Sporaricin B
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| Category | Antibiotics |
| Catalog number | BBF-02934 |
| CAS | 68743-78-2 |
| Molecular Weight | 332.44 |
| Molecular Formula | C15H32N4O4 |
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Description
It is an aminoglycoside antibiotic produced by the strain of Saccharopolyspora hirsuta subsp. kobensis KC-6606. It mainly has the effect of anti-Gram-positive bacteria. The antibacterial activity of Sporaricin A is 8-60 times stronger than Sporaricin B.
Specification
| Synonyms | Antibiotic KA 6606II; KA 6606II; D-allo-Inositol, 2-amino-2,3,5-trideoxy-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-4-O-methyl-5-(methylamino)-; 2-Amino-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranosyl)-4-O-methyl-5-methylamino-2,3,5-trideoxy-D-allo-inositol; 2-Deoxyfortimycin B |
| IUPAC Name | (1R,2R,3R,5S,6S)-3-amino-2-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-5-methoxy-6-(methylamino)cyclohexan-1-ol |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(CC(C(C2O)NC)OC)N)N)N |
| InChI | InChI=1S/C15H32N4O4/c1-7(16)10-5-4-8(17)15(22-10)23-14-9(18)6-11(21-3)12(19-2)13(14)20/h7-15,19-20H,4-6,16-18H2,1-3H3/t7-,8+,9+,10-,11-,12+,13+,14+,15+/m0/s1 |
| InChI Key | YGRYQFMCQIZSDG-SSHYVVCRSA-N |
Properties
| Appearance | Colorless Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 490.1±45.0°C (Predicted) |
| Density | 1.19±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Water |
Reference Reading
1. In vitro and in vivo antibacterial activities of K-4619, a new semisynthetic aminoglycoside
Y Saino, Y Hattori, T Koshi, F Kobayashi, T Oda, S Mitsuhashi Antimicrob Agents Chemother. 1984 Aug;26(2):187-91. doi: 10.1128/AAC.26.2.187.
The antibacterial activities of K-4619 (3-de-O-methylsporaricin A sulfate) were compared with those of sporaricin A, amikacin, dibekacin, and gentamicin. K-4619 exhibited a high order of activity against gram-positive and gram-negative bacteria, including Pseudomonas aeruginosa. Its activity against Providencia species and Serratia marcescens was the highest of all drugs tested. K-4619 was highly effective against bacteria that produce various aminoglycoside-inactivating enzymes, except for 3-acetyltransferase I. The bactericidal activity of K-4619 was somewhat greater than that of amikacin. The activity of K-4619 against gram-negative bacteria increased at alkaline pH and was hardly affected by inoculum size, addition of horse serum, and composition of the medium. The in vivo protective effect of K-4619 against infections with Klebsiella pneumoniae, S. marcescens, and P. aeruginosa in mice was greater than that of sporaricin A. K-4619 was also active in mice infected with gentamicin- or amikacin-resistant strains bearing some of the aminoglycoside-inactivating enzymes.
2. A new broad-spectrum aminoglycoside antibiotic complex, sporaricin. IV. Sporaricins C and D
T Deushi, I Watanabe, A Iwasaki, K Kamiya, T Mizoguchi, M Nakayama, M Okuchi, H Itoh, T Mori J Antibiot (Tokyo). 1981 Jul;34(7):811-7. doi: 10.7164/antibiotics.34.811.
Two new aminoglycoside antibiotics, sporaricins C and D have been isolated from the culture broth of Saccharopolyspora hirsuta subsp. kobensis, which produced sporaricins A and B. The structures of sporaricins C and D have been determined to be 4-N-carbamoyl-glycylsporaricin B and 4-N-formylglycylsporaricin B, respectively. Sporaricins C and D are active against Gram-negative and Gram-negative bacteria including aminoglycoside-resistant strains.
3. Total synthesis of 3-O-demethylsporaricin A
N Yasuda, K Matsuda, H Tsutsumi, T Takaya J Antibiot (Tokyo). 1985 Nov;38(11):1512-25. doi: 10.7164/antibiotics.38.1512.
The novel, semisynthetic pseudodisaccharide antibiotic, 3-O-demethylsporaricin A, was synthesized via 3-O-demethylsporaricin B obtained by glycosidation of its aminocyclitol part. The aminocyclitol part was synthesized as D,L-form from D,L-(1,2,3/4,5,6)-1,4-bis(benzyloxy-carbonylamino)-5,6-O-isopropyl idene-2,3,5,6-cyclohexanetetraol via three key steps, namely, deoxygenation, inversion of a hydroxyl group, and N-methylation. The physical and biological properties of synthetic 3-O-demethylsporaricin A and an authentic sample derived from sporaricin B were identical.
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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 ╳
