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US 5,512,667 AGranted
Trifunctional intermediates for preparing 3'-tailed oligonucleotides
OwnerMichael W. Reed, Rich B. Meyer, Jr.inventors
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OwnerMichael W. Reed, Rich B. Meyer, Jr.inventors
Estimating the term…
Oligonucleotides having a low molecular weight tail molecules joined to the 3' terminus of the oligonucleotide via a linking molecule of the structure: Z is ##STR1## wherein ##STR2## m and m' are positive integers less than 11, n is 0 or 1 and Q is a connecting group, are synthesized by selectively reacting three independent functional groups on the linking molecule, i.e., an amine, a primary hydroxyl and a secondary hydroxyl, in a stepwise manner. A tail molecule R is first connected to the amino functionality of the linking molecule. Next the linking molecule-tail molecule combination is attached to a solid state support via the secondary hydroxyl group. The oligonucleotide is systematically stepwise synthesized beginning on the primary hydroxyl group followed by release of the oligonucleotide having the low molecular weight tailed joined to its 3' terminus from the solid state support.
A compound having the formula shown below:
A compound having the structure:
A compound of claim, 5 wherein R is selected from the group consisting of cholesterol, biotin, acridine, fluorescein, rhodamine, Lissamine rhodamine B, Malachite Green, erythrosin, tetramethylrhodamine, eosin, pyrene, anthracene, 4-dimethylaminonapthalene, 2-dimethylaminonaphthalene, 7-dimethylamino-4-methylcoumarin, 7-dimethylaminocoumarin, 7-hydroxy-4-methylcoumarin, 7-hydroxycoumarin, 7-methoxycoumarin, 7-acetoxycoumarin, 7-diethylamino-3-phenyl-4-methylcoumarin, isoluminol, benzophenone, dansyl, dabsyl, mansyl, sulforhodamine, 4-acetamido-4-stilbene-2,2'-disulfonic acid disodium salt, 4-benzamido-4'-stilbene-2,2'-disulfonic acid disodium salt, ellipticine, methidium, ethydium, phenanthroline, 2-hydroxyethanethiolato-2,2', 2"-terpyridine-platinium-(II), quinoxaline, an EDTA ligand for attaching Fe and a phenanthroline ligand for attaching Cu.
A compound of the structure:
Dependencies are inferred from the claim text.