Derivatized macrocycle compound for covalent bonding to a substrate and method of forming and use
OwnerAndrei V. Bordunov, L. Andy Woodruff +1inventors
InventorsAndrei V. Bordunov, L. Andy Woodruff, Christopher A. Pohl
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Abstract
A derivatized macrocyclic compound comprising the formula: 1 wherein M is a molecular framework monocyclic or polycyclic macrocycle moiety; L is a substituted or unsubstituted carbon chain linker covalently bound to M; R is a terminal functional moiety capable of covalent binding to a support substrate Z or of being converted into a functional moiety capable of covalent binding to a support substrate Z such as a resin bead; X and Y are moieties selected from the group consisting of protons, aliphatic groups, aromatic groups, optionally including heteroatoms; and S is sulfur. In one preferred embodiment, M is a cryptand.
Claims28
A derivatized macrocyclic compound comprising the formula:
- 9
- wherein M is a molecular framework monocyclic or polycyclic macrocycle moiety containing at least 12 atoms in each cycle;
- L is a substituted or unsubstituted carbon chain linker covalently bound to M including at least one carbon atom in a structure selected from the group consisting of an aliphatic, aromatic or heterocyclic linker including heteroatoms substituted for hydrogen atoms on the linker;
- R is a terminal functional moiety capable of covalent binding to a support substrate or of being converted into a functional moiety capable of covalent binding to a solid support substrate;
- X and Y are moieties selected from the group consisting of protons, aliphatic groups, aromatic groups, optionally including heteroatoms, substituted for hydrogen atoms in the moieties, selected from the group consisting of oxygen, nitrogen, sulfur, or phosphorus heteroatoms;
- and
- S is sulfur.
A composition comprising a derivatized macrocycle compound covalently bound to a support substrate Z of the following formula:
- 10
- wherein M is a molecular framework monocyclic or polycyclic macrocycle moiety containing at least 12 atoms in each cycle;
- L is a substituted or unsubstituted carbon chain linker covalently bound to M including at least one carbon atom in a structure selected from the group consisting of an aliphatic, aromatic or heterocyclic linker including heteroatoms substituted for hydrogen atoms on the linker;
- R1 is a covalent linker between sulfur atom S and a support substrate Z and comprises a substituted or unsubstituted carbon chain linker including at least one carbon atom in a structure selected from the group consisting of an aliphatic, aromatic or heterocyclic linker including heteroatoms substituted for hydrogen atoms on the linker;
- X and Y are moieties selected from the group consisting of protons, aliphatic groups, aromatic groups, optionally including heteroatoms, substituted for hydrogen atoms in the moieties, selected from the group consisting of oxygen, nitrogen, sulfur, or phosphorus heteroatoms;
- and
- S is sulfur.
A method of making a derivatized macrocycle compound of the formula:
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- wherein M is a molecular framework monocyclic or polycyclic macrocycle moiety containing at least 12 atoms in each cycle;
- L is a substituted or unsubstituted carbon chain linker covalently bound to M including at least one carbon atom in a structure selected from the group consisting of an aliphatic, aromatic or heterocyclic linker, optionally including heteroatoms, substituted for hydrogen atoms on the linker, selected from the group consisting of oxygen, nitrogen, sulfur or phosphorus;
- R is a terminal functional moiety capable of covalent binding to a substrate or of being converted into a functional moiety capable of covalent binding to a substrate;
- X and Y are moieties selected from the group consisting of protons, aliphatic groups, aromatic groups, optionally including heteroatoms, substituted for hydrogen atoms in the moieties, selected from the group consisting of oxygen, nitrogen, sulfur, or phosphorus heteroatoms;
- S is sulfur;
- said method comprising reacting the intermediate compound:
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- with HSR under free radical activation conditions to form said derivatized macrocycle,
- wherein U is a double or triple bond.
Dependencies are inferred from the claim text.