N-4 modified pyrimidine deoxynucleotides and oligonucleotide pro

Details N-4 modified pyrimidine deoxynucleotides and oligonucleotide pro N-4 modified pyrimidine deoxynucleotides and oligonucleotide pro

1994-08-25

1996-12-03

Jones, W. Gary

Chemistry: molecular biology and microbiology

Measuring or testing process involving enzymes or...

Involving nucleic acid

435 5, 435 911, 536 243, 536 2431, 536 2432, 536 2433, C12Q 168, C12Q 170, C12P 1934, C07H 2104

Patent

active

055807313

ABSTRACT:
Novel N-4 modified pyrimidine analogs are provided having the structure (I) or (II) ##STR1## wherein: R.sup.1 is selected from the group consisting of hydrogen, acid-sensitive, base-stable blocking groups and acyl capping groups; R.sup.2 is lower alkyl; R.sup.3 is C.sub.1 -C.sub.12 alkylene containing 0 to 6 linkages selected from the group consisting of --0--, --S-- and --NH--; R.sup.4 is ##STR2## in which R.sup.9 is hydrogen or an optionally substituted aliphatic group; R.sup.10 and R.sup.11 are hydrocarbyl or together form a mono- or polyheterocyclic ring; R.sup.5 is hydrogen or lower alkyl; R.sup.6 is selected from the group consisting of hydrogen, methyl, bromo and iodo; R.sup.7 is C.sub.1 -C.sub.12 alkylene containing 0 to 6 linkages selected from the group consisting of --O--, --S-- and --NR.sup.12 -- wherein R.sup.12 is hydrogen or lower alkyl; and R.sup.8 is a protecting group that can be removed and replaced by reduction. Synthetic methods for preparing the compounds are provided as well, as are methods for making and using polynucleotide probes containing the novel pyrimidine analogs.

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