FR-900098
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| Category | Antibiotics |
| Catalog number | BBF-03695 |
| CAS | 66508-32-5 |
| Molecular Weight | 197.13 |
| Molecular Formula | C5H12NO5P |
| Purity | >98% |
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Description
FR-900098 is produced by the strain of Streptomyces rubellomurinus subsp. indigoferus 24. FR-900098 has anti-gram-positive and anti-gram-negative activities.
Specification
| Synonyms | Antibiotic FR-900098; FR 900098; BRN 2096083; 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid |
| Storage | Store at -20°C |
| IUPAC Name | 3-[acetyl(hydroxy)amino]propylphosphonic acid |
| Canonical SMILES | CC(=O)N(CCCP(=O)(O)O)O |
| InChI | InChI=1S/C5H12NO5P/c1-5(7)6(8)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11) |
| InChI Key | PKMNDDZSIHLLLI-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 430.9°C at 760 mmHg |
| Density | 1.497 g/cm3 |
Reference Reading
1. FR-900098, an antimalarial development candidate that inhibits the non-mevalonate isoprenoid biosynthesis pathway, shows no evidence of acute toxicity and genotoxicity
Jochen Wiesner, Christina Ziemann, Martin Hintz, Armin Reichenberg, Regina Ortmann, Martin Schlitzer, Rainer Fuhst, Nina Timmesfeld, Andreas Vilcinskas, Hassan Jomaa Virulence. 2016 Aug 17;7(6):718-28. doi: 10.1080/21505594.2016.1195537. Epub 2016 Jun 3.
FR-900098 is an inhibitor of 1-deoxy-d-xylulose-5-phosphate (DXP) reductoisomerase, the second enzyme in the non-mevalonate isoprenoid biosynthesis pathway. In previous studies, FR-900098 was shown to possess potent antimalarial activity in vitro and in a murine malaria model. In order to provide a basis for further preclinical and clinical development, we studied the acute toxicity and genotoxicity of FR-900098. We observed no acute toxicity in rats, i.e. there were no clinical signs of toxicity and no substance-related deaths after the administration of a single dose of 3000 mg/kg body weight orally or 400 mg/kg body weight intravenously. No mutagenic potential was detected in the Salmonella typhimurium reverse mutation assay (Ames test) or an in vitro mammalian cell gene mutation test using mouse lymphoma L5178Y/TK(+/-) cells (clone 3.7.2C), both with and without metabolic activation. In addition, FR-900098 demonstrated no clastogenic or aneugenic capability or significant adverse effects on blood formation in an in vivo micronucleus test with bone marrow erythrocytes from NMRI mice. We conclude that FR-900098 lacks acute toxicity and genotoxicity, supporting its further development as an antimalarial drug.
2. Potentiation of the Fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
Matthew D Stephens, Nisakorn Yodsanit, Christian Melander Medchemcomm. 2016;7(10):1952-1956. doi: 10.1039/C6MD00365F. Epub 2016 Jul 27.
A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.
3. Characterization of the flavin monooxygenase involved in biosynthesis of the antimalarial FR-900098
Kim Nguyen, Matthew A DeSieno, Brian Bae, Tyler W Johannes, Ryan E Cobb, Huimin Zhao, Satish K Nair Org Biomol Chem. 2019 Feb 6;17(6):1506-1518. doi: 10.1039/c8ob02840k.
The latter steps in this biosynthetic pathway for the antimalarial phosphonic acid FR-900098 include the installation of a hydroxamate onto 3-aminopropylphosphonate, which is catalyzed by the consecutive actions of an acetyltransferase and an amine hydroxylase. Here, we present the 1.6 Å resolution co-crystal structure and accompanying biochemical characterization of FrbG, which catalyzes the hydroxylation of aminopropylphosphonate. We show that FrbG is a flavin-dependent N-hydroxylating monooxygenase (NMO), which shares a similar overall structure with flavin-containing monooxygenases (FMOs). Notably, we also show that the cytidine-5'-monophosphate moiety of the substrate is a critical determinant of specificity, distinguishing FrbG from other FMOs in that the nucleotide cofactor-binding domain also serves in conferring substrate recognition. In the FrbG-FAD+-NADPH co-crystal structure, the C4 of the NADPH nicotinamide is situated near the N5 of the FAD isoalloxazine, and is oriented with a distance and stereochemistry to facilitate hydride transfer.
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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 ╳
