MetaCyc Compound: bialaphos

Abbrev Name: bialaphos

Synonyms: PTT, phophinothricin tripeptide, phosphinothricylalanylalanine, 2-amino-4-(methylphosphino)butyrylalanylalanine, bilanafos, (2S)-2-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-alanine

Phophinothricin tripeptide (also known as Bialaphos), a product of some strains of Streptomyces, is a unique tripeptide composed of one L-phophinothricin residue (a nonproteinogenic amino acid that contains a C-P-C motif) and two L-alanine residues.

Phophinothricin tripeptide is a non-selective foliar-applied herbicide and has strong herbicidal activities against a wide range of monocotyledonous and dicotyledonous weeds. The active ingredient is the L-phophinothricin residue, which inhibits glutamine synthetase, resulting in ammonia accumulation and inhibition of photosynsesis in plants.

Chemical Formula: C11H21N3O6P

Molecular Weight: 322.28 Daltons

Monoisotopic Molecular Weight: 324.13244699649994 Daltons

bialaphos compound structure

SMILES: CC(C(=O)NC(C)C(=O)[O-])NC(=O)C(CCP(=O)([O-])C)[N+]

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)/p-1/t6-,7-,8-/m0/s1


Unification Links: PubChem:90657547

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 3.5614612Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

phosphinothricin tripeptide biosynthesis :
N-acetyl-phophinothricin tripeptide + H2O → bialaphos + acetate

Created 25-Aug-2009 by Caspi R, SRI International


Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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