Compositions including functional groups coupled to substrates, and methods of making the same

Patent metadata

Field	Value
Publication number	US-12060448-B2
Application number	US-202117565818-A
Country	US
Kind code	B2
Filing date	Dec 30, 2021
Priority date	Jan 5, 2021
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

Abstract

In one example, an unsaturated cyclic dione is coupled to the substrate, and is reacted with an indole or indazole including a first functional group to form a first adduct coupling the first functional group to the substrate. In another example, an unsaturated cyclic dione is coupled to a substrate and reacted with a diene including a functional group to form an adduct coupling the functional group to the substrate. In another example, an indole or indazole is coupled to a substrate, and is reacted with an unsaturated cyclic dione including an oligonucleotide to form an adduct coupling the oligonucleotide to the substrate. In another example, a diene is coupled to a substrate, and is reacted with an unsaturated cyclic dione including an oligonucleotide to form an adduct coupling the oligonucleotide to the substrate.

First claim

What is claimed is:

1. A method of coupling a functional group to a substrate, the method comprising:
providing an unsaturated cyclic dione coupled to a substrate; and
reacting the unsaturated cyclic dione with an indole or indazole including a first functional group to form a first adduct coupling the first functional group to the substrate.

2. The method of claim 1 , wherein the unsaturated cyclic dione is:

where L comprises a linker to the substrate and each X independently is CH or N.

3. The method of claim 2 , wherein the unsaturated cyclic dione is triazolinedione:

4. The method of claim 2 , wherein the unsaturated cyclic dione is maleimide:

5. The method of claim 2 , wherein the unsaturated cyclic dione is 4-cyclopentene-1,3-dione:

6. The method of claims 1 , wherein the indole or indazole is:

where F1 comprises the first functional group; R is H, an electron withdrawing group, or an electron donating group; and Z is CH or N.

7. The method of claim 6 , wherein the indole is 1H-indole:

8. The method of claim 6 , wherein the indole is 1H-indazole:

9. The method of claim 6 , wherein the first adduct is:

where L comprises a linker to the substrate and each X independently is CH or N.

10. The method of claim 9 , wherein the first adduct is:

11. The method of claim 1 , further comprising heating the first adduct to regenerate the cyclic unsaturated dione coupled to the substrate.

12. The method of claim 1 , further comprising reacting the first adduct with a diene including a second functional group to form a second adduct coupling the second functional group to the substrate.

13. The method of claim 12 , wherein the diene comprises a 1,3-diene.

14. The method of claim 13 , wherein the 1,3-diene is:

where F2 comprises the second functional group.

15. The method of claim 14 , wherein the second adduct is:

where L comprises a linker to the substrate.

16. The method of claim 12 , wherein the second functional group is selected from the group consisting of: an oligonucleotide, a hydrophilic molecule, a hydrophilic macromolecule, a catalyst, and a label.

17. The method of claim 16 , wherein the second functional group is an oligonucleotide.

18. The method of claim 1 , wherein the first functional group is selected from the group consisting of: an oligonucleotide, a hydrophilic molecule, a hydrophilic macromolecule, a catalyst, and a label.

19. The method of claim 18 , wherein the first functional group is an oligonucleotide.

20. The method of claim 1 , wherein the substrate comprises a polymer disposed on a solid support.

21. The method of claim 20 , wherein the polymer is functionalized to include polyhedral oligomeric silsesquioxane (POSS).

22. The method of claim 1 , wherein providing the unsaturated cyclic dione coupled to the substrate comprises:
providing a 4-substituted urazole coupled to the substrate; and
oxidizing the 4-substituted urazole to form a triazolinedione.

Assignees

• Illumina Inc
• Illumina Cambridge Ltd

Inventors

• Smith Randall
• George Wayne
• Brown Andrew

Classifications

• C12N2310/51

  in polymeric form, e.g. multimers, concatemers · CPC title

• C12N15/1006

  by means of a solid support carrier, e.g. particles, polymers · CPC title

• C08J7/12

  Chemical modification · CPC title

• C08F283/12

  on to polysiloxanes · CPC title

• C07H21/00

  Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids · CPC title