Phoslactomycin E
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| Category | Antibiotics |
| Catalog number | BBF-02410 |
| CAS | 122856-29-5 |
| Molecular Weight | 639.71 |
| Molecular Formula | C32H50NO10P |
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Description
It is produced by the strain of Str. nigrescens. It is the main component, which has weak effect against gram-positive bacteria, but has strong effect against fungi.
Specification
| Synonyms | Cyclohexanecarboxylic Acid, 3-(8-(2-Aminoethyl)-10-(3-Ethyl-3,6-Dihydro-6-Oxo-2H-Pyran-2-Yl)-5,8-Dihydroxy-7-(Phophonooxy)-1,3,9-Decatrienyl)Cyclohexyl Ester |
| IUPAC Name | [3-[(1E,3E,9E)-8-(2-aminoethyl)-10-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-5,8-dihydroxy-7-phosphonooxydeca-1,3,9-trienyl]cyclohexyl] cyclohexanecarboxylate |
| Canonical SMILES | CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCC(C2)OC(=O)C3CCCCC3)O)OP(=O)(O)O)O |
| InChI | InChI=1S/C32H50NO10P/c1-2-24-15-16-30(35)42-28(24)17-18-32(37,19-20-33)29(43-44(38,39)40)22-26(34)13-7-6-9-23-10-8-14-27(21-23)41-31(36)25-11-4-3-5-12-25/h6-7,9,13,15-18,23-29,34,37H,2-5,8,10-12,14,19-22,33H2,1H3,(H2,38,39,40)/b9-6+,13-7+,18-17+ |
| InChI Key | VPPYLHODJVARBC-XUQJEITOSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Boiling Point | 830.4°C at 760 mmHg |
| Melting Point | 168-171°C |
| Density | 1.27 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Application of a newly identified and characterized 18-o-acyltransferase in chemoenzymatic synthesis of selected natural and nonnatural bioactive derivatives of phoslactomycins
Mohini S Ghatge, Nadaraj Palaniappan, Ma'moun M Alhamadsheh, Jessica DiBari, Kevin A Reynolds Appl Environ Microbiol. 2009 Jun;75(11):3469-76. doi: 10.1128/AEM.02590-08. Epub 2009 Mar 20.
Phoslactomycins (PLMs) and related leustroducsins (LSNs) have been isolated from a variety of bacteria based on antifungal, anticancer, and other biological assays. Streptomyces sp. strain HK 803 produces five PLM analogs (PLM A and PLMs C to F) in which the C-18 hydroxyl substituent is esterified with a range of branched, short-alkyl-chain carboxylic acids. The proposed pathway intermediate, PLM G, in which the hydroxyl residue is not esterified has not been observed at any significant level in fermentation, and the only route to this potentially useful intermediate has been an enzymatic deacylation of other PLMs and LSNs. We report that deletion of plmS(3) from the PLM biosynthetic cluster gives rise to a mutant which accumulates the PLM G intermediate. The 921-bp plmS(3) open reading frame was cloned and expressed as an N-terminally polyhistidine-tagged protein in Escherichia coli and shown to be an 18-O acyltransferase, catalyzing conversion of PLM G to PLM A, PLM C, and PLM E using isobutyryl coenzyme A (CoA), 3-methylbutyryl-CoA, and cyclohexylcarbonyl-CoA, respectively. The efficiency of this process (k(cat) of 28 +/- 3 min(-1) and K(m) of 88 +/- 16 microM) represents a one-step chemoenzymatic alternative to a multistep synthetic process for selective chemical esterification of the C-18 hydroxy residue of PLM G. PlmS(3) was shown to catalyze esterification of PLM G with CoA and N-acetylcysteamine thioesters of various saturated, unsaturated, and aromatic carboxylic acids and thus also to provide an efficient chemoenzymatic route to new PLM analogs.
2. Phoslactomycins Revisited: Polyketide Tetrahydrofurans and Lactones from an Australian Wasp Nest-Derived Streptomyces sp. CMB-MW079
Angela A Salim, Kaumadi Samarasekera, Taizong Wu, Robert J Capon Org Lett. 2022 Oct 14;24(40):7328-7333. doi: 10.1021/acs.orglett.2c02791. Epub 2022 Oct 6.
Molecular network analysis of Streptomyces sp. CMB-MW079 detected rare phosphorylated natural products. Miniaturized cultivation profiling (MATRIX) established optimal conditions for the production, isolation, and identification of the polyketide δ-lactone phoslactomycin E (1) and new ester homologues, phoslactomycins J and K (2 and 3), as well as unprecedented heterocyclic analogues, the tetrahydrofuran cyclolactomycins A-D (4-7) and γ-lactone isocyclolactomycins A-C (8-10). We propose a biogenetic relationship linking these cometabolites with the known lactomycins A-C which were tentatively identified as minor cometabolites.
3. Identification of phoslactomycin E as a metabolite inducing hyphal morphological abnormalities in Aspergillus fumigatus IFO 5840
Naoko Mizuhara, Yoshinosuke Usuki, Masaki Ogita, Ken-Ichi Fujita, Manabu Kuroda, Matsumi Doe, Hideo Iio, Toshio Tanaka J Antibiot (Tokyo). 2007 Dec;60(12):762-5. doi: 10.1038/ja.2007.101.
In our survey for antifungal compounds, a fermentation broth of Streptomyces sp. HA81-2 was found to inhibit the in vitro growth of Aspergillus fumigatus IFO 5840 accompanied by hyphal morphological abnormalities. One of the isolated antibiotics was identified as phoslactomycin E based on LC-MS and NMR spectral data. In a preliminary assay using the membrane fractions of A. fumigatus, phoslactomycin E was found to inhibit the activity of 1,3-beta glucan synthase.
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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 ╳
