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Short Note

O6-[(2″,3″-O-Isopropylidene-5″-O-tbutyldimethylsilyl)pentyl]-5′-O-tbutyldiphenylsilyl-2′,3′-O-isopropylideneinosine

by 1, 2, 3, 4,5,6, 7 and 2,*
1
Institute of Applied Sciences and Intelligent Systems (ISASI), Unity of Naples, National Research Council (CNR), via Campi Flegrei, 34, 80078 Naples, Italy
2
Department of Pharmacy, University of Naples Federico II, via Domenico Montesano, 49, 80131 Naples, Italy
3
Department of Chemical Sciences, University of Naples Federico II, via Cintia, 21, 80126 Naples, Italy
4
Department of Medical Biochemical Analysis, College of Health Technology, Cihan University—Erbil, Erbil 44001, Kurdistan Region, Iraq
5
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China
6
Guangzhou HC Pharmaceutical Co., Ltd., Guangzhou 510663, China
7
Institute of Experimental Endocrinology and Oncology “Gaetano Salvatore” (IEOS) National Research Council (CNR), via T. De Amicis, 95, 80145 Naples, Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Fawaz Aldabbagh
Molbank 2022, 2022(1), M1345; https://doi.org/10.3390/M1345
Received: 3 February 2022 / Revised: 23 February 2022 / Accepted: 23 February 2022 / Published: 1 March 2022
(This article belongs to the Special Issue Molecules from Side Reactions II)
Cyclic adenosine diphosphate ribose (cADPR) is a cyclic nucleotide involved in the Ca2+ homeostasis. In its structure, the northern ribose, bonded to adenosine through an N1 glycosidic bond, is connected to the southern ribose through a pyrophosphate bridge. Due to the chemical instability at the N1 glycosidic bond, new bioactive cADPR derivatives have been synthesized. One of the most interesting analogues is the cyclic inosine diphosphate ribose (cIDPR), in which the hypoxanthine replaced adenosine. The efforts for synthesizing new linear and cyclic northern ribose modified cIDPR analogues led us to study in detail the inosine N1 alkylation reaction. In the last few years, we have produced new flexible cIDPR analogues, where the northern ribose has been replaced by alkyl chains. With the aim to obtain the closest flexible cIDPR analogue, we have attached to the inosine N1 position a 2″,3″-dihydroxypentyl chain, possessing the two OH groups in a ribose-like fashion. The inosine alkylation reaction afforded also the O6-alkylated regioisomer, which could be a useful intermediate for the construction of new kinds of cADPR mimics. View Full-Text
Keywords: cADPR; nucleosides; nucleotides; inosine; alkylation; calcium mobilization; ryanodine receptor; primary cortical neurons cADPR; nucleosides; nucleotides; inosine; alkylation; calcium mobilization; ryanodine receptor; primary cortical neurons
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MDPI and ACS Style

Marzano, M.; Terracciano, M.; Piccialli, V.; Mahal, A.; Nilo, R.; D’Errico, S. O6-[(2″,3″-O-Isopropylidene-5″-O-tbutyldimethylsilyl)pentyl]-5′-O-tbutyldiphenylsilyl-2′,3′-O-isopropylideneinosine. Molbank 2022, 2022, M1345. https://doi.org/10.3390/M1345

AMA Style

Marzano M, Terracciano M, Piccialli V, Mahal A, Nilo R, D’Errico S. O6-[(2″,3″-O-Isopropylidene-5″-O-tbutyldimethylsilyl)pentyl]-5′-O-tbutyldiphenylsilyl-2′,3′-O-isopropylideneinosine. Molbank. 2022; 2022(1):M1345. https://doi.org/10.3390/M1345

Chicago/Turabian Style

Marzano, Maria, Monica Terracciano, Vincenzo Piccialli, Ahmed Mahal, Roberto Nilo, and Stefano D’Errico. 2022. "O6-[(2″,3″-O-Isopropylidene-5″-O-tbutyldimethylsilyl)pentyl]-5′-O-tbutyldiphenylsilyl-2′,3′-O-isopropylideneinosine" Molbank 2022, no. 1: M1345. https://doi.org/10.3390/M1345

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