Fosfazinomycin B
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| Category | Antibiotics |
| Catalog number | BBF-01438 |
| CAS | 87423-11-8 |
| Molecular Weight | 354.30 |
| Molecular Formula | C10H23N6O6P |
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Description
Fosfazinomycin B is produced by the strain of Streptomyces lavendofoliae. It has the activity of resisting plant pathogenic fungi such as Xanthomonas oryzae.
Specification
| Synonyms | L-Arginine 2-[hydroxy(1-hydroxy-2-methoxy-2-oxoethyl)phosphinyl]-2-methyl hydrazide |
| IUPAC Name | N-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-(1-hydroxy-2-methoxy-2-oxoethyl)-N-methylphosphonamidic acid |
| Canonical SMILES | CN(NC(=O)C(CCCN=C(N)N)N)P(=O)(C(C(=O)OC)O)O |
| InChI | InChI=1S/C10H23N6O6P/c1-16(23(20,21)9(19)8(18)22-2)15-7(17)6(11)4-3-5-14-10(12)13/h6,9,19H,3-5,11H2,1-2H3,(H,15,17)(H,20,21)(H4,12,13,14)/t6-,9?/m0/s1 |
| InChI Key | DDNXSURUODEJRT-AADKRJSRSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Solubility | Soluble in Water |
Reference Reading
1. Biosynthesis of fosfazinomycin is a convergent process
Zedu Huang, Kwo-Kwang A Wang, Jaeheon Lee, Wilfred A van der Donk Chem Sci. 2015 Feb 1;6(2):1282-1287. doi: 10.1039/C4SC03095H.
Fosfazinomycin A is a phosphonate natural product in which the C-terminal carboxylate of a Val-Arg dipeptide is connected to methyl 2-hydroxy-2-phosphono-acetate (Me-HPnA) via a unique hydrazide linkage. We report here that Me-HPnA is generated from phosphonoacetaldehyde (PnAA) in three biosynthetic steps through the combined action of an O-methyltransferase (FzmB) and an α-ketoglutarate (α-KG) dependent non-heme iron dioxygenase (FzmG). Unexpectedly, the latter enzyme is involved in two different steps, oxidation of the PnAA to phosphonoacetic acid as well as hydroxylation of methyl 2-phosphonoacetate. The N-methyltransferase (FzmH) was able to methylate Arg-NHNH2 (3) to give Arg-NHNHMe (4), constituting the second segment of the fosfazinomycin molecule. Methylation of other putative intermediates such as desmethyl fosfazinomycin B was not observed. Collectively, our current data support a convergent biosynthetic pathway to fosfazinomycin.
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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 ╳
