US6114518A
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US
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Synthesis and use of labelled phosphoramidite compositions
Assignee: Becton Dickinson and Co
•
Filing: 1999-09-30
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Granted: 2000-09-05
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Expires: 2019-09-30
Abstract
Abstract The present invention provides labelled phosphoramidite compositions, methods for making these labelled phosphoramidite compositions, and methods for using these labelled phosphoramidite compositions for labelling oligonucleotides. Even more particularly, the present invention provides compositions and methods for labeling the 5' end of oligonucleotides during synthesis of the oligonucleotides.
Inventors
- 👤 J. Bruce Pitner
- 👤 C. Preston Linn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 20:37
CPC Classifications
C; C07; C07H; C07H21/00; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/22; C07F9/24; C07F9/2404; C07F9/2408
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
100 words
A composition comprising: ##STR22## wherein X is SO 2 , CO, or CS; R 1 and R 2 are the same or different and are an alkyl group from 1 to 6 carbons in length or can jointly form with N to form a 5 or 6-membered cyclic ring, wherein the ring optionally contains oxygen; R 3 and R 4 are the same or different, and are an alkyl group from 1 to 10 carbons in length, or isopropyl; n is an integer from 1 to 10, and R 6 is (CH 2 ) 2 CN or CH 3 .
Claim 2
Dependent Claim
100 words
A composition comprising: ##STR22## wherein X is SO 2 , CO, or CS; R 1 and R 2 are the same or different and are an alkyl group from 1 to 6 carbons in length or can jointly form with N to form a 5 or 6-membered cyclic ring, wherein the ring optionally contains oxygen; R 3 and R 4 are the same or different, and are an alkyl group from 1 to 10 carbons in length, or isopropyl; n is an integer from 1 to 10, and R 6 is (CH 2 ) 2 CN or CH 3 .
Claim 3
Dependent Claim
7 words
The composition of claim 1, comprising: ##STR23##
Claim 4
Dependent Claim
85 words
The composition of claim 1, selected from the group consisting of: wherein R 1 and R 2 are the same or different and are an alkyl group from 1 to 6 carbons in length or can jointly form with N a 5 or 6-membered cyclic ring, wherein the ring optionally contains oxygen; R 3 and R 4 are the same or different and are isopropyl or an alkyl group from 1 to 10 carbons in length; and n is an integer from 1 to 10.
Claim 5
Dependent Claim
42 words
The composition of claim 1, wherein X is SO 2 , R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is an integer from 2 to 8.
Claim 6
Dependent Claim
37 words
The composition of claim 1, wherein X is SO 2 , R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is 4.
Claim 7
Dependent Claim
40 words
The composition of claim 1, wherein X is CO, R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is an integer from 2 to 8.
Claim 8
Dependent Claim
35 words
The composition of claim 1, wherein X is CO, R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is 4.
Claim 9
Dependent Claim
40 words
The composition of claim 1, wherein X is CS, R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is an integer from 2 to 8.
Claim 10
Dependent Claim
35 words
The composition of claim 1, wherein X is CS, R 1 and R 2 are the same or different and are methyl or ethyl, R 3 and R 4 are isopropyl and n is 4.
Claim 11
Dependent Claim
7 words
The composition of claim 7 comprising ##STR24##
Claim 12
Dependent Claim
6 words
The composition of claim 5 comprising
Claim 13
Dependent Claim
6 words
The composition of claim 9 comprising
Claim 14
Independent Claim
44 words
A method of preparing a labelled phosphoramidite composition comprising the steps of: a) reacting DABSYL, DABCYL thioamide or DABCYL with an amino-containing alkyl alcohol to produce a reaction product; and b) reacting the reaction product with a phosphoramidite to produce a labelled phosphoramidite composition.
Claim 15
Independent Claim
44 words
A method of preparing a labelled phosphoramidite composition comprising the steps of: a) reacting DABSYL, DABCYL thioamide or DABCYL with an amino-containing alkyl alcohol to produce a reaction product; and b) reacting the reaction product with a phosphoramidite to produce a labelled phosphoramidite composition.
Claim 16
Dependent Claim
14 words
The method of claim 13 wherein the label is DABSYL, DABCYL thioamide or DABCYL.
Claim 17
Dependent Claim
12 words
The method of claim 13 wherein the amino-containing alkyl alcohol is 6-amino-l-hexanol.
Claim 18
Dependent Claim
11 words
The method of claim 13 wherein the phosphoramidite is N, N-Diisopropylchloro-β-cyanoethyl-phosphoramidite.
Claim 19
Independent Claim
48 words
A method of preparing a labelled phosphoramidite composition comprising the steps of: a) reacting a label, wherein the label is DABSYL, DABCYL thioamide or DABSYL, with 6-amino-l-hexanol to produce a reaction product; and b) reacting the reaction product with a N, N-Diisopropylchloro-β-cyanoethyl-phosphoramidite to produce a labelled phosphoramidite composition.
Claim 20
Independent Claim
48 words
A method of preparing a labelled phosphoramidite composition comprising the steps of: a) reacting a label, wherein the label is DABSYL, DABCYL thioamide or DABSYL, with 6-amino-l-hexanol to produce a reaction product; and b) reacting the reaction product with a N, N-Diisopropylchloro-β-cyanoethyl-phosphoramidite to produce a labelled phosphoramidite composition.
Claim 21
Dependent Claim
65 words
A method of preparing labelled oligonucleotides using the labelled phosphoramidite composition of claim 1, comprising the steps of: a) synthesizing an oligonucleotide from a 3' end of the oligonucleotide; b) adding the labelled phosphoramidite to the oligonucleotide when a last base is added to a 5' end of the oligonucleotide; c) de-protecting the oligonucleotide to form a deprotected product; and d) recovering the deprotected product.
Claim 22
Dependent Claim
12 words
The method of claim 18, wherein the labelled phosphoramidite composition is ##STR25##20.
Claim 23
Dependent Claim
11 words
The method of claim 18, wherein the labelled phosphoramidite composition is
Claim 24
Dependent Claim
11 words
The method of claim 18, wherein the labelled phosphoramidite composition is
Claim 25
Dependent Claim
32 words
A method for detecting a target nucleic acid comprising the step of hybridizing to the target nucleic acid a probe labelled at a 5' end with a composition according to claim 1.
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