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US 2011/0257047 A1Published application
Methods for Labeling a Substrate Using a Hetero-Diels-Alder Reaction
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorsVladimir V. Popik, Selvanathan Arumugam
Life of this patent
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Abstract
Methods for labeling a substrate using a hetero-Diels-Alder reaction are disclosed. The hetero-Diels-Alder reaction includes the reaction of an o-quinone methide (e.g., an o-naphthoquinone methide) with a polarized olefin to form a hetero-Diels-Alder adduct. The o-quinone methide or the polarized olefin can be attached to a surface of a substrate, and the other of the o-quinone methide or the polarized olefin can include a detectable label. The o-quinone methide can conveniently be generated by irradiation of a precursor compound, preferably in an aqueous solution, suspension, or dispersion.
Claims33
A method for labeling a substrate, the method comprising:
- generating an o-quinone methide attached to a surface of a substrate and having the formula:
- and
- contacting the o-quinone methide with a polarized olefin having the formula:
- under conditions effective to form a hetero-Diels-Alder adduct,
- wherein:
- each R1 is independently H, halogen, or an organic group, with the proviso that at least one R1 comprises a linker group attached to the surface of the substrate;
- each R2 is independently H or an organic group;
- each R3 is independently H, halogen, or an organic group;
- X is O or NR4, wherein R4 is H or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- optionally, two or more R2 groups may be combined to form one or more rings;
- optionally, two or more R3 and/or R4 groups may be combined to form one or more rings;
- and
- with the proviso that at least one R2, R3, or R4 comprises a detectable label.
11 more elements
A method for labeling a substrate, the method comprising:
- providing a precursor compound attached to a surface of a substrate and having the formula:
- irradiating the precursor compound under conditions effective to form an o-quinone methide having the formula:
- and
- contacting the o-quinone methide with a compound having the formula
- under conditions effective to form a hetero-Diels-Alder adduct,
- wherein:
- each R1 is independently H, halogen, or an organic group, with the proviso that at least one R1 comprises a linker group attached to the surface of the substrate;
- each R2 is independently H or an organic group;
- each R3 is independently H, halogen, or an organic group;
- X is O or NR4;
- Y is OR5, NR52, NR53+(Z1/q)− wherein Z is an anion having a negative charge of q;
- each R5 is independently H or an organic group,
- optionally, two or more R1 groups may be combined to form one or more rings;
- optionally, two or more R2 groups may be combined to form one or more rings;
- optionally, two or more R3 and/or R4 groups may be combined to form one or more rings;
- optionally, two or more R5 groups may be combined to form one or more rings;
- and
- with the proviso that at least one R2, R3, or R4 comprises a detectable label.
15 more elements
A method for labeling a substrate, the method comprising:
- generating an o-quinone methide having the formula:
- and
- contacting the o-quinone methide with a polarized olefin attached to a surface of a substrate and having the formula:
- under conditions effective to form a hetero-Diels-Alder adduct,
- wherein:
- each R1 is independently H, halogen, or an organic group, with the proviso that at least one R1 comprises a detectable label;
- each R2 is independently H or an organic group;
- each R3 is independently H, halogen, or an organic group;
- X is O or NR4, wherein R4 is H or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- optionally, two or more R2 groups may be combined to form one or more rings;
- optionally, two or more R3 and/or R4 groups may be combined to form one or more rings;
- and
- with the proviso that at least one R2, R3, or R4 comprises a linker group attached to the surface of the substrate.
11 more elements
A method for labeling a substrate, the method comprising:
- providing a precursor compound having the formula:
- irradiating the precursor compound under conditions effective to form an o-quinone methide having the formula:
- and
- contacting the o-quinone methide with a polarized olefin attached to a surface of a substrate and having the formula:
- under conditions effective to form a hetero-Diels-Alder adduct,
- wherein:
- each R1 is independently H, halogen, or an organic group, with the proviso that at least one R1 comprises a detectable label;
- each R2 is independently H or an organic group;
- each R3 is independently H, halogen, or an organic group;
- X is O or NR4;
- Y is OR5, NR52, NR53+(Z1/q)− wherein Z is an anion having a negative charge of q;
- each R5 is independently H or an organic group;
- optionally, two or more R1 groups may be combined to foam one or more rings;
- optionally, two or more R2 groups may be combined to form one or more rings;
- optionally, two or more R3 and/or R4 groups may be combined to form one or more rings;
- optionally, two or more R5 groups may be combined to form one or more rings;
- and
- with the proviso that at least one R2, R3, or R4 comprises a linker group attached to the surface of the substrate.
15 more elements
A precursor compound having the foiinula:
- wherein:
- each R1 is independently H, halogen, or an organic group;
- Y is OR5, NR52, NR53+(Z1/q)− wherein Z is an anion having a negative charge of q;
- each R5 is independently H or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- optionally, two or more R5 groups may be combined to form one or more rings;
- and
- with the proviso that at least one R1 comprises a detectable label or a linker group attached to a surface of a substrate.
5 more elements
An o-quinone methide having the formula:
- wherein each R1 is independently H, halogen, or an organic group, with the proviso that at least one R1 comprises a detectable label or a linker group attached to a surface of a substrate;
- and wherein optionally two or more R1 groups may be combined to form one or more rings.
Dependencies are inferred from the claim text.