Neomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02116 |
| CAS | 119-04-0 |
| Molecular Weight | 614.64 |
| Molecular Formula | C23H46N6O13 |
| Purity | ≥95% |
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Description
Neomycin B is originally isolated from Str. fradiae 3535. It is mainly resistant to bacteria and mycobacteria, and its activity is the strongest of the three components.
Specification
| Related CAS | 1405-10-3 (sulfate salt) |
| Synonyms | Framycetin; Mycifradin; Soframycin; Dekamycin II; O-2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-D-streptamine |
| Storage | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| 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,6S)-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-VCIWKGPPSA-N |
| Source | Streptomyces Fradiae |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 927.1°C at 760 mmHg |
| Melting Point | >194°C (dec.) |
| Density | 1.61 g/cm3 |
| Solubility | Soluble in Aqueous Acid (Slightly), Water (Slightly) |
Reference Reading
1. Characterization of a radical S-adenosyl-L-methionine epimerase, NeoN, in the last step of neomycin B biosynthesis
Shota Hoshi, Tadashi Eguchi, Taiki Kawashima, Fumitaka Kudo, Toshiaki Kamachi J Am Chem Soc . 2014 Oct 1;136(39):13909-15. doi: 10.1021/ja507759f.
The last step of neomycin biosynthesis is the epimerization at C-5‴ of neomycin C to give neomycin B. A candidate enzyme responsible for the epimerization was a putative radical S-adenosyl-L-methionine (SAM) enzyme, NeoN, which is uniquely encoded in the neomycin biosynthetic gene cluster and remained an unassigned protein in the neomycin biosynthesis. The reconstituted and reduced NeoN showed the expected epimerization activity in the presence of SAM. In the epimerization, 1 equiv of SAM was consumed to convert neomycin C into neomycin B. The site of neomycin C reactive toward epimerization was clearly confirmed to be C-5‴ by detecting the incorporation of a deuterium atom from the deuterium oxide-based buffer solution. Further, alanine scanning of the NeoN cysteine residues revealed that C249 is a critical amino acid residue that provides a hydrogen atom to complete the epimerization. Furthermore, electron paramagnetic resonance analysis of the C249A variant in the presence of SAM and neomycin C revealed that a radical intermediate is generated at the C-5‴ of neomycin C. Therefore, the present study clearly illustrates that the epimerization of neomycin C to neomycin B is catalyzed by a unique radical SAM epimerase NeoN with a radical reaction mechanism.
2. Synthesis and antibacterial activity of amphiphilic lysine-ligated neomycin B conjugates
George G Zhanel, Smritilekha Bera, Frank Schweizer Carbohydr Res . 2011 Apr 1;346(5):560-8. doi: 10.1016/j.carres.2011.01.015.
Amphiphilic lysine-ligated neomycin B building blocks were prepared by reductive amination of a protected C5″-modified neomycin B-based aldehyde and side chain-unprotected lysine or lysine-containing peptides. It was demonstrated that a suitably protected lysine-ligated neomycin B conjugate (NeoK) serves as a building block for peptide synthesis, enabling incorporation of aminoglycoside binding sites into peptides. Antibacterial testing of three amphiphilic lysine-ligated neomycin B conjugates against a representative panel of Gram-positive and Gram-negative strains demonstrates that C5″-modified neomycin-lysine conjugate retains antibacterial activity. However, in most cases the lysine-ligated neomycin B analogs display reduced potency against Gram-positive strains when compared to unmodified neomycin B or unligated peptide. An exception is MRSA where an eightfold enhancement was observed. When compared to unmodified neomycin B, the prepared lysine-neomycin conjugates exhibited a 4-8-fold enhanced Gram-negative activity against Pseudomonas aeruginosa and up to 12-fold enhanced activity was observed when compared to unligated reference peptides.
3. [Synthesis of biomimetic analogs of neomycin B]
Naozumi Nishizono Yakugaku Zasshi . 2002 Jul;122(7):465-9. doi: 10.1248/yakushi.122.465.
Neomycin B has been found to block the binding of HIV-1 Rev protein to its viral RNA recognition site, thereby inhibiting the production of the virus. This paper describes the synthesis of analogues of neomycin B, which are potential anti-HIV compounds designed as inhibitors of Rev/RRE binding.
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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 ╳
