US4973679A
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Process for oligonucleo tide synthesis using phosphormidite intermediates
Assignee: University Patents Inc
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Filing: 1986-09-18
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Granted: 1990-11-27
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Expires: 2006-09-18
Abstract
Abstract A new class of nucleoside phosphoramidites which are relatively stable to permit isolation thereof and storage at room temperature. The phosphoramidites are derivatives of saturated secondary amines.
Inventors
- 👤 Marvin H. Caruthers
- 👤 Serge L. Beaucage
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:39
CPC Classifications
C; C07; C07H; C07H21/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
213 words
In a process for producing oligonucleotides which comprises the step of condensing the 3'-OH or 5'-OH group of a nucleoside or oligonucleotide with a nucleoside phosphite, the improvement being that the nucleoside phosphite is a compound of one of the formulae: ##STR24## wherein B is a nucleoside or deoxynucleoside base; A is H OH or OR 4 in which R 4 is a blocking group; R is a blocking group; R 1 ' is a hydrocarbyl radical containing up to about carbon atoms; and X is NR 2 'R 3 ', wherein R 2 ' and R 3 ' taken separately each represent alkyl, aryl, aralkyl, cycloalkyl and cycloalkylalkyl containing up to 10 carbon atoms; R 2 ' and R 3 ' when taken together form an alkylene chain containing up to 5 carbon atoms in the principal chain and a total of up to 10 carbon atoms with both terminal valence bonds of said chain being attached to the nitrogen atom to which R 2 ' and R 3 ' are attached; and R 2 ' and R 3 ' when taken together with the nitrogen atom to which they are attached form a saturated nitrogen heterocycle including at least one additional heteroatom from the group consisting of nitrogen, oxygen and sulfur.
Claim 2
Dependent Claim
213 words
In a process for producing oligonucleotides which comprises the step of condensing the 3'-OH or 5'-OH group of a nucleoside or oligonucleotide with a nucleoside phosphite, the improvement being that the nucleoside phosphite is a compound of one of the formulae: ##STR24## wherein B is a nucleoside or deoxynucleoside base; A is H OH or OR 4 in which R 4 is a blocking group; R is a blocking group; R 1 ' is a hydrocarbyl radical containing up to about carbon atoms; and X is NR 2 'R 3 ', wherein R 2 ' and R 3 ' taken separately each represent alkyl, aryl, aralkyl, cycloalkyl and cycloalkylalkyl containing up to 10 carbon atoms; R 2 ' and R 3 ' when taken together form an alkylene chain containing up to 5 carbon atoms in the principal chain and a total of up to 10 carbon atoms with both terminal valence bonds of said chain being attached to the nitrogen atom to which R 2 ' and R 3 ' are attached; and R 2 ' and R 3 ' when taken together with the nitrogen atom to which they are attached form a saturated nitrogen heterocycle including at least one additional heteroatom from the group consisting of nitrogen, oxygen and sulfur.
Claim 3
Dependent Claim
12 words
The process according to claim 1 wherein R is a trityl group.
Claim 4
Dependent Claim
11 words
The process according to claim 1 wherein R is a di-p-anisylphenylmethyl.
Claim 5
Dependent Claim
10 words
The process according to claim 1 wherein R is p-anisyldiphenylmethyl.
Claim 6
Dependent Claim
13 words
The process according to claim 1 wherein R 1 ' is lower alkyl.
Claim 7
Dependent Claim
11 words
The process according to claim 1 wherein X is di-lower alkylamino.
Claim 8
Dependent Claim
13 words
The process according to claim 1 wherein X is a saturated nitrogen heterocyclic.
Claim 9
Dependent Claim
15 words
The process according to claim 1 wherein B is adenine, guanine, cytosine, uracil or thymine.
Claim 10
Dependent Claim
25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 ' is methyl, A is H and X is morpholino.
Claim 11
Dependent Claim
24 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is thyminyl, R 1 is methyl, A is H and X is dimethylamino.
Claim 12
Dependent Claim
25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 1-(N-4-benzoylcytosinyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 13
Dependent Claim
25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 14
Dependent Claim
25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-2-isobutyrylguaninyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 15
Dependent Claim
18 words
The process according to claim 1 wherein said nucleoside or oligonucleotide is covalently bonded to an inorganic polymer.
Claim 16
Dependent Claim
23 words
The process according to claim 14 wherein said nucleoside or oligonucleotide is linked to the inorganic polymer through a base hydrolyzable covalent bond.
Claim 17
Dependent Claim
16 words
The process according to claim 15 wherein the base hydrolyzable covalent bond is an ester linkage.
References Cited (Backward Citations)
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