FR-33289
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| Category | Antibiotics |
| Catalog number | BBF-03550 |
| CAS | 73240-15-0 |
| Molecular Weight | 213.13 |
| Molecular Formula | C5H12NO6P |
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Description
FR-33289 is produced by the strain of Streptomyces rubellomurinus subsp. indigoferus 24. FR-33289 has anti-gram-positive and anti-gram-negative activities.
Specification
| Synonyms | Antibiotic FR 33289; (R)-(3-(Acetylhydroxyamino)-2-hydroxypropyl)phosphonic acid |
| IUPAC Name | [(2R)-3-[acetyl(hydroxy)amino]-2-hydroxypropyl]phosphonic acid |
| Canonical SMILES | CC(=O)N(CC(CP(=O)(O)O)O)O |
| InChI | InChI=1S/C5H12NO6P/c1-4(7)6(9)2-5(8)3-13(10,11)12/h5,8-9H,2-3H2,1H3,(H2,10,11,12)/t5-/m1/s1 |
| InChI Key | SMXUDUOWTDBXDT-RXMQYKEDSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 531.2±60.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Structural analysis of a phosphonate hydroxylase with an access tunnel at the back of the active site
Changqing Li, Muhammad Junaid, Eman Abdullah Almuqri, Shiguang Hao, Houjin Zhang Acta Crystallogr F Struct Biol Commun. 2016 May;72(Pt 5):362-8. doi: 10.1107/S2053230X16004933. Epub 2016 Apr 22.
FrbJ is a member of the Fe(2+)/α-ketoglutarate-dependent dioxygenase family which hydroxylates the natural product FR-900098 of Streptomyces rubellomurinus, yielding the phosphonate antibiotic FR-33289. Here, the crystal structure of FrbJ, which shows structural homology to taurine dioxygenase (TauD), a key member of the same family, is reported. Unlike other members of the family, FrbJ has an unusual lid structure which consists of two β-strands with a long loop between them. To investigate the role of this lid motif, a molecular-dynamics simulation was performed with the FrbJ structure. The molecular-dynamics simulation analysis implies that the lid-loop region is highly flexible, which is consistent with the fact that FrbJ has a relatively broad spectrum of substrates with different lengths. Interestingly, an access tunnel is found at the back of the active site which connects the putative binding site of α-ketoglutarate to the solvent outside.
2. Characterization and application of the Fe(II) and α-ketoglutarate dependent hydroxylase FrbJ
Matthew A DeSieno, Wilfred A van der Donk, Huimin Zhao Chem Commun (Camb). 2011 Sep 28;47(36):10025-7. doi: 10.1039/c1cc13597j. Epub 2011 Aug 10.
The Fe(II) and α-ketoglutarate-dependent hydroxylase FrbJ was previously demonstrated to utilize FR-900098 synthesizing a second phosphonate FR-33289. Here we assessed its ability to hydroxylate other possible substrates, generating a library of potential antimalarial compounds. Through a series of bioassays and in vitro experiments, we identified two new antimalarials.
3. Deciphering the late biosynthetic steps of antimalarial compound FR-900098
Tyler W Johannes, Matthew A DeSieno, Benjamin M Griffin, Paul M Thomas, Neil L Kelleher, William W Metcalf, Huimin Zhao Chem Biol. 2010 Jan 29;17(1):57-64. doi: 10.1016/j.chembiol.2009.12.009.
FR-900098 is a potent chemotherapeutic agent for the treatment of malaria. Here we report the heterologous production of this compound in Escherichia coli by reconstructing the entire biosynthetic pathway using a three-plasmid system. Based on this system, whole-cell feeding assays in combination with in vitro enzymatic activity assays reveal an unusual functional role of nucleotide conjugation and lead to the complete elucidation of the previously unassigned late biosynthetic steps. These studies also suggest a biosynthetic route to a second phosphonate antibiotic, FR-33289. A thorough understanding of the FR-900098 biosynthetic pathway now opens possibilities for metabolic engineering in E. coli to increase production of the antimalarial antibiotic and combinatorial biosynthesis to generate novel derivatives of FR-900098.
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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 ╳
