Synthesis of a Cyclic Dinucleotide Analogue with Ambiguous Bases, 5-Aminoimidazole-4-carboxamide
Autor: | Yoshiyuki Tanaka, Noriaki Minakawa, Noriko Tarashima, Yusuke Kumanomido, Katsuyuki Nakashima |
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Rok vydání: | 2021 |
Předmět: | |
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 |
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