Micacocidin C

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Category Antibiotics
Catalog number BBF-01935
CAS
Molecular Weight 618.63
Molecular Formula C27H36FeN3O4S3

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Description

Micacocidin C is an antibiotic produced by Pseudomonas sp.No.57. It exhibited an excellent activity against Mycoplasma species.

Specification

IUPAC Name iron(3+);(4S)-4-methyl-2-[(1R)-2-methyl-1-[(2R,4R)-3-methyl-2-[(4R)-2-(2-oxido-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl]-1-oxidopropan-2-yl]-5H-1,3-thiazole-4-carboxylate
Canonical SMILES CCCCCC1=C(C(=CC=C1)[O-])C2=NC(CS2)C3N(C(CS3)C(C(C)(C)C4=NC(CS4)(C)C(=O)[O-])[O-])C.[Fe+3]
InChI InChI=1S/C27H38N3O4S3.Fe/c1-6-7-8-10-16-11-9-12-19(31)20(16)22-28-17(13-35-22)23-30(5)18(14-36-23)21(32)26(2,3)24-29-27(4,15-37-24)25(33)34;/h9,11-12,17-18,21,23,31H,6-8,10,13-15H2,1-5H3,(H,33,34);/q-1;+3/p-2/t17-,18+,21+,23-,27-;/m1./s1
InChI Key ANYHWHQDULLETA-LRLOAOIRSA-L

Properties

Appearance Reddish Brown Powder
Antibiotic Activity Spectrum mycoplasma
Boiling Point 740.3±70.0°C at 760 mmHg
Density 1.4±0.1 g/cm3

Reference Reading

1. Micacocidin A, B and C, novel antimycoplasma agents from Pseudomonas sp. II. Structure elucidation
S Kobayashi, H Nakai, Y Ikenishi, W Y Sun, M Ozaki, Y Hayase, R Takeda J Antibiot (Tokyo). 1998 Mar;51(3):328-32. doi: 10.7164/antibiotics.51.328.
Metal-containing novel heterocyclic antibiotics, micacocidin A (1), B (2), and C (3) have been isolated from the culture filtrate of Pseudomonas sp. No. 57-250. The structure and absolute configuration of micacocidin A, an octahedral Zn2+ complex, was determined by X-ray crystallographic analysis. And then, the structures of the two congeners, micacocidin B (Cu2+ complex) and C (Fe3+ complex) were investigated by employing one dimensional and two dimensional homonuclear and heteronuclear NMR spectroscopies and mass spectrometry.
2. Micacocidin A, B and C, novel antimycoplasma agents from Pseudomonas sp. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
S Kobayashi, S Hidaka, Y Kawamura, M Ozaki, Y Hayase J Antibiot (Tokyo). 1998 Mar;51(3):323-7. doi: 10.7164/antibiotics.51.323.
A Gram-negative bacterium was found to produce a new zinc-containing antibiotics, micacocidin A and related compounds containing Cu or Fe, micacocidin B and C, respectively. These antibiotics were isolated by column chromatography on silica gel, and then separated by preparative TLC and HPLC. These new antibiotics exhibited an excellent activity against Mycoplasma species. The producing bacterium was characterized and ascribed to the genus Pseudomonas.

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