BIOMAT Database Logo BIOMAT Database Logo

A Study on Synthesis and Upscaling of 2'-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis. 2021

Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Department of Biosciences and Nutrition, Karolinska Institutet, Neo, 141 57 Huddinge, Sweden.

2'-O-(N-(Aminoethyl)carbamoyl)methyl-modified 5-methyluridine (AECM-MeU) and 5-methylcytidine (AECM-MeC) phosphoramidites are reported for the first time and prepared in multigram quantities. The syntheses of AECM-MeU and AECM-MeC nucleosides are designed for larger scales (approx. 20 g up until phosphoramidite preparation steps) using low-cost reagents and minimizing chromatographic purifications. Several steps were screened for best conditions, focusing on the most crucial steps such as N3 and/or 2'-OH alkylations, which were improved for larger scale synthesis using phase transfer catalysis (PTC). Moreover, the need of chromatographic purifications was substantially reduced by employing one-pot synthesis and improved work-up strategies.

UI MeSH Term Description Entries
D009841 Oligonucleotides Polymers made up of a few (2-20) nucleotides. In molecular genetics, they refer to a short sequence synthesized to match a region where a mutation is known to occur, and then used as a probe (OLIGONUCLEOTIDE PROBES). (Dorland, 28th ed) Oligonucleotide
D009943 Organophosphorus Compounds Organic compounds that contain phosphorus as an integral part of the molecule. Included under this heading is broad array of synthetic compounds that are used as PESTICIDES and DRUGS. Organophosphorus Compound,Organopyrophosphorus Compound,Organopyrophosphorus Compounds,Compound, Organophosphorus,Compound, Organopyrophosphorus,Compounds, Organophosphorus,Compounds, Organopyrophosphorus
D003562 Cytidine A pyrimidine nucleoside that is composed of the base CYTOSINE linked to the five-carbon sugar D-RIBOSE. Cytosine Ribonucleoside,Cytosine Riboside,Ribonucleoside, Cytosine,Riboside, Cytosine
D014529 Uridine A ribonucleoside in which RIBOSE is linked to URACIL. Allo-Uridine,Allouridine,Allo Uridine

Related Publications

Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
LNA 5'-phosphoramidites for 5'→3'-oligonucleotide synthesis.
November 2010, Organic & biomolecular chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Nucleobase-caged phosphoramidites for oligonucleotide synthesis.
June 2007, Current protocols in nucleic acid chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Synthesis of altritol nucleoside phosphoramidites for oligonucleotide synthesis.
September 2007, Current protocols in nucleic acid chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Synthesis of 5'-Thio-3'-O-ribonucleoside Phosphoramidites.
December 2017, The Journal of organic chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Synthesis of 2'-O-photocaged ribonucleoside phosphoramidites.
January 2015, Nucleosides, nucleotides & nucleic acids,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide synthesis.
November 2002, Bioorganic & medicinal chemistry letters,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Synthesis of 5'-O-phosphoramidites with a photolabile 3'-O-protecting group.
September 2004, Current protocols in nucleic acid chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
Chemical synthesis of RNA sequences with 2'-O-[(triisopropylsilyl)oxy]methyl-protected ribonucleoside phosphoramidites.
February 2002, Current protocols in nucleic acid chemistry,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites.
November 1991, Nucleic acids research,
Kristina Karalė, and Martin Bollmark, and Rouven Stulz, and Dmytro Honcharenko, and Ulf Tedebark, and Roger Strömberg
The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides.
June 1987, Nucleic acids research,
Copied contents to your clipboard!