Furanomycin
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| Category | Antibiotics |
| Catalog number | BBF-01859 |
| CAS | 18455-25-9 |
| Molecular Weight | 157.17 |
| Molecular Formula | C7H11NO3 |
| Purity | 95% |
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Description
It can resist gram-positive and negative bacteria and inhibit the bacteriophage of Escherichia coli. It is also a L-isoleucine competitive antagonist.
Specification
| Synonyms | L-(+)-furanomycin; NSC 116328; (5S,2R,αS)-α-Amino-2,5-dihydro-5-methyl-2-furanacetic acid; L-xylo-Hept-4-enonic acid, 2-amino-3,6-anhydro-2,4,5,7-tetradeoxy- |
| IUPAC Name | (2S)-2-amino-2-[(2R,5S)-5-methyl-2,5-dihydrofuran-2-yl]acetic acid |
| Canonical SMILES | CC1C=CC(O1)C(C(=O)O)N |
| InChI | InChI=1S/C7H11NO3/c1-4-2-3-5(11-4)6(8)7(9)10/h2-6H,8H2,1H3,(H,9,10)/t4-,5+,6-/m0/s1 |
| InChI Key | PNOKUGWGMLEAPE-JKUQZMGJSA-N |
Properties
| Appearance | Achromatic Flake Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 305.6°C at 760 mmHg |
| Melting Point | 220-223°C |
| Density | 1.238 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddition strategy promoted by methylaluminoxane
Alberto Avenoza, Jesús H Busto, Noelia Canal, Francisco Corzana, Jesús M Peregrina, Marta Pérez-Fernández, Fernando Rodríguez J Org Chem. 2010 Feb 5;75(3):545-52. doi: 10.1021/jo9025258.
The synthesis and conformational analysis of a new type of conformationally restricted alpha-amino acid analogue of the amino acid antibiotic furanomycin is presented. The restriction involves the cis-fused cyclobutane and tetrahydrofuran units, generating the unusual 2-oxabicyclo[3.2.0]heptane core, which is found in a great number of biologically active natural products. The synthetic strategy is based on a formal [2 + 2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes and 2,3-dihydrofuran as a donor alkene, promoted by bulky aluminum-derived Lewis acids, particularly by methylaluminoxane (MAO). Additionally, following the same strategy, the synthesis of furanomycin analogues incorporating the 2-oxabicyclo[4.2.0]octane is reported.
2. Stereoselective Pd-catalyzed etherification and asymmetric synthesis of furanomycin and its analogues from a chiral aziridine
Jae-Hoon Jung, Doo-Ha Yoon, Kyuwoong Lee, Hyeonah Shin, Won Koo Lee, Cheol-Min Yook, Hyun-Joon Ha Org Biomol Chem. 2015 Aug 14;13(30):8187-95. doi: 10.1039/c5ob00375j.
A chiral aziridine was utilized for the synthesis of the anti-bacterial natural amino acid L-(+)-furanomycin, and its analogues including 5'-epi-furanomycin and norfuranomycin. Key steps of this synthesis are the stereoselective Pd-catalyzed etherification for diallyl ethers and ring closing metathesis.
3. Pseudomonas fluorescens SBW25 produces furanomycin, a non-proteinogenic amino acid with selective antimicrobial properties
Kristin Trippe, Kerry McPhail, Donald Armstrong, Mark Azevedo, Gary Banowetz BMC Microbiol. 2013 May 20;13:111. doi: 10.1186/1471-2180-13-111.
Background: Pseudomonas fluorescens SBW25 has been extensively studied because of its plant growth promoting properties and potential as a biocontrol agent. The genome of SBW25 has been sequenced, and among sequenced strains of pseudomonads, SBW25 appears to be most closely related to P. fluorescens WH6. In the authors' laboratories, WH6 was previously shown to produce and secrete 4-formylaminooxyvinylglycine (FVG), a non-proteinogenic amino acid with selective herbicidal and antimicrobial activity. Although SBW25 does not have the genetic capacity to produce FVG, we were interested in determining whether this pseudomonad might produce some other type of non-proteinogenic amino acid. Results: P. fluorescens SBW25 was found to produce and secrete a ninhydrin-reactive compound with selective antimicrobial properties. This compound was purified from SBW25 culture filtrate and identified as the non-proteinogenic amino acid L-furanomycin [2S,2'R,5'S)-2-amino-2-(5'methyl-2',5'-dihydrofuran-2'-yl)acetic acid]. Conclusions: The identification of furanomycin as a secondary metabolite of SBW25 is the first report of the production of furanomycin by a pseudomonad. This compound was known previously only as a natural product produced by a strain of Streptomyces. This report adds furanomycin to the small list of non-proteinogenic amino acids that have been identified as secondary products of pseudomonads. This study also extends the list of bacteria that are inhibited by furanomycin to include several plant pathogenic bacteria.
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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 ╳
