Racemomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02169 |
| CAS | 3776-37-2 |
| Molecular Weight | 758.86 |
| Molecular Formula | C31H58N12O10 |
| Purity | >98% |
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Description
It is produced by the strain of Str. racemochromogenes 229. It has broad spectrum antibacterial activity and antifungal effect, and it can inhibit PR-8 of influenza virus in tissue culture.
Specification
| Synonyms | Streptothricin D; Antibiotic OP 2C; 2-{[(3S)-3-amino-6-{[(3S)-3-amino-6-{[(3S)-3,6-diaminohexanoyl]amino}hexanoyl]amino}hexanoyl]amino}-4-O-carbamoyl-2-deoxy-N-[(3aS,7R,7aS)-7-hydroxy-4-oxooctahydro-2H-imidazo[4,5-c]pyridin-2-ylidene]-beta-D-gulopyranosylamine |
| Storage | Store at -20°C |
| 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)-3,6-diaminohexanoyl]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(CCCN)N)N)N)O |
| InChI | InChI=1S/C31H58N12O10/c32-7-1-4-15(33)10-20(46)37-8-2-5-16(34)11-21(47)38-9-3-6-17(35)12-22(48)40-25-26(49)27(53-30(36)51)19(14-44)52-29(25)43-31-41-23-18(45)13-39-28(50)24(23)42-31/h15-19,23-27,29,44-45,49H,1-14,32-35H2,(H2,36,51)(H,37,46)(H,38,47)(H,39,50)(H,40,48)(H2,41,42,43)/t15-,16-,17-,18+,19+,23+,24-,25+,26-,27-,29+/m0/s1 |
| InChI Key | WUJTXMVGXDQPNN-OTQKCRDJSA-N |
Properties
| Appearance | White Hygroscopic Powder |
| Antibiotic Activity Spectrum | fungi; viruses |
| Melting Point | >210°C |
Reference Reading
1. 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+.
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. A-53930A and B, novel N-type Ca2+ channel blockers
M Hisamoto, Y Inaoka, Y Sakaida, T Kagazaki, R Enokida, T Okazaki, H Haruyama, T Kinoshita, K Matsuda J Antibiot (Tokyo). 1998 Jul;51(7):607-17. doi: 10.7164/antibiotics.51.607.
A-53930A, B and C, which inhibit N-type Ca2+ channels, were isolated from the culture broth of Streptomyces vinaceusdrappus SANK 62394. A-53930A and B were new compounds which contained a carbamoyl group on the 6-hydroxyl group of the D-gulosamine part of streptothricin. A-53930C was identical to streptothricin B. A-53930A, B and C inhibited [125I]omega-conotoxin MVIIA binding to N-type Ca2+ channels (IC50= 0.17, 0.091 and 0.071 microM), but did not inhibit [3H]PN200-110 binding to L-type Ca2+ channels (IC50 > 50 microM). These compounds also inhibited [3H]norepinephrine release from chick cerebral cortex synaptosomes (IC50=91.0, 20.6 and 39.5 microM), indicating these compounds selectively block N-type Ca2+ channels which are important for neurotransmitter release. It was also revealed that although A-53930C had antimicrobial activity against gram-negative and -positive bacteria and fungi, A-53930A and B showed weak activity only against gram-negative bacteria.
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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 ╳
