# US 5,703,218 A · Oligonucleotides containing hydroxyl-protecting groups orthogonally removable by reduction

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,703,218 A
- Document ID: US5703218A
- Status: Granted
- Kind: A
- Application number: 08/421,798
- Filed: 1995-04-13
- Granted: 1997-12-30
- Earliest claimed: 1990-07-27
- Assignees: Chiron Corporation
- Inventors: Michael S. Urdea; Thomas Horn
- Web page: https://patentgrep.com/patent/US5703218A

## CPC

- C07H 19/10: with the saccharide radical esterified by phosphoric or polyphosphoric acids
- 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
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Hydroxyl-protecting groups orthogonally removable by reduction with a liquid reducing agent are disclosed. The novel hydroxyl-protecting groups are particularly useful in the chemical synthesis of linear and branched oligonucleotide structures, as they are readily removed from the protected molecule with mild reagents such as dithionite. Examples of such hydroxyl-protecting groups include the 2-methylene-9,10-anthraquinone (Maq) carbonate ester and the p-nitrobenzyl carbonate ester.

## Claims

### Claim 1

An oligonucleotide chain in which from one to all of the nucleotide residues have the structural formula ##STR8## wherein: R is selected from the group consisting of ##STR9## R' is hydrogen or phenyl; R.sup.3 is selected from the group consisting of hydrogen, methyl, I, Br and F;
R.sup.4 is hydrogen or methyl; and
Z is selected from the group consisting of ##STR10## wherein x and y may be the same or different and are integers in the range of 1 to 8 inclusive.

### Claim 2 (depends on 1)

The oligonucleotide chain of claim 1 wherein R is ##STR11##

### Claim 3 (depends on 1)

The oligonucleotide chain of claim 1 wherein R has the structure: ##STR12##

### Claim 4 (depends on 3)

The oligonucleotide chain of claim 3 wherein R' is hydrogen.

### Claim 5 (depends on 3)

The oligonucleotide chain of claim 3 wherein R' is phenyl.