Sannamycin J
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| Category | Antibiotics |
| Catalog number | BBF-02874 |
| CAS | 83997-42-6 |
| Molecular Weight | 318.41 |
| Molecular Formula | C14H30N4O4 |
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Description
It is an aminoglycoside antibiotic produced by the strain of Str. sannanensis sp. nov. It has weak antibacterial activity against Gram-positive bacteria and Gram-negative bacteria.
Specification
| Synonyms | 5-Amino-6-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl)-3-O-methyl-2-(methylamino)-2,4,5-trideoxy-D-epi-inositol; Antibiotic KA-7038IX; KA-7038IX |
| IUPAC Name | (1R,2R,3S,5R,6S)-3-amino-2-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-5-methoxy-6-(methylamino)cyclohexan-1-ol |
| Canonical SMILES | CNC1C(CC(C(C1O)OC2C(CCC(O2)CN)N)N)OC |
| InChI | InChI=1S/C14H30N4O4/c1-18-11-10(20-2)5-9(17)13(12(11)19)22-14-8(16)4-3-7(6-15)21-14/h7-14,18-19H,3-6,15-17H2,1-2H3/t7-,8+,9-,10+,11+,12+,13+,14+/m0/s1 |
| InChI Key | LVWCJJGPEHPHJN-ZRXDKONOSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Solubility | Soluble in Methanol, Water |
Reference Reading
1. A new aminoglycoside antibiotic, sannamycin C and its 4-N-glycyl derivative
T Deushi, T Yamaguchi, K Kamiya, A Iwasaki, T Mizoguchi, M Nakayama, I Watanabe, H Itoh, T Mori J Antibiot (Tokyo). 1980 Nov;33(11):1274-80. doi: 10.7164/antibiotics.33.1274.
Streptomyces sannanensis KC-7038 used for the production of sannamycins A and B has also produced another antibiotic sannamycin C, in the culture broth. Physico-chemical characterization revealed that sannamycin C is a new aminoglycoside antibiotic having 6-N-methylpurpurosamine C and 2-deoxy-3-epi-fortamine. Its 4-N-glycyl derivative indicated inhibitory activity against Gram-positive and Gram-negative bacteria containing aminoglycoside resistant strains.
2. Cloning and analysis of a gene (sms13) encoding sannamycin B-glycyltransferase from Streptomyces sannanensis and its distribution among actinomycetes
T Ohta, E Hashimoto, M Hasegawa J Antibiot (Tokyo). 1992 Jul;45(7):1167-75. doi: 10.7164/antibiotics.45.1167.
A gene encoding sannamycin B-glycyltransferase (sms13) of Streptomyces sannanensis IFO 14239 was identified by cloning and complementation of S. sannanensis mutant SN13 which is blocked at the interconversion of sannamycins B and A. The cloned DNA fragment also permitted the conversion of fortimicin B to A both in S. sannanensis SN13 and Streptomyces lividans TK23. DNA sequences similar to sms13 were detected in all five producers of the fortimicin-group antibiotics, Micromonospora olivasterospora ATCC 21819 (fortimicin-producer), Micromonospora sp. strain SF-2098 ATCC 31580 (SF-2052), Dactylosporangium matsuzakiense ATCC 31570 (dactimicin), Streptomyces tenjimariensis ATCC 31603 (istamycin), and Saccharopolyspora hirsuta ATCC 20501 (sporaricin). This suggests that these genes of similar function from different genera were derived from a common ancestral gene.
3. Characterization of two different types of resistance genes among producers of fortimicin-group antibiotics
T Ohta, T Dairi, M Hasegawa J Gen Microbiol. 1993 Mar;139(3):591-9. doi: 10.1099/00221287-139-3-591.
Fortimicin-A (FTM-A; astromicin)-resistance genes (fmr genes) isolated from six producers of the FTM-group of antibiotics were analysed. These genes could be classified into two types by the resistance profiles to aminoglycoside antibiotics and by their DNA homologies. Three genes, fmrT from the istamycin producer Streptomyces tenjimariensis ATCC 31603, fmrS from the sannamycin producer Streptomyces sannanensis IFO 14239 and fmrH from the sporaricin producer Saccharopolyspora hirsuta ATCC 20501, conferred resistance to FTM-A, kanamycin (Km) and neomycin B (Nm-B), but not to gentamicin (Gm). The other three genes, fmrO from the FTM-A producer Micromonospora olivasterospora ATCC 21819, fmrM from the antibiotic SF-2052 producer Micromonospora sp. SF-2098 (ATCC 31580) and fmrD from the dactimicin producer Dactylosporangium matsuzakiense ATCC 31570, conferred resistance to FTM-A, Km and Gm, but not to Nm-B. No DNA homology was detected between the two types of the resistance genes in Southern-blot analysis. The present results revealed that, in spite of the similarity of their biosynthesis genes, there are at least two different types of resistance genes among the FTM-group antibiotic producers.
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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 ╳
