N.sup.4 - acylated cytidinyl compounds useful in oligonucleotide synthesis

• US 5,428,148 A
• Filed: 04/24/1992
• Issued: 06/27/1995
• Est. Priority Date: 04/24/1992
• Status: Expired due to Term

• Current Assignee: Beckman Instruments, Inc. (Danaher Corporation)
• Original Assignee: Beckman Instruments, Inc. (Danaher Corporation)
• Inventors: Reddy, Parameswara M., Hanna, Naeem B.
• Primary Examiner(s): Rollins, John W.
• Assistant Examiner(s): CRANE, LAWRENCE E
• Application Number:
  US07/873,330
• Time in Patent Office: 1,159 Days
• Field of Search: 536/28.51, 536/25.31, 536/26.8, 536/25.3
• US Class Current: 536/26.8
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• 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: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Disclosed herein are protecting groups for exocyclic amino groups of the bases adenine, guanine and cytosine for use in the synthesis of oligonucleotides, the protecting groups being represented by the formula: --CO-- (CH₂)_0-9 --CH₃. In a particularly preferred embodiment, the base cytosine is protected with acetyl (--CO--CH₃), and the oligonucleotide incorporating said protected cytosine is subjected to a cleavage/deprotection reagent comprising at least one straight chain alkylamine having from 1 to about 10 carbon atoms.

Claims

1. A compound having the structure:

##STR6## where "A" is a whole number between 0 and about 9;

X is a phosphoramidite functionality capable of reacting with unblocked 3'"'"'-OH or 5'"'"'-OH of oligonucleosides; and

D is selected from the group consisting of hydrogen, a trityl protecting group, and a pixyl protecting group.

2. The compound of claim 1 wherein A is a whole number between 0 and 5.

3. The compound of claim 1 wherein A is a whole number between 0 and 2.

4. The compound of claim 1 wherein A is 0.

5. A compound having the following structure:

##STR7## where X is a phosphoramidite functionality capable of reacting with unblocked 3'"'"'-OH or 5'"'"'-OH of oligonucleosides and D is selected from the group consisting of hydrogen and a trityl protecting group.