Phoslactomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02406 |
| CAS | 122856-25-1 |
| Molecular Weight | 599.65 |
| Molecular Formula | C29H46NO10P |
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Description
It is produced by the strain of Str. nigrescens. The main component E has weak effect against gram-positive bacteria, but has strong effect against fungi. Its antimicrobial activity is similar to Phoslactomycin E.
Specification
| Synonyms | Propanoic acid, 2-methyl-, (1S,3R)-3-[(1Z,3Z,5R,7R,8R,9E)-8-(2-aminoethyl)-10-[(2S,3S)-3-ethyl-3,6-dihydro-6-oxo-2H-pyran-2-yl]-5,8-dihydroxy-7-(phosphonooxy)-1,3,9-decatrien-1-yl]cyclohexyl ester; Propanoic acid, 2-methyl-, 3-[8-(2-aminoethyl)-10-(3-ethyl-3,6-dihydro-6-oxo-2H-pyran-2-yl)-5,8-dihydroxy-7-(phosphonooxy)-1,3,9-decatrienyl]cyclohexyl ester, [2S-[2a[1Z(1R*,3S*),3Z,5S*,7S*,8S*,9E],3a]]-; (+)-Phoslactomycin A |
| IUPAC Name | [(1S,3R)-3-[(1Z,3Z,5R,7R,8R,9E)-8-(2-aminoethyl)-10-[(2S,3S)-3-ethyl-6-oxo-2,3-dihydropyran-2-yl]-5,8-dihydroxy-7-phosphonooxydeca-1,3,9-trienyl]cyclohexyl] 2-methylpropanoate |
| Canonical SMILES | CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCC(C2)OC(=O)C(C)C)O)OP(=O)(O)O)O |
| InChI | InChI=1S/C29H46NO10P/c1-4-22-12-13-27(32)39-25(22)14-15-29(34,16-17-30)26(40-41(35,36)37)19-23(31)10-6-5-8-21-9-7-11-24(18-21)38-28(33)20(2)3/h5-6,8,10,12-15,20-26,31,34H,4,7,9,11,16-19,30H2,1-3H3,(H2,35,36,37)/b8-5-,10-6-,15-14+/t21-,22+,23+,24+,25+,26-,29+/m1/s1 |
| InChI Key | LOAKADZNOAGFPM-DCUAGDHESA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Boiling Point | 792.0°C at 760 mmHg |
| Melting Point | 165-168°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Good timing in total synthesis: the case of phoslactomycin A
Björn Gebhardt, Christian M König, Cornelia Schleth, Mario Dauber, Ulrich Koert Chemistry. 2010 May 25;16(20):5934-41. doi: 10.1002/chem.201000104.
The importance for the right order of functional group introduction and manipulation (good timing) was demonstrated in the course of a total synthesis of phoslactomycin A. The synthetic strategy comprised a Cu(I)-thiophene carboxylate (CuTC, Liebeskind's reagent)-mediated coupling to introduce the Z,Z-diene at the final stage of the synthesis in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-aldol reaction and an advanced protective group strategy. The C14-C21 fragment was accessible via an asymmetric 1,2-addition to cyclohexenone and a subsequent diastereoselective ketone reduction. One crucial task was the dihydroxylation of the C8-C9 alkene, the introduction of the C6-C7 double bond and the generation of the C25-nitrogen functionality. A second example consisted of the best sequence for the generation of the functional groups in the core part (first phosphorylation, second iodo-olefination, third azide/carbamate conversion). The synthetic solutions from this approach are compared with the already existing contributions in the phoslactomycin area.
2. 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.
3. Identification of phoslactomycin biosynthetic gene clusters from Streptomyces platensis SAM-0654 and characterization of PnR1 and PnR2 as positive transcriptional regulators
Yun-Liang Chen, Juan Zhao, Wei Liu, Ju-Fang Gao, Li-Ming Tao, Hai-Xue Pan, Gong-Li Tang Gene. 2012 Nov 10;509(2):195-200. doi: 10.1016/j.gene.2012.08.030. Epub 2012 Aug 25.
Phoslactomycins (PLMs) are inhibitors of protein serine/threonine phosphatase 2A showing diverse and important antifungal, antibacterial and antitumor activity. PLMs are polyketide natural products and produced by several Streptomyces species. The PLMs biosynthetic gene clusters were identified from Streptomyces platensis SAM-0654 and localized in two separate genomic regions, consisting of 27 open reading frames that encode polyketide synthases (PKSs), enzymes for cyclohexanecarboxyl-CoA (CHC-CoA) and ethylmalonyl-CoA (Em-CoA) synthesis, enzymes for post-PKS modifications, proposed regulators, and putative resistance transporters. Bioinformatic analysis and inactivation experiment of regulatory genes suggest that PnR1 and PnR2 are two positive regulators of PLMs biosynthesis. Gene transcription analysis by reverse transcriptase PCR (RT-PCR) of the PLMs gene cluster demonstrated that PnR1 and PnR2 activate the transcription of the structural biosynthetic genes while PnR2 specially governs the transcription of pnR1 in a higher level.
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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 ╳
