An herbicide used in plant molecular biology
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Bialaphos (sodium salt)

Item No. 16754

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-alanine, monosodium salt
CAS Number
71048-99-2
Synonyms
  • SF 1293
Molecular Formula
C11H21N3O6P • Na
Formula Weight
345.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
[O-]C([C@H](C)NC([C@H](C)NC([C@@H](N)CCP(C)(O)=O)=O)=O)=O.[Na+]
InChi Code
InChI=1S/C11H22N3O6P.Na/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);/q;+1/p-1/t6-,7-,8-;/m0./s1
InChi Key
RTWIRLHWLMNVCC-WQYNNSOESA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $68

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    10 mg

    $118

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    50 mg

    $387

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    100 mg

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    Cayman Chemical
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    Product Description

    Bialaphos is a natural non-selective phytotoxin produced by certain Streptomyces species. It is a pro-toxin, a tripeptide that is converted in vivo to the active agent phosphinothricin, which is a glutamine analog.1 L-Phosphinothricin inhibits glutamine synthetase (Ki = 6.1 µM), resulting in accumulation of ammonium and disruption of primary metabolism.1,2 The bacterial bar gene encodes a phosphinothricin acetyltransferase, which confers resistance to phosphinothricin.3 Bialaphos is used in the selection of transgenic plants that express the bar gene, usually under the control of a constitutively active viral promoter.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duke, S.O., and Dayan, F.E. Modes of action of microbially-produced phytotoxins. Toxins (Basel) 3(8), 1038-1064 (2011).

    2. Ericson, M.C. Purification and properties of glutamine synthetase from spinach leaves. Plant Physiol. 79(4), 923-927 (1985).

    3. Block, M.D., Botterman, J., Vandewiele, M., et al. Engineering herbicide resistance in plants by expression of a detoxifying enzyme. EMBO J. 6(9), 2513-2518 (1987).