Synthesis of a Cyclic Dinucleotide Analogue with Ambiguous Bases, 5-Aminoimidazole-4-carboxamide

Autor:	Yoshiyuki Tanaka, Noriaki Minakawa, Noriko Tarashima, Yusuke Kumanomido, Katsuyuki Nakashima
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Purine Phosphoramidite Chemistry Stereochemistry medicine.drug_class Organic Chemistry Imidazoles Carboxamide Ribonucleotides Chemical synthesis 5-aminoimidazole chemistry.chemical_compound Phosphodiester bond Second messenger system medicine Nucleotide
Zdroj:	The Journal of Organic Chemistry. 86:15004-15010
ISSN:	1520-6904 0022-3263
Popis:	Cyclic dinucleotides (CDNs) are second messengers composed of two purine nucleotides. In recent years, the structural diversity of CDNs and their functionality in biological processes are being intensely studied. Herein we report the chemical synthesis of cyclic di-5-aminoimidazole-4-carboxamide-1-β-d-ribofuranosyl monophosphate (c-di-ZMP) (1), which consists of two 5-amino-4-imidazolecarboxamide ribonucleotides (Z-ribonucleotides) linked via two phosphodiester linkages. Construction of the CDN skeleton with an N1-dinitrophenylhypoxanthine base (HxaDNP-base) by phosphoramidite chemistry and the subsequent ring-opening reaction of HxaDNP-base successfully yielded the desired 1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8dec2714e90a99d360314767d3efc669 https://doi.org/10.1021/acs.joc.1c01706 Zobrazit plný text záznamu