Phoslactomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02407 |
| CAS | 122856-26-2 |
| Molecular Weight | 513.56 |
| Molecular Formula | C25H40NO8P |
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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 | (+)-Phoslactomycin B; 2H-Pyran-2-one, 6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrien-1-yl]-5-ethyl-5,6-dihydro-, (5S,6S)- |
| IUPAC Name | [(1E,3R,4R,6R,7Z,9Z)-3-(2-aminoethyl)-10-cyclohexyl-1-[(2S,3S)-3-ethyl-6-oxo-2,3-dihydropyran-2-yl]-3,6-dihydroxydeca-1,7,9-trien-4-yl] dihydrogen phosphate |
| Canonical SMILES | CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCCC2)O)OP(=O)(O)O)O |
| InChI | InChI=1S/C25H40NO8P/c1-2-20-12-13-24(28)33-22(20)14-15-25(29,16-17-26)23(34-35(30,31)32)18-21(27)11-7-6-10-19-8-4-3-5-9-19/h6-7,10-15,19-23,27,29H,2-5,8-9,16-18,26H2,1H3,(H2,30,31,32)/b10-6-,11-7-,15-14+/t20-,21-,22-,23+,25-/m0/s1 |
| InChI Key | GAIPQMSJLNWRGC-MZAVDHTQSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Boiling Point | 753.1°C at 760 mmHg |
| Melting Point | 161-163°C |
| Density | 1.309 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Understanding Substrate Selectivity of Phoslactomycin Polyketide Synthase by Using Reconstituted in Vitro Systems
Kyra Geyer, Srividhya Sundaram, Peter Sušnik, Ulrich Koert, Tobias J Erb Chembiochem. 2020 Jul 16;21(14):2080-2085. doi: 10.1002/cbic.202000112. Epub 2020 Mar 30.
Polyketide synthases (PKSs) use simple extender units to synthesize complex natural products. A fundamental question is how different extender units are site-specifically incorporated into the growing polyketide. Here we established phoslactomycin (Pn) PKS, which incorporates malonyl- and ethylmalonyl-CoA, as an in vitro model to study substrate specificity. We combined up to six Pn PKS modules with different termination sites for the controlled release of tetra-, penta- and hexaketides, and challenged these systems with up to seven different extender units in competitive assays to test for the specificity of Pn modules. While malonyl-CoA modules of Pn PKS exclusively accept their natural substrate, the ethylmalonyl-CoA module PnC tolerates different α-substituted derivatives, but discriminates against malonyl-CoA. We show that the ratio of extender transacylation to hydrolysis controls incorporation in PnC, thus explaining site-specific selectivity and promiscuity in the natural context of Pn PKS.
2. Deamino-hydroxy-phoslactomycin B, a biosynthetic precursor of phoslactomycin, induces myeloid differentiation in HL-60 cells
Siro Simizu, Takayuki Teruya, Toshihiko Nogawa, Harumi Aono, Masashi Ueki, Masakazu Uramoto, Yuichi Kobayashi, Hiroyuki Osada Biochem Biophys Res Commun. 2009 Jun 12;383(4):406-10. doi: 10.1016/j.bbrc.2009.04.014. Epub 2009 Apr 11.
During the screening for novel differentiation inducers, we found that a culture broth of Streptomyces sp. HK-803 induced myeloid differentiation of HL-60 cells. The active substance was identified as deamino-hydroxy-phoslactomycin B (HPLM) by mass spectrometry, and synthesized HPLM also induced the differentiation of HL-60 cells. HPLM showed greater inhibition of protein phosphatase 2A (PP2A) activity than phoslactomycin B (PLMB); however, PLMB and okadaic acid did not induce differentiation. Moreover, treatment with ATRA and 1alpha, 25(OH)2D3 induced retinoic acid receptor-beta and 1alpha, 25(OH)2D3 24-hydroxylase, respectively, whereas HPLM did not, suggesting that HPLM is a novel differentiation inducer.
3. Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B
Shaheen M Sarkar, Everlyne N Wanzala, Setsuya Shibahara, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama Chem Commun (Camb). 2009 Oct 21;(39):5907-9. doi: 10.1039/b912267b. Epub 2009 Aug 10.
A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.
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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 ╳
