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An improved synthesis of guanosine TNA phosphoramidite for oligonucleotide synthesis

Year: 2024

Type: article

Abstract: The chemical synthesis of guanosine nucleosides generates both the N9 and N7 regioisomers, which require careful separation to obtain the desired N9 isomer. To preferentially obtain the N9 isomer, a bulky diphenylcarbamoyl (DPC) group can be installed at the O6 position of guanine. However, installation of the DPC group presents a challenging task due to low solubility of the N-acetyl protected guanine. Here we report the usage of commercially available 2-amino-6-chloro purine as a new strategy that offers a more efficient route to the synthesis of the guanine phosphoramidite of threose nucleic acid (TNA).

Source: Nucleosides Nucleotides & Nucleic Acids

DOI: 10.1080/15257770.2024.2369688

Authors: Biju Majumdar, Daisy Sarma, Erica M. Lee, Noah A. Setterholm, John C. Chaput

Institutions: University of California, Irvine, University of California System

Language: English

Topic: DNA and Nucleic Acid Chemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

OpenAlex ID: W4399895588

FWCI:

Cites: 15

Cited by:

Related to: 10