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 Number	35597-43-4
3D model (Jmol)	Interactive image
ChemSpider	4575372
ECHA InfoCard	100.113.731
PubChem	5462314
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 Key: GINJFDRNADDBIN-FXQIFTODSA-N 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
SMILES O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCP(=O)(O)C)C)C
Properties
Chemical formula	C11H22N3O6P
Molar mass	323.29 g·mol^−1
Density	1.33 g/mL
Except where otherwise noted, data are 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 nontoxic as is. When it is metabolized by the plant, the glutamic acid analog glufosinate 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 glufosinate, and is commonly used as a selection marker 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 overexpression cassette.^[3]

References

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" (PDF). Retrieved 20 June 2012.