Amino acid-derived phosponamidic anhydrides and methods of preparing the same
AssigneeUniversity of Kansas
InventorsKevin T. Sprott, Paul R. Hanson
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Abstract
Phosphonamide compounds and methods of forming those compounds are provided. The inventive methods comprise forming a template opened-ring phosphonamide compound and optionally subjecting the template to a ring-closing metathesis reaction in the presence of a ring-closing catalyst (e.g., a Grubbs catalyst) to yield a heterocyclic phosphonamide. Advantageously, the template structures can be provided with a wide array of functional groups (e.g., amino acid side chains, peptides) chosen to provide particular properties to the compound. The preferred heterocyclic phosphonamides are represented by the formula
Claims20
A compound having a formula selected from the group consisting of
- wherein:
- each X is individually selected from the group consisting of oxygen, —NH, and —NOR1;
- each R1 is individually selected from the group consisting of hydrogen, a 2-15 mer peptide, and an amino acid side chain selected from the group consisting of
- wherein
- each R3 is individually selected from the group consisting of hydrogen, a branched alkyl group, an unbranched alkyl group, a branched alkenyl group, an unbranched alkenyl group, a branched alkynyl group, an unbranched alkynyl group, an allyl group, an aryl group, an acyl group, and a benzyl group;
- and
- each R2 is individually selected from the group consisting of hydrogen, a branched alkyl group, an unbranched alkyl group, a branched alkenyl group, an unbranched alkenyl group, a branched alkynyl group, an unbranched alkynyl group, an allyl group, an aryl group, an acyl group, a 2-15 mer peptide, and a benzyl group.
A method of forming a phosphonamide compound comprising the steps of:
- reacting an allylated compound with a phosphonic compound in order to form an intermediate compound, said allylated compound having the formula
- wherein:
- R1 is selected from the group consisting of hydrogen, a 2-15 mer peptide, and an amino acid side chain selected from the group consisting of
- wherein each R3 is individually selected from the group consisting of hydrogen, a branched alkyl group, an unbranched alkyl group, a branched alkenyl group, an unbranched alkenyl group, a branched alkynyl group, an unbranched alkynyl group, an allyl group, an aryl group, an acyl group, and a benzyl group;
- and
- R2 is selected from the group consisting of hydrogen, a branched alkyl group, an unbranched alkyl group, a branched alkenyl group, an unbranched alkenyl group, a branched alkynyl group, an unbranched alkynyl group, an allyl group, an aryl group, an acyl group, a 2-15 mer peptide, and a benzyl group,
- and said phosphonic compound having the formula R4POY2,
- wherein:
- R4 is selected from the group consisting of hydrogen, a branched alkyl group, an unbranched alkyl group, a branched alkenyl group, an unbranched alkenyl group, a branched alkynyl group, an unbranched alkynyl group, an allyl group, an aryl group, an acyl group, a 2-15 mer peptide, and a benzyl group;
- and
- each Y is individually selected from the group consisting of the halogens;
- and
- dimerizing said intermediate compound to yield the phosphonamide compound.
Dependencies are inferred from the claim text.