Short pendant arm linkers for nucleotides in sequencing applications

• US 10,526,648 B2
• Filed: 07/11/2018
• Issued: 01/07/2020
• Est. Priority Date: 07/12/2017
• Status: Active Grant

• Current Assignee: Illumina Cambridge Limited (Illumina Incorporated)
• Original Assignee: Illumina Cambridge Limited (Illumina Incorporated)
• Inventors: Cressina, Elena, Francais, Antoine, Liu, Xiaohai
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US16/033,118
• Publication Number:
  US 20190017111A1
• Time in Patent Office: 545 Days
• Field of Search: 536 41, 536 231, 435 61
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/073 with 2-deoxyribosyl as the saccharide radical
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/14 Pyrrolo-pyrimidine radicals
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 21/00 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 Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: C12Q 1/6809 Methods for determination or identification of nucleic acids involving differential detection
• CPC Class Codes: C12Q 1/6816 characterised by the detection means C12Q1/6804 takes precedence
• CPC Class Codes: C12Q 1/6869 Methods for sequencing
• CPC Class Codes: C12Q 2525/117 incorporating modified base
• CPC Class Codes: C12Q 2535/122 Massive parallel sequencing

Abstract

The present disclosure relates to new nucleotide and oligonucleotide compounds and their use in nucleic acid sequencing applications.

Claims

1. A compound of the formula (I):

2. The compound according to claim 1, wherein B is a nucleotide base.

3. The compound according to claim 2, wherein B is a pyrimidine base.

4. The compound according to claim 3, wherein the compound is of formula (c) or formula (t):

5. The compound according to claim 2, wherein B is a 7-deazapurine base.

6. The compound according to claim 5, wherein the compound is of formula (a):

7. The compound according to claim 2, wherein the compound is attached to an oligonucleotide.

8. An oligonucleotide labelled with a compound according to claim 2.

18. A kit comprising two or more nucleotides wherein at least one nucleotide is a labelled nucleotide according to claim 2.

19. The kit according to claim 18, comprising two or more nucleotides wherein at least two nucleotides are labelled nucleotides according to claim 2.

20. The kit according to claim 18, comprising four nucleotides wherein at least two nucleotides are labelled nucleotides according to claim 2.

21. The nucleotide according to claim 2, for use in sequencing, expression analysis, hybridization analysis, genetic analysis, RNA analysis, or protein binding assays, or combinations thereof.

22. The oligonucleotide according to claim 8, for use in sequencing, expression analysis, hybridization analysis, genetic analysis, RNA analysis, or protein binding assays, or combinations thereof.

9. A compound of the formula (II):

10. The compound according to claim 9, wherein B is a pyrimidine base.

11. The compound according to claim 10, wherein the compound is of formula (ci) or formula (ti):

12. The compound according to claim 9, wherein B is a 7-deazapurine base.

13. The compound according to claim 12, wherein the compound is of formula (ai):

14. An oligonucleotide comprising a compound according to claim 9.

15. An oligonucleotide comprising two or more copies of a compound according to claim 9.

16. An oligonucleotide comprising ten or more copies of a compound according to claim 9.

17. An oligonucleotide comprising one hundred or more copies of a compound according to claim 9.

23. The oligonucleotide according to claim 14, for use in sequencing, expression analysis, hybridization analysis, genetic analysis, RNA analysis, or protein binding assays, or combinations thereof.