Home
Resources
Publications
Synthesis of 2-Amino-4-Fluoropyridine-C-Nucleoside Phosphoramidite for Incorporation Into Oligonucleotides

Synthesis of 2-Amino-4-Fluoropyridine-C-Nucleoside Phosphoramidite for Incorporation Into Oligonucleotides

Kousuke Sato, Akira Matsuda

Curr Protoc Nucleic Acid Chem. 2019 Jun;77(1):e77.

PMID: 30747492

Abstract:

Straightforward and efficient methods for the synthesis of 2-amino-4-fluoropyridine-C-nucleoside (dF P) and the solid-phase synthesis of oligodeoxynucleotides containing dF P using a phosphoramidite are described. The synthesis of dF P is achieved by cross-coupling between a nucleobase (2-amino-4-fluoro-3,5-diiodopyridine) and sugar moieties. Its 3'-O-phosphoramidite is obtained by deiodination, 5'-O-protection, and 3'-O-phosphitilation in three steps. The phosphoramidite unit is compatible for the synthesis of oligonucleotides on solid-phase according to conventional phosphoramidite chemistry. The 2-amino-4-fluoropyridine-C-nucleoside moiety incorporated into the oligodeoxynucleotide reacts with a Cys residue in the catalytic site of DNA cytosine-5-methyltransferase (DNMT). It is apparent that 2-amino-4-fluoropyridine-C-nucleoside would be utilized in DNA-protein crosslink technology. This protocol describes the importance of solid-phase synthesis to obtain novel pyridine-C-nucleoside analogues and its incorporation into oligodeoxynucleotides in a short period of time. © 2019 by John Wiley & Sons, Inc.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42411328	DMT-2′O-TBDMS-rU-3-15N phosphoramidite			Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: