Phosphonate products and methods
AssigneeThe Board of Trustees of the University of Illinois
InventorsWilliam W. Metcalf, Alexander L. Polidore
Life of this patent
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Abstract
Here we show that P. ananatis produces at least three phosphonates, two of which were purified and structurally characterized. The first, designated pantaphos, was shown to be 2-(hydroxy(phosphono)methyl)maleate; the second, a probable biosynthetic precursor, was shown to be 2-(phosphonomethyl)maleate. Purified pantaphos is both necessary and sufficient for the hallmark lesions of onion center rot. Moreover, when tested against mustard seedlings, the phytotoxic activity of pantaphos was comparable to the widely used herbicides glyphosate and phosphinothricin. Pantaphos was also active against a variety of human cell lines.
Claims41
A composition comprising a compound of Formula I:
- or a salt thereof;
- wherein
- represents single or double bond;
- represents double or single bond, wherein both
- are not double bonds;
- G is XACHOR5, O, C(═O), C(═CH2), CHP(=O)(R6)2, or CXB2;
- XA is absent or O;
- each XB is independently H or halo;
- R1 and R2 are each independently ORA or an amino acid;
- R3 is -C(=O)R7 or a triazole or tetrazole;
- R4 is -C(=O)R8 or a triazole or tetrazole;
- R5 is H, -(C1-C6)alkyl, -(C3-C6)cycloalkyl, aryl, or heteroaryl;
- each R6 is independently ORB or an amino acid;
- R7 and R8 are each independently ORC or an amino acid;
- and
- each RA, R B and RC are independently H, -(C1-C6)alkyl, -(C3-C6)cycloalkyl, aryl, or heteroaryl;
- and
- a non-aqueous fluid, additive or combination thereof.
A compound of Formula I:
- or a salt thereof;
- wherein
- represents single or double bond;
- represents double or single bond, wherein both
- are not double bonds;
- G is XACHOR5, O, C(═O), C(═CH2), CHP(=O)(R6)2, or CXB2;
- XA is absent or O;
- each XB is independently H or halo;
- R1 and R2 are each independently ORA or an amino acid;
- R3 is -C(=O)R7 or a triazole or tetrazole;
- R4 is -C(=O)R8 or a triazole or tetrazole;
- R5 is H, -(C1-C6)alkyl, -(C3-C6)cycloalkyl, aryl, or heteroaryl;
- each R6 is independently ORB or an amino acid;
- R7 and R8 are each independently ORC or an amino acid;
- and
- each RA, RB and RC are independently H, -(C1-C6)alkyl, -(C3-C6)cycloalkyl, aryl, or heteroaryl;
- wherein the compound is not a natural product.
A method for forming 2-(hydroxy(phosphono)methyl)maleic acid:
- or salt thereof, comprising:
- a) isomerizing phosphoenolpyruvate (PEP) to 3-phosphonopyruvate (PnPy);
- b) condensing an acetyl group and PnPy to form phosphonomethylmalate (PMM);
- c) dehydrating PMM to 2-phosphonomethylmaleate;
- and
- d) oxidizing 2-phosphonomethylmaleate to pantaphos;
- wherein each step a)-d) is completed in a vessel.
A nucleic acid molecule comprising hvr operon of Pantoea Sp. and optionally an inducible promoter operably linked to the hvr operon.
Dependencies are inferred from the claim text.