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Bialaphos

Bialaphos
Names
Systematic IUPAC name
(2S)-2-[(2S)-2-{(2S)-2-Amino-4-[hydroxy(methylphosphonoyl)]butanamido}propanamido]propanoic acid
Other names
L-Alanyl-L-alanyl-phosphinothricin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.113.731 Edit this at Wikidata
UNII
  • 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 checkY
    Key: GINJFDRNADDBIN-FXQIFTODSA-N checkY
  • 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
  • O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCP(=O)(O)C)C)C
Properties
C11H22N3O6P
Molar mass 323.286 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).

Bialaphos is a natural herbicide produced by the bacteria Streptomyces hygroscopicus[1] and Streptomyces viridochromogenes. It is also known by the ISO common name bilanafos.[2] Bialaphos is a protoxin and nontoxic as is. When it is metabolized by a plant, the glutamic acid analog glufosinate is released which inhibits glutamine synthetase. This results in the accumulation of ammonium and disruption of primary metabolism.[3]

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.[4]

See also

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References

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  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: 42–53. doi:10.1007/BF02428031. S2CID 32983239.
  2. ^ "Compendium of Pesticide Common Names: Bilanafos". BCPC. Retrieved 2024-05-07.
  3. ^ Duke, Stephen O.; Dayan, Franck E. (2011). "Modes of Action of Microbially-Produced Phytotoxins". Toxins (Basel). 3 (8): 1038–1064. CiteSeerX 10.1.1.288.3457. doi:10.3390/toxins3081038. PMC 3202864. PMID 22069756.
  4. ^ "Bialaphos as plant gene selector" (PDF). Archived from the original (PDF) on 21 October 2014. Retrieved 20 June 2012.