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US 11,440,933 B2Granted
3′ protected nucleotides
AssigneeRoche Sequencing Solutions, Inc.
InventorsFrank Bergmann, Peter Crisalli, Dieter Hiendl, Omid Khakshoor, Meng Taing
Life of this patent
Estimating the term…
Abstract
The present disclosure provides 3′ protected nucleotides, including those 3′ protected nucleotides having a detectable tag. Systems and methods of sequencing nucleic acids using the 3′ protected nucleotides are also disclosed, such as the sequencing of a nucleic acid using a nanopore or the sequencing of a nucleic acid via sequencing-by-synthesis.
Claims20
A nucleotide or a salt thereof of Formula (IIIA):
- wherein
- X is a nucleobase or a tagged nucleobase;
- Y is —O—P(O)(OH)—[O—P(O)(OH)]z—OH or —O—P(O)(OH)—[O—P(O)(OH)]z—O-oligonucleotide, where z is 0 or an integer ranging from 1 to 5;
- R1 is a bond, —CH2—, —C(O)—O—, —C(O)—NRa—, or —C(O)—Rx—;
- R2 and R3 are each independently H, a saturated or unsaturated C1-C6 alkyl group, a C5-C6 aryl or heteroaryl group, a halogen, —[(C(Ra)(Rb))p—O]q (Ra), —C(O)—ORa, —C(O)—N(Ra)(Rb), —(C(Ra)(Rb))n—N+C−, —CN, or —NO2;
- R4 is a bond, a substituted or unsubstituted 5- to 7-membered aryl group, —CH═CH—, a substituted or unsubstituted 5- or 6-membered heterocycloalkyl group, or —O—C(O)-aryl-;
- R5 is —(C(Ra)(Rb))n—N3, —(C(Ra)(Rb))n—N+C−, a 5- to 8-membered cycloalkyl group comprising two sulfur atoms positioned 1, 3 relative to each other, or a group having the structure:
- Z1 and Z2 are independently H, a C1-C4 alkyl group, or a 5- to 6-membered aryl group optionally substituted with one or more hydroxyl groups;
- Q1 and Q3 are each independently a bond, —C(Re)(Rf)—, or —C(O)—;
- Q2 is a bond, o-phenylene, or —[C(Re)(Rf)]w—, where w is 1 or 2;
- Ra and Rb are each independently H or a saturated C1-C6 alkyl group;
- Re and Rf are independently H, methyl, ethyl, isopropyl, or a substituted or unsubstituted 5- or 6-membered aryl group;
- Rx is a substituted or unsubstituted 5- or 6-membered aromatic group or heteroaromatic group;
- n is 0 or an integer ranging from 1 to 3;
- and
- p and q are each independently zero or an integer ranging from 1 to 3;
- provided that when R1 and R4 are both bonds and when R2 and R3 are both H, then R5 is not an azide.
14 more elements
A nucleotide or a salt thereof of Formula (IIIA):
- wherein
- X is a nucleobase or a tagged nucleobase;
- Y is —O—P(O)(OH)—[O—P(O)(OH)]z—OH or —O—P(O)(OH)—[O—P(O)(OH)]z—O-oligonucleotide, where z is 0 or an integer ranging from 1 to 5;
- R1 is a bond, —CH2—, —C(O)—O—, —C(O)—NRa—, or —C(O)—Rx—;
- R2 is H;
- R3 is a saturated or unsaturated C1-C6 alkyl group, a C5-C6 aryl or heteroaryl group, a halogen, —[(C(Ra)(Rb))p—O]q—(Ra), —C(O)—ORa, —C(O)—N(Ra)(Rb), —(C(Ra)(Rb))n—N+C−, —CN, or —NO2;
- R4 is a bond, a substituted or unsubstituted 5- to 7-membered aryl group, —CH═CH—, a substituted or unsubstituted 5- or 6-membered heterocycloalkyl group, or —O—C(O)-aryl-;
- R5 is —(C(Ra)(Rb))n—N3, —(C(Ra)(Rb))n—N+C−, —(C(Ra)(Rb))n—CN, a 5- to 8-membered cycloalkyl group comprising two sulfur atoms positioned 1, 3 relative to each other, or a group having the structure:
- Z1 and Z2 are independently H, a C1-C4 alkyl group, or a 5- to 6-membered aryl group optionally substituted with one or more hydroxyl groups;
- Q1 and Q3 are each independently a bond, —C(Re)(Rf)—, or —C(O)—;
- Q2 is a bond, o-phenylene, or —[C(Re)(Rf)]w—, where w is 1 or 2;
- Ra and Rb are each independently H or a saturated C1-C6 alkyl group;
- Re and Rf are independently H, methyl, ethyl, isopropyl, or a substituted or unsubstituted 5- or 6-membered aryl group;
- Rx is a substituted or unsubstituted 5- or 6-membered aromatic group or heteroaromatic group;
- n is 0 or an integer ranging from 1 to 3;
- and
- p and q are each independently zero or an integer ranging from 1 to 3;
- provided that when R1 and R4 are both bonds and when R2 and R3 are both H, then R5 is not an azide.
15 more elements
A nucleotide or a salt thereof of Formula (IIIA):
- wherein
- X is a nucleobase or a tagged nucleobase
- Y is —O—P(O)(OH)—[O—P(O)(OH)]z—OH or —O—P(O)(OH)—[O—P(O)(OH)]z—O-oligonucleotide, where z is 0 or an integer ranging from 1 to 5;
- R1 is a bond, —CH2—, —C(O)—O—, —C(O)—NRa—, or —C(O)—Rx—;
- R2 and R3 are independently a saturated or unsaturated C1-C6 alkyl group, a C5-C6 aryl or heteroaryl group, a halogen, —[(C(Ra)(Rb))p—O]q (Ra), —C(O)—ORa, —C(O)—N(Ra)(Rb), —(C(Ra)(Rb))n—N+C−, —CN, or —NO2;
- R4 is a bond, a substituted or unsubstituted 5- to 7-membered aryl group, —CH═CH—, a substituted or unsubstituted 5- or 6-membered heterocycloalkyl group, or —O—C(O)-aryl-;
- R5 is —(C(Ra)(Rb))n—N3, —(C(Ra)(Rb))n—N+C−, —(C(Ra)(Rb))n—CN, a 5- to 8-membered cycloalkyl group comprising two sulfur atoms positioned 1, 3 relative to each other, or a group having the structure:
- Z1 and Z2 are independently H, a C1-C4 alkyl group, or a 5- to 6-membered aryl group optionally substituted with one or more hydroxyl groups;
- Q1 and Q3 are each independently a bond, —C(Re)(Rf)—, or —C(O)—;
- Q2 is a bond, o-phenylene, or —[C(Re)(Rf)]w—, where w is 1 or 2;
- Ra and Rb are each independently H or a saturated C1-C6 alkyl group;
- Re and Rf are independently H, methyl, ethyl, isopropyl, or a substituted or unsubstituted 5- or 6-membered aryl group;
- Rx is a substituted or unsubstituted 5- or 6-membered aromatic group or heteroaromatic group;
- n is 0 or an integer ranging from 1 to 3;
- and
- p and q are each independently zero or an integer ranging from 1 to 3;
- provided that when R1 and R4 are both bonds and when R2 and R3 are both H, then R5 is not an azide.
14 more elements
Dependencies are inferred from the claim text.