Nucleosides useful in the preparation of polynucleotides

• US 4,500,707 A
• Filed: 03/16/1982
• Issued: 02/19/1985
• Est. Priority Date: 02/29/1980
• Status: Expired due to Term

• Current Assignee: University Patents, Inc.
• Original Assignee: University Patents, Inc.
• Inventors: Caruthers, Marvin H., Matteucci, Mark D.
• Primary Examiner(s): Hazel, Blondel
• Application Number:
  US06/358,877
• Time in Patent Office: 1,071 Days
• Field of Search: 536/27, 536/28, 536/29, 424/180, 424/176, 424/361
• US Class Current: 536/25.34
• CPC Class Codes: B01J 19/0046 Sequential or parallel reactions, e.g. for the synthesis of polypeptides or polynucleotides; Apparatus and devices for combinatorial chemistry or for making molecular arrays synthesis methods per se C40B50/00
• CPC Class Codes: B01J 2219/00286 Reactor vessels with top and bottom openings
• CPC Class Codes: B01J 2219/00389 Feeding through valves
• CPC Class Codes: B01J 2219/005 Beads
• CPC Class Codes: B01J 2219/0059 Sequential processes
• CPC Class Codes: B01J 2219/00596 Solid-phase processes
• CPC Class Codes: B01J 2219/0068 Means for controlling the apparatus of the process
• CPC Class Codes: B01J 2219/00686 Automatic
• CPC Class Codes: B01J 2219/00722 Nucleotides
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C40B 40/06 Libraries containing nucleotides or polynucleotides, or derivatives thereof
• CPC Class Codes: C40B 60/14 for creating libraries
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

New and useful intermediate nucleotides bound to an inorganic polymer support, including the preparation thereof, and processes for the conversion to oligonucleotides which are especially useful for the synthesis of polynucleotides, particularly ribonucleic (RNA) and deoxyribonucleic acids (DNA).

Claims

1. A compound of the formula:

##STR12## wherein B is a nucleoside or deoxynucleoside base;

R is H or a blocking group, A is H or OR;

R'"'"' is a hydrocarbyl radical containing up to 10 carbon atoms and X is a amino group formed by removal of the hydrogen atom from a ring nitrogen of a nitrogen heterocyclic compound which contains unsaturation in the ring structure.

3. The compound according to claim 1 or 2 wherein the amino group is tetrazolyl, nitroimidazolyl or triazolyl.

4. The compound according to claim 1 or 2 wherein B is thymine, cytosine, adenosine, uracil and guanine.

5. The compound according to claim 1 or 2 wherein R is a trityl group.

6. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl or p-anisylphenylmethyl.

8. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R'"'"' is methyl, A is H and X is tetrazolyl.

9. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl, B is thyminyl, R'"'"' is methyl, A is H and X is tetrazolyl.

10. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl, B is 1-cytosinyl, R'"'"' is methyl, A is H and X is tetrazolyl.

11. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R'"'"' is methyl, A is H and X is tetrazolyl.

12. The compound according to claim 1 or 2 wherein R is di-p-anisylphenylmethyl, B is 9-guaninyl, R'"'"' is methyl, A is H and X is tetrazolyl.

13. The compound according to claim 10 wherein B is 1-(N-4-acetylcytosine), 1-(N-benzoylcytosine, or 1-(N-isobutyrylcytosine).

14. The compound according to claim 12 wherein B is 9-(N-6-benzoylguaninyl), 9-(N-6-acetylguaninyl), or 9-(N-6-isobutyrylguaninyl).

15. The compound according to claim 8 wherein B is 9-(N-6-acetyladeninyl) or 9-(N-6-isobutyryladeninyl).

16. The compound according to claim 11 wherein B is 9-(N-6-acetyladeninyl) or 9-(N-6-isobutyryladeninyl).

2. A compound of the formula:

##STR13## wherein B is a nucleoside or deoxynucleoside base;

R is H or a blocking group;

A is H or OR;

R'"'"' is lower alkyl and X is a amino group formed by removal of the H atom of the amino nitrogen of a nitrogen heterocyclic compound.

7. The compound according to claim 2 wherein A is H.