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US 5,212,304 AGranted
Amino-derivatized phosphoramidite linking agents
AssigneeApplied Biosystems, LLC
InventorsSteven Fung, Sam L. Woo, Lloyd M. Smith
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Abstract
The compounds of the invention include novel linking agents comprising 2-substituted-3-protected-1,3,2-oxazaphosphacycloalkanes and their phosphoramidite precursors. The compounds of the invention further include conjugates of the above linking agents with oligonucleotides and polymer supports. The compounds of the present invention are useful for linking organic moieties, such as fluorescent or chromogenic dyes, to polymer supports and oligonucleotides, particularly single- and double-stranded DNA and RNA fragments.
Claims25
A compound of the formula:
- ##STR9## wherein:
- j is in the range of 2 to 10;
- R.sub.1 is an amino protection group;
- R.sub.2 and R.sub.3 taken separately each represent hydrogen;
- alkyl having from 1 to 6 carbon atoms;
- halo-, cyano-, nitro-, sulfo-, halomethyl-, dihalomethyl-, or trihalomethyl-substituted alkyl having from 1 to 6 carbon atoms;
- cycloalkyl having from 3 to 6 carbon atoms;
- cyano, halo, or nitro;
- R.sub.4 is alkyl, alkenyl, aryl, aralkyl, or cycloalkyl containing up to 10 carbon atoms;
- and
- R' and R" taken separately each represent alkyl, aryl, aralkyl, cycloalkyl, or cycloalkylalkyl containing up to 10 carbon atoms;
- or R' and R" 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' and R" are attached;
- or R' and R" when taken together with the nitrogen atom to which they are attached from a hydrogen-saturated nitrogen heterocycle of five or six atoms selected from the group consisting of carbon, nitrogen, oxygen, and sulfur.
10 more elements
A cycloalkane of the formula:
- ##STR10## the cycloalkane having a protected amino substituent and a phosphoramidite substituent wherein:
- s is in the range of 0 to 8, t is in the range of 0 to 8, and s+t is in the range of 1 to 8;
- R.sub.1 is an amino protection group;
- R.sub.4 is alkyl, alkenyl, aralkyl, or cycloalkyl containing up to 10 carbon atoms;
- and
- R' and R" taken separately are alkyls selected from the group consisting of isopropyl, t-butyl, sec-butyl, neopentyl, tert-pentyl, isopentyl, sec-pentyl, isohexyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, neohexyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, and 1-ethyl-2-methylpropyl;
- or R' and R" taken together with the nitrogen atom to which they are attached is morpholino, pyrrolidino, or piperidino.
4 more elements
Dependencies are inferred from the claim text.