Lavendomycin
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| Category | Antibiotics |
| Catalog number | BBF-02244 |
| CAS | 82987-09-5 |
| Molecular Weight | 666.78 |
| Molecular Formula | C29H50N10O8 |
| Purity | ≥95% |
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Description
It is produced by the strain of Str. lavendulae subsp. brasillicus. It has strong activity against Staphylococcus aureus, Staphylococcus epidermococcus and Streptococcus faecalis with ED50 (mg/kg) of 2.33, 1.68 and 13.2, respectively (In vivo test in mice, abdominal infection, subcutaneous administration). It has no anti-gram-negative bacteria and fungi activity.
Specification
| Synonyms | Antibiotic FR 900201; ((Z)-2-((S)-1-((S)-1-((2S,3R)-3-amino-2-((2S,3R)-2-amino-5-guanidino-3-methylpentanamido)butanoyl)piperidine-2-carbonyl)pyrrolidine-2-carboxamido)but-2-enoyl)-L-serine |
| IUPAC Name | (2S)-2-[[(Z)-2-[[(2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-[[(2S,3R)-2-amino-5-(diaminomethylideneamino)-3-methylpentanoyl]amino]butanoyl]piperidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]but-2-enoyl]amino]-3-hydroxypropanoic acid |
| Canonical SMILES | CC=C(C(=O)NC(CO)C(=O)O)NC(=O)C1CCCN1C(=O)C2CCCCN2C(=O)C(C(C)N)NC(=O)C(C(C)CCN=C(N)N)N |
| InChI | InChI=1S/C29H50N10O8/c1-4-17(23(41)36-18(14-40)28(46)47)35-24(42)19-9-7-13-38(19)26(44)20-8-5-6-12-39(20)27(45)22(16(3)30)37-25(43)21(31)15(2)10-11-34-29(32)33/h4,15-16,18-22,40H,5-14,30-31H2,1-3H3,(H,35,42)(H,36,41)(H,37,43)(H,46,47)(H4,32,33,34)/b17-4-/t15-,16-,18+,19+,20+,21+,22+/m1/s1 |
| InChI Key | ZLIFOKMGWXMKQW-BDKIHTTOSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >205°C (dec.) |
| Density | 1.50 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. 3-Methylarginine from Pseudomonas syringae pv. syringae 22d/93 suppresses the bacterial blight caused by its close relative Pseudomonas syringae pv. glycinea
Sascha D Braun, Beate Völksch, Jörg Nüske, Dieter Spiteller Chembiochem. 2008 Aug 11;9(12):1913-20. doi: 10.1002/cbic.200800080.
The epiphyte Pseudomonas syringae pv. syringae 22d/93 (Pss22d) produces a toxin that strongly inhibits the growth of its relative, the plant pathogen P. syringae pv. glycinea. The inhibition can be overcome by supplementing the growth medium with the essential amino acid, L-arginine; this suggests that the toxin acts as an inhibitor of the arginine biosynthesis. The highly polar toxin was purified by bioassay-guided fractionation using ion-exchange chromatography and subsequent RP-HPLC fractionation. The structure of the natural product was identified by HR-ESI-MS, HR-ESI-MS/MS, and NMR spectroscopy experiments as 3-methylarginine. This amino acid has previously only been known in nature as a constituent of the peptide lavendomycin from Streptomyces lavendulae. Results of experiments in which labeled methionine was fed to Pss22d indicated that the key step in the biosynthesis of 3-methylarginine is the introduction of the methyl group by a S-adenosylmethionine (SAM)-dependent methyltransferase. Transposon mutagenesis of Pss22d allowed the responsible SAM-dependent methyltransferase of the 3-methylarginine biosynthesis to be identified.
2. Lavendomycin, a new antibiotic. I. Taxonomy, isolation and characterization
T Komori, M Ezaki, E Kino, M Kohsaka, H Aoki, H Imanaka J Antibiot (Tokyo). 1985 Jun;38(6):691-8. doi: 10.7164/antibiotics.38.691.
Lavendomycin, a new basic peptide antibiotic containing novel amino acids, has been isolated from the culture broth of a streptomyces designated as Streptomyces lavendulae subsp. brasilicus. The antibiotic obtained as colorless crystals (C29H50N10O8, MW 666) is active against Gram-positive bacteria in vitro and in vivo, however, inactive against Gram-negative bacteria and fungi. An acute toxicity of the antibiotic in mice was LD50 greater than 2 g/kg by subcutaneous injection.
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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 ╳
