Bialaphos

Bialaphos
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 Registry Number	35597-43-4^Y
ChemSpider	4575372^Y
InChI InChI=1S/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1^Y Key: GINJFDRNADDBIN-FXQIFTODSA-N^Y InChI=1/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1 Key: GINJFDRNADDBIN-FXQIFTODBR
Jmol-3D images	Image
PubChem	5462314
SMILES O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCP(=O)(O)C)C)C
Properties
Molecular formula	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

↑ 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.
↑ Duke, Stephen O.; Dayan, Franck E. (2011). "Modes of Action of Microbially-Produced Phytotoxins". Toxins (Basel) 3: 1038. doi:10.3390/toxins3081038.
↑ "Bialaphos as plant gene selector" (PDF). Retrieved 20 June 2012.

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