Process research on the preparation of DMT protected 2'-O-methoxyethylguanosine for oligonucleotide synthesis in therapeutic applications

Shabbir Ali S Taj; S Narayanan; S Suman Meenakshi; Yogesh S Sanghvi; Bruce S Ross; Vasulinga T Ravikumar

doi:10.1080/15257770802271748

Process research on the preparation of DMT protected 2'-O-methoxyethylguanosine for oligonucleotide synthesis in therapeutic applications

Nucleosides Nucleotides Nucleic Acids. 2008 Sep;27(9):1024-33. doi: 10.1080/15257770802271748.

Authors

Shabbir Ali S Taj¹, S Narayanan, S Suman Meenakshi, Yogesh S Sanghvi, Bruce S Ross, Vasulinga T Ravikumar

Affiliation

¹ Isis Pharmaceuticals, Inc., Carlsbad, California, USA.

PMID: 18711665
DOI: 10.1080/15257770802271748

Abstract

An optimized process to synthesize DMT protected 2 '-O-methoxyethylguanosine is described. A key step involves the enzymatic deamination of a mixture of alkylated products to selectively afford the desired material without resorting to chromatography for purification. This approach was scaled up to kilogram quantities for use in oligonucleotide therapeutics. [Formula: see text].

Publication types

Comparative Study

MeSH terms

Adenosine Deaminase / chemistry
Chromatography, High Pressure Liquid
Gene Expression Regulation / genetics*
Guanosine / analogs & derivatives*
Guanosine / chemical synthesis
Mass Spectrometry
Molecular Structure
Oligonucleotides / chemical synthesis*
Oligonucleotides / genetics

Substances

2'-O-methoxyethylguanosine
Oligonucleotides
Guanosine
Adenosine Deaminase