Sporaricin D
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| Category | Antibiotics |
| Catalog number | BBF-02936 |
| CAS | 68743-81-7 |
| Molecular Weight | 417.50 |
| Molecular Formula | C18H35N5O6 |
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Description
It is an aminoglycoside antibiotic produced by the strain of Saccharopolyspora hirsuta subsp. kobensis KC-6606. It has anti-bacterial and mycobacterium effects, and the antibacterial effect of Sporaricin C is twice as strong as Sporaricin D.
Specification
| Synonyms | 2-Amino-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranosyl)-5-[[(formylamino)acetyl]methylamino]-4-O-methyl-2,3,5-trideoxy-D-allo-inositol; Antibiotic KA-6606IV; D-allo-Inositol, 2-amino-2,3,5-trideoxy-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranosyl)-5-[[(formylamino)acetyl]methylamino]-4-O-methyl-; KA-6606-IV |
| IUPAC Name | N-[(1S,2R,3R,4R,6S)-4-amino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-2-hydroxy-6-methoxycyclohexyl]-2-formamido-N-methylacetamide |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(CC(C(C2O)N(C)C(=O)CNC=O)OC)N)N)N |
| InChI | InChI=1S/C18H35N5O6/c1-9(19)12-5-4-10(20)18(28-12)29-17-11(21)6-13(27-3)15(16(17)26)23(2)14(25)7-22-8-24/h8-13,15-18,26H,4-7,19-21H2,1-3H3,(H,22,24)/t9-,10+,11+,12-,13-,15+,16+,17+,18+/m0/s1 |
| InChI Key | VFIPOZSOMJAAJD-QKRADUSQSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria |
| Boiling Point | 663.4±55.0°C (Predicted) |
| Density | 1.27±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Water, Ethanol |
Reference Reading
1. A new broad-spectrum aminoglycoside antibiotic complex, sporaricin. III. The structures of sporaricins A and B
T Deushi, M Nakayama, I Watanabe, T Mori J Antibiot (Tokyo). 1979 Mar;32(3):187-92. doi: 10.7164/antibiotics.32.187.
The structures of sporaricins A and B have been determined to be 2-amino-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-2,3,5-trideoxy-5-(N-glycyl-N-methyl-amino)-4-O-methyl-D-chiro-inositol and 2-amino-1-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-2,3,5-trideoxy-4-O-methyl-5-methylamino-D-chiro-inositol, respectively.
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 ╳
