Leucinostatin D
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| Category | Antibiotics |
| Catalog number | BBF-02253 |
| CAS | 100334-47-2 |
| Molecular Weight | 1104.47 |
| Molecular Formula | C56H101N11O11 |
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Description
It is produced by the strain of Paecilomyces marquandii. It's a peptide antibiotic. It has anti-gram-positive bacterial and fungal effects. It has in vitro cytotoxic activity against HeLa 850, KB cells and sensitive leukemia cells P388 with ID50 of 1.00 ng/mL.
Specification
| Synonyms | Paecilotoxin D; (4R)-N-[1-[[2-hydroxy-3-methyl-1-[2-[[3-methyl-1-[[3-methyl-1-[2-[2-[2-(1-methylaminopropan-2-ylcarbamoyl)ethylcarbamoyl]propan-2-ylcarbamoyl]propan-2-ylcarbamoyl]butyl]carbamoyl]butyl]carbamoyl]propan-2-ylcarbamoyl]butyl]carbamoyl]-3-methyl-butyl]-4-methyl-1-[(E,4S)-4-methylhex-2-enoyl]pyrrolidine-2-carboxamide |
| IUPAC Name | (4R)-N-[1-[[3-hydroxy-4-methyl-1-[[2-methyl-1-[[4-methyl-1-[[4-methyl-1-[[2-methyl-1-[[2-methyl-1-[[3-[1-(methylamino)propan-2-ylamino]-3-oxopropyl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methyl-1-[(E,4S)-4-methylhex-2-enoyl]pyrrolidine-2-carboxamide |
| Canonical SMILES | CCC(C)C=CC(=O)N1CC(CC1C(=O)NC(CC(C)C)C(=O)NC(C(C(C)C)O)C(=O)NC(C)(C)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NCCC(=O)NC(C)CNC)C |
| InChI | InChI=1S/C56H101N11O11/c1-20-35(10)21-22-43(69)67-30-36(11)28-41(67)49(74)61-38(25-31(2)3)47(72)63-44(45(70)34(8)9)50(75)65-55(15,16)52(77)62-39(26-32(4)5)46(71)60-40(27-33(6)7)48(73)64-56(17,18)53(78)66-54(13,14)51(76)58-24-23-42(68)59-37(12)29-57-19/h21-22,31-41,44-45,57,70H,20,23-30H2,1-19H3,(H,58,76)(H,59,68)(H,60,71)(H,61,74)(H,62,77)(H,63,72)(H,64,73)(H,65,75)(H,66,78)/b22-21+/t35-,36+,37?,38?,39?,40?,41?,44?,45?/m0/s1 |
| InChI Key | RDUJTYZLXJPVKP-YDZNBPEVSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor); Fungi |
| Boiling Point | 1323.8°C at 760 mmHg |
| Melting Point | 184-185°C |
| Density | 1.106 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. Paecilotoxin production in clinical or terrestrial isolates of Paecilomyces lilacinus strains
Y Mikami, K Yazawa, K Fukushima, T Arai, S Udagawa, R A Samson Mycopathologia. 1989 Dec;108(3):195-9. doi: 10.1007/BF00436225.
The production of paecilotoxin from various isolates of Paecilomyces lilacinus was studied using three different media and high performance liquid chromatography (HPLC). Alkaline medium was found to be suitable for the production of the toxins. Among 20 strains tested, 19 including four clinical isolates were found to produce the toxins. Production patterns of paecilotoxins were very similar in each strain and the main toxins were A and B.
2. Liquid chromatography-tandem mass spectrometry characterization of five new leucinostatins produced by Paecilomyces lilacinus CG-189
Ana Flávia Canovas Martinez, Luiz Alberto Beraldo Moraes J Antibiot (Tokyo). 2015 Mar;68(3):178-84. doi: 10.1038/ja.2014.120. Epub 2014 Sep 3.
The fungus Paecilomyces lilacinus produces leucinostatins-peptaibiotics that exert a range of biological activities including antimalarial, antiviral, antitumor and phytotoxicity. In this paper, we developed an analytical method employing LC-MS/MS in the precursor ion and product ion scan modes to elucidate five new leucinostatins. Direct Infusion (DI-MS) helped to identify the most abundant leucinostatins: F, D B2, S, A and K. MS/MS analysis using a triple quadrupole operating at different scan modes is a versatile tool to study natural products, especially peptaibiotics. Although DI-MS full-scan analysis is rapid and sensitive, it cannot distinguish between peptide isomers. On the other hand, LC-MS/MS operated in the precursor ion and product ion modes is time consuming, but allows identifying the structure of isomers or isobar in crude extracts.
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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 ╳
