Leucinostatin H

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Category Antibiotics
Catalog number BBF-02254
CAS 109539-58-4
Molecular Weight 1134.49
Molecular Formula C57H103N11O12

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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.

Specification

Synonyms Paecilotoxin H; N-(1-(aminooxy)-26-(1-hydroxy-2-methylpropyl)-17,20-diisobutyl-4,11,11,14,14,23,23,31-octamethyl-6,10,13,16,19,22,25,28-octaoxo-5,9,12,15,18,21,24,27-octaazadotriacontan-29-yl)-4-methyl-1-((R,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxamide; Leucinostatin A, 2-L-leucine, N9-oxide
IUPAC Name N-[1-[[1-[[1-[[1-[[1-[[1-[[1-[[3-(5-aminooxypentan-2-ylamino)-3-oxopropyl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-hydroxy-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methyl-1-[(E,4R)-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)CCCON)C
InChI InChI=1S/C57H103N11O12/c1-19-36(10)22-23-44(70)68-31-37(11)30-42(68)50(75)62-39(27-32(2)3)48(73)64-45(46(71)35(8)9)51(76)66-56(15,16)53(78)63-40(28-33(4)5)47(72)61-41(29-34(6)7)49(74)65-57(17,18)54(79)67-55(13,14)52(77)59-25-24-43(69)60-38(12)21-20-26-80-58/h22-23,32-42,45-46,71H,19-21,24-31,58H2,1-18H3,(H,59,77)(H,60,69)(H,61,72)(H,62,75)(H,63,78)(H,64,73)(H,65,74)(H,66,76)(H,67,79)/b23-22+/t36-,37?,38?,39?,40?,41?,42?,45?,46?/m1/s1
InChI Key BAYBYMBPRYTYMY-JNSBAATBSA-N

Properties

Appearance White Partial Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Fungi
Boiling Point 1357.4°C at 760 mmHg
Melting Point 166-168°C
Density 1.116 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.

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