Racemomycin E
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| Category | Antibiotics |
| Catalog number | BBF-03068 |
| CAS | 3484-68-2 |
| Molecular Weight | 1015.21 |
| Molecular Formula | C43H82N16O12 |
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Description
Racemomycin E is an N-glycoside antibiotic produced by various bacteria such as Streptomyces lavendulae. It has anti-gram-positive bacteria, negative bacteria, mycobacteria and anti-fungal activity.
Specification
| Synonyms | Streptothricin B; A 53930C |
| IUPAC Name | [(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate |
| Canonical SMILES | C1C(C2C(C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCNC(=O)CC(CCCNC(=O)CC(CCCNC(=O)CC(CCCNC(=O)CC(CCCN)N)N)N)N)N)O |
| InChI | InChI=1S/C43H82N16O12/c44-11-1-6-23(45)16-30(62)51-12-2-7-24(46)17-31(63)52-13-3-8-25(47)18-32(64)53-14-4-9-26(48)19-33(65)54-15-5-10-27(49)20-34(66)56-37-38(67)39(71-42(50)69)29(22-60)70-41(37)59-43-57-35-28(61)21-55-40(68)36(35)58-43/h23-29,35-39,41,60-61,67H,1-22,44-49H2,(H2,50,69)(H,51,62)(H,52,63)(H,53,64)(H,54,65)(H,55,68)(H,56,66)(H2,57,58,59)/t23-,24-,25-,26-,27-,28+,29+,35+,36-,37+,38-,39-,41+/m0/s1 |
| InChI Key | SFBVRPSSMVXTDR-PTESPJIQSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria; fungi |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Cloning of antibiotic-resistance genes in Streptomyces
T Murakami, C Nojiri, H Toyama, E Hayashi, K Katumata, H Anzai, Y Matsuhashi, Y Yamada, K Nagaoka J Antibiot (Tokyo). 1983 Oct;36(10):1305-11. doi: 10.7164/antibiotics.36.1305.
Antibiotic-resistance genes were shotgun cloned from antibiotic-producing Streptomyces sp. using pock-forming plasmids (pSF689 and pSF765), as cloning vectors. Streptomyces chartreusis SF1623 and S. lividans 66 were used as host strains. The ribostamycin (RSM) resistance gene was cloned from S. ribosidificus SF733 DNA (on a 2.3 Md PstI fragment) into both S. chartreusis SF1623 and S. lividans 66, using pSF689 as vector. Kanamycin (KM), novobiocin (NB), destomycin (DM) and racemomycin (RM) resistance genes were cloned from S. kanamyceticus M1164, S. spheroides M1469, S. rimofaciens M1470 and S. lavendulae A249 genomic DNA into S. lividans 66, using pSF765 as vector. Furthermore two types of KM resistance determinants derived from S. kanamyceticus M1164 were cloned using S. lividans 66, the pSF689 vector. The RSM resistance gene showed no homology to plasmid pSF733 of S. ribosidificus SF733, but hybridized to PstI or BclI digested total DNA of S. ribosidificus SF733.
2. Biological activities of racemomycin-B, beta-lysine rich streptothricin antibiotic, the main component of Streptomyces lavendulae OP-2
Y Inamori, H Amino, M Tsuboi, S Yamaguchi, H Tsujibo Chem Pharm Bull (Tokyo). 1990 Aug;38(8):2296-8. doi: 10.1248/cpb.38.2296.
Racemomycin-B (RM-B), the main component of Streptomyces lavendulae OP-2 which is the basis of 50% of the antibiotics produced, is a streptothricin antibiotic which contains three beta-lysine moieties in the molecule. RM-B had antimicrobial activity against plant-pathogenic microorganisms and growth-inhibitory activity against the root of Brassica rapa L. at the concentration of 50 ppm. It strongly inhibited the growth of Pseudomonas syringae pv. tabaci IFO-3508 (minimum inhibitory concentration (MIC): 0.4 microgram/ml), and also showed antifungal activity against six kinds of Fusarium oxysporum species (MIC: 0.1-2.0 micrograms/ml). The antimicrobial activity of RM-B was much stronger than those of RM-A and -C which contain, respectively, one and two beta-lysine moieties in their molecules. The above activities of RM-A, -C and -B were thus in the order of -B greater than -C greater than -A: namely, the biological activity of racemomycin compounds tended to be stronger with increase in the number of beta-lysine moieties in the molecule.
3. The effect of racemomycin-D, a nephrotoxic antibiotic, on cellular metabolism of rat kidney cortex in vitro
Y Inamori, Y Kato, M Kubo, J Nakanishi, M Nakashima, M Gemba Jpn J Pharmacol. 1984 Aug;35(4):397-401. doi: 10.1254/jjp.35.397.
In vitro effects of racemomycin-D on cellular metabolism were examined in rat kidney. Racemomycin-D decreased the concentration gradient of Na+ and K+ across the cell membranes, but failed to influence water content and ATP concentration of kidney cortical slices. The antibiotic inhibited microsomal (Na+ + K+)-ATPase. Preincubation of the microsomes with racemomycin-D enhanced the inhibition about 1.8-fold. Succinoxidase activity of mitochondria remained unaltered in the presence of racemomycin-D, but the antibiotic potently decreased ATP-dependent Ca2+ and Mg2+ uptakes by mitochondria. These results suggest that racemomycin-D probably disorders intracellular homeostasis of Na+, K+ and Ca2+.
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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 ╳
