Chemical synthesis and properties of modified oligonucleotides containing 5'-amino-5'-deoxy-5'-hydroxymethylthymidine residues

Bioorganic & Medicinal Chemistry
Akihiro OhkuboTakashi Kanamori

Abstract

In this study, we designed 5'-amino-5'-deoxy-5'-hydroxymethylthymidine as a new oligonucleotide modification with an amino group directly attached to the 5'-carbon atom. We successfully synthesized two isomers of 5'-amino-5'-deoxy-5'-hydroxymethylthymidine via dihydroxylation of the 5'-vinyl group incorporated into 5'-deoxy-5'-C-methenylthymidine derivative. Moreover, it was found that the nuclease resistance, binding selectivity to single-stranded RNA, and triplex-forming ability of an oligonucleotide containing RT residues of the new compound were higher than those of the unmodified oligonucleotide.

References

Dec 1, 1991·Pharmacology & Therapeutics·C A SteinL Yakubov
Dec 1, 1988·Proceedings of the National Academy of Sciences of the United States of America·P S FreemontT A Steitz
Apr 17, 1999·Bioorganic & Medicinal Chemistry Letters·G WangZ Pietrzkowski
Dec 10, 1999·Proceedings of the National Academy of Sciences of the United States of America·M TeplovaM Egli
Feb 14, 2003·Organic Letters·Thazha P PrakashMuthiah Manoharan
Feb 27, 2003·Journal of the American Chemical Society·Andrei P Guzaev, Muthiah Manoharan
Jul 11, 2003·Nucleic Acids Research·David SheehanDouglas J Dellinger
Jul 23, 2003·Human Molecular Genetics·Bianca L GebskiStephen D Wilton
Nov 19, 2005·The Journal of Organic Chemistry·Tetsuya Kodama, Marc M Greenberg
Dec 11, 2007·Nucleosides, Nucleotides & Nucleic Acids·S M Abdur RahmanTakeshi Imanishi
Feb 11, 2015·Chemical Communications : Chem Comm·Stefan MiltonRoger Strömberg
May 24, 2018·Bioorganic & Medicinal Chemistry·Kana KoizumiYoshihito Ueno
Jun 13, 2018·Cold Spring Harbor Perspectives in Biology·Evangelos D Karousis, Oliver Mühlemann
Apr 18, 2019·Nature Reviews. Molecular Cell Biology·Tatsuaki KurosakiLynne E Maquat

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.