiae 3535. It is mainly resistant to bacteria and mycobacteria.
Specification
| Related CAS | 63121-20-0 (mono-hydrochloride) |
| Synonyms | (1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N |
| InChI | InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1 |
| InChI Key | PGBHMTALBVVCIT-VZXHOKRSSA-N |
| Source | Streptomyces Fradiae |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 927.1°C at 760 mmHg |
| Melting Point | >113°C (dec.) |
Reference Reading
1. Antimicrobial activity of neomycin C against Staphylococcus epidermidis
R Baas, K Tsuji, J H Robertson, R L Yeager Appl Microbiol . 1971 Dec;22(6):1164-5. doi: 10.1128/am.22.6.1164-1165.1971.
In vitro studies indicate that neomycin C is 50% as active as neomycin B against Staphylococcus epidermidis (ATCC 12228).
2. Component Optimization of Neomycin Biosynthesis via the Reconstitution of a Combinatorial Mini-Gene-Cluster in Streptomyces fradiae
Jihui Zhang, Hanye Guan, Junyue Li, Huarong Tan, Yue Li, Dong Li, Jiazhen Zheng ACS Synth Biol . 2020 Sep 18;9(9):2493-2501. doi: 10.1021/acssynbio.0c00281.
Neomycin, a multicomponent aminoglycoside antibiotic, is mainly utilized in livestock husbandry and feed additives in animals. The antimicrobial potency of the main product neomycin B is higher than that of its stereoisomer neomycin C. However, the content of neomycin C as an impurity in the high-producing strain is relatively high, and its isolation or removal from neomycin B is quite difficult, which influences the widespread application of neomycin. In this work, the essential genes responsible for neomycin biosynthesis were evaluated and overexpressed to reduce the content of neomycin C. Among them,neoGandneoHare two novel regulatory genes for neomycin biosynthesis,aphAis a resistance gene,neoNencoding a radical SAM-dependent epimerase is responsible for the conversion of neomycin C to B using SAM as the cofactor, andmetKis a SAM synthetase coding gene. We demonstrated that the reconstitution and overexpression of a mini-gene-cluster (PkasO*-neoN-metK-PkasO*-neoGH-aphA) could effectively reduce the accumulation of neomycin C from 19.1 to 12.7% and simultaneously increase neomycin B by ~13.1% in the engineered strain Sf/pKCZ04 compared with the wild-type strain (Sf). Real-time quantitative polymerase chain reaction analysis revealed the remarkable up-regulation of theneoE,neoH,neoN, andmetKgenes situated in the mini-gene-cluster. The findings will pave a new path for component optimization and the large-scale industrial production of significant commercial antibiotics.
3. Neomycin: microbiological assay or liquid chromatography?
E Adams, P Louis, S Rico, E Roets, K Dierick, L Liu, P Nabet, S Guyomard, J Hoogmartens J Pharm Biomed Anal . 1998 Aug;17(4-5):757-66. doi: 10.1016/s0731-7085(97)00247-1.
In a multicentre study involving six laboratories, a microbiological assay was performed on three neomycin samples containing respectively, 0.12, 2.1 and 11% (m/m) of neomycin C, as well on a pure neomycin C sample. The potency was determined according to the European Pharmacopoeia method but using a neomycin B base standard. The relative standard deviations between laboratories (RSD) on the potencies varied from 4.8 to 50%, depending on the sample examined. The RSD increased with the neomycin C content of the samples and the highest RSD values were observed for the pure neomycin C sample. The activity of neomycin C relative to neomycin B was found to be 62% by diffusion (RSD:41%) and 56% by turbidimetry (RSD: 50%). This confirmed that the presence of neomycin C in a neomycin sample influences the reproducibility of the microbiological assay. T estimate the influence of this effect on official standard, their composition was verified by liquid chromatography. The neomycin C base content of the standards varied between 0.4 and 5.8% (m/m). Based on the results obtained and on formerly published reports discussing problems encountered with microbiological assay of neomycin, it is proposed to introduce liquid chromatography in official monographs to replace microbiological assay.
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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 ╳
