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US 5,484,908 AGranted
Oligonucleotides containing 5-propynyl pyrimidines
AssigneeGilead Sciences, Inc.
InventorsBrian Froehler, Robert J. Jones
Life of this patent
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Abstract
Oligonucleotides with enhanced hybridization binding possessing 5-propynyluracil and/or 5-propynylcytosine in place of uracil and cytosine, respectively. These oligonucleotides are useful in traditional hybridization assays for detection of a specific DNA sequence.
Claims18
A nucleoside analog having the general structural formula:
- ##STR14## wherein in each of formula 4 and formula 5 one R.sup.1 is a protecting group and the other is an activated group for oligonucleotide synthesis or is a solid support;
- R.sup.2 is selected from the group consisting of propynyl, 3-buten-1-ynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, propenyl, phenyl, o-pyridinyl, m-pyridinyl and p-pyridinyl;
- and
- R.sup.3 is selected from the group consisting of H, OH, F, OCH.sub.3, OC.sub.2 H.sub.5, OC.sub.3 H.sub.7, SCH.sub.3, SC.sub.2 H.sub.5, SC.sub.3 H.sub.7, OC.sub.3 H.sub.5, and SC.sub.3 H.sub.5.
1 more element
An o-xyloso nucleoside dimer having the general structural formula:
- ##STR15## wherein each R.sup.1 is H or a blocking group;
- and
- each B is independently a purine or pyrimidine base, provided that at least one B is ##STR16## wherein R.sup.2 is selected from the group consisting of propynyl, 3-buten-1-ynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, propenyl, phenyl, o-pyridinyl, m-pyridinyl and p-pyridinyl.
A nucleoside analog dimer having the general structural formula 8:
- ##STR17## wherein X is selected from the group consisting of O and S;
- B is independently a purine or pyrimidine base, provided that at least one B is ##STR18## wherein each R.sup.1 is independently selected from the group consisting of H and a blocking group;
- each R.sup.2 is independently selected from the group consisting of propynyl, 3-buten-1-ynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, propenyl, phenyl o-pyridinyl, m-pryridinyl and p-pyridinyl;
- and
- each R.sup.3 is independently selected from the group consisting of H, OH, F, OCH.sub.3, OC.sub.2 H.sub.5, OC.sub.3 H.sub.7, SCH.sub.3, SC.sub.2 H.sub.5, SC.sub.3 H.sub.7, OC.sub.3 H.sub.5, or SC.sub.3 H.sub.5.
2 more elements
Dependencies are inferred from the claim text.