Bialaphos

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Bialaphos
Bialaphos.svg
Names
IUPAC name
(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl] amino]propanoyl]amino]propanoic acid
Other names
L-Alanyl-L-alanyl-phosphinothricin
Identifiers
CAS number 35597-43-4 YesY
ChemSpider 4575372 YesY
Jmol-3D images Image
PubChem 5462314
Properties
C11H22N3O6P
Molar mass 323.28 g·mol−1
Density 1.33 g/mL
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bialaphos is a natural herbicide produced by the bacteria Streptomyces hygroscopicus[1] and Streptomyces viridochromogenes. Bialaphos is a protoxin and non-toxic as is. When it is metabolized by the plant, the glutamic acid analog L-phosphinothricin is released which inhibits glutamine synthetase. This results in the accumulation of ammonium and disruption of primary metabolism.[2]

Bialaphos is made up of two alanine residues and phosphinothricin and is commonly used as a gene sector in plants. Resistance plasmids include: pGreenII 0229 and pGreenII 0229 62-SK. pGreenII 0229 is derived from pGreenII 0000, a nos-bar cassette has been inserted into the HpaI site of the Left Border, providing resistance to bialaphos or phosphinothricin during plant transformation selection. pGreenII 0229 62-SK is derived from pGreenII 0229, the LacZ blue/white cloning selection has been replaced with a 35S-MCS-CaMV cassette that allows the insertion of a gene of interest into a 35S over-expression cassette.[3]

References[edit]

  1. ^ Murakami, Takeshi; Anzai, Hiroyuki; Imai, Satoshi; Satoh, Atsuyuki; Nagaoka, Kozo; Thompson, Charles J. (1986). "The bialaphos biosynthetic genes of Streptomyces hygroscopicus: Molecular cloning and characterization of the gene cluster". MGG Molecular & General Genetics 205: 42. doi:10.1007/BF02428031. 
  2. ^ Duke, Stephen O.; Dayan, Franck E. (2011). "Modes of Action of Microbially-Produced Phytotoxins". Toxins (Basel) 3: 1038. doi:10.3390/toxins3081038. 
  3. ^ "Bialaphos as plant gene selector". Retrieved 20 June 2012.