Phoslactomycin D
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| Category | Antibiotics |
| Catalog number | BBF-02409 |
| CAS | 122856-28-4 |
| Molecular Weight | 627.70 |
| Molecular Formula | C31H50NO10P |
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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 | Pentanoic acid, 4-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 |
| 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] 4-methylpentanoate |
| Canonical SMILES | CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCC(C2)OC(=O)CCC(C)C)O)OP(=O)(O)O)O |
| InChI | InChI=1S/C31H50NO10P/c1-4-24-13-15-30(35)41-27(24)16-17-31(36,18-19-32)28(42-43(37,38)39)21-25(33)10-6-5-8-23-9-7-11-26(20-23)40-29(34)14-12-22(2)3/h5-6,8,10,13,15-17,22-28,33,36H,4,7,9,11-12,14,18-21,32H2,1-3H3,(H2,37,38,39)/b8-5+,10-6+,17-16+ |
| InChI Key | AAYSLXZWMOLRDM-NAOUFDFXSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi |
| Boiling Point | 805.0°C at 760 mmHg |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Studies on new phosphate ester antifungal antibiotics phoslactomycins. II. Structure elucidation of phoslactomycins A to F
S Fushimi, K Furihata, H Seto J Antibiot (Tokyo). 1989 Jul;42(7):1026-36. doi: 10.7164/antibiotics.42.1026.
Phoslactomycins A to F are new antifungal antibiotics produced by Streptomyces nigrescens SC-273. On the basis of physico-chemical properties and NMR studies, their structures have been determined as shown in Fig. 6. They are characterized by possessing alpha, beta-unsaturated delta-lactone, phosphate ester, conjugated diene and cyclohexane ring moieties. The structural difference between them is ascribed to a substituent bound to the cyclohexane ring.
2. 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.
3. Studies on new phosphate ester antifungal antibiotics phoslactomycins. I. Taxonomy, fermentation, purification and biological activities
S Fushimi, S Nishikawa, A Shimazu, H Seto J Antibiot (Tokyo). 1989 Jul;42(7):1019-25. doi: 10.7164/antibiotics.42.1019.
New antibiotics phoslactomycins A, B, C, D, E and F, which contain alpha, beta-unsaturated delta-lactone, phosphate ester, conjugated diene and cyclohexane ring moieties, were isolated from the culture broth of a soil isolate actinomycete. Morphological, cultural and physiological studies revealed that the isolate is a strain of Streptomyces nigrescens. Phoslactomycins were obtained by butanol extraction, gel filtration and reverse phase chromatography. The antibiotics show strong activity against various fungi, particularly phytopathogenic fungi (Botrytis cinerea and Alternaria kikuchiana).
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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 ╳
