{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Andy D"],"funding":["Medical College of Wisconsin","National Institutes of Health","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["117099"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9842072"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["76"],"pubmed_abstract":["A photo-clickable analog of adenosine was devised and synthesized in which the photoactive functional group (8-azidoadenosine) and the click moiety (2'-O-propargyl-ether) were compactly combined within the structure of the adenosine nucleoside itself. We synthesized 8-N<sub>3</sub>-2'-O-propargyl adenosine in four steps starting from adenosine. This photo-clickable adenosine was 5'-phosphorylated and coupled to nicotinamide mononucleotide to form the NAD analog 8-N<sub>3</sub>-2'-O-propargyl-NAD. This NAD analog was recognized by Aplysia californica ADP-ribosyl cyclase and enzymatically cyclized producing 8-N<sub>3</sub>-2'-O-propargyl cyclic ADP-ribose. Photo-clickable cyclic-ADP-ribose analog was envisioned as a probe to label cyclic ADP-ribose binding proteins. The monofunctional 8-N<su"],"journal":["Bioorganic & medicinal chemistry"],"pubmed_title":["Synthesis and biological evaluation of novel photo-clickable adenosine and cyclic ADP-ribose analogs: 8-N<sub>3</sub>-2'-O-propargyladenosine and 8-N<sub>3</sub>-2'-O-propargyl-cADPR."],"pmcid":["PMC9842072"],"funding_grant_id":["R01 GM088790","R01-GM088790","R15-GM131329","R15 GM131329"],"pubmed_authors":["Walseth TF","Gunaratne GS","Marchant JS","Slama JT","Andy D"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis and biological evaluation of novel photo-clickable adenosine and cyclic ADP-ribose analogs: 8-N<sub>3</sub>-2'-O-propargyladenosine and 8-N<sub>3</sub>-2'-O-propargyl-cADPR.","description":"A photo-clickable analog of adenosine was devised and synthesized in which the photoactive functional group (8-azidoadenosine) and the click moiety (2'-O-propargyl-ether) were compactly combined within the structure of the adenosine nucleoside itself. We synthesized 8-N<sub>3</sub>-2'-O-propargyl adenosine in four steps starting from adenosine. This photo-clickable adenosine was 5'-phosphorylated and coupled to nicotinamide mononucleotide to form the NAD analog 8-N<sub>3</sub>-2'-O-propargyl-NAD. This NAD analog was recognized by Aplysia californica ADP-ribosyl cyclase and enzymatically cyclized producing 8-N<sub>3</sub>-2'-O-propargyl cyclic ADP-ribose. Photo-clickable cyclic-ADP-ribose analog was envisioned as a probe to label cyclic ADP-ribose binding proteins. The monofunctional 8-N<su","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Dec","modification":"2025-04-04T03:01:16.662Z","creation":"2025-04-04T03:01:16.662Z"},"accession":"S-EPMC9842072","cross_references":{"pubmed":["36446271"],"doi":["10.1016/j.bmc.2022.117099"]}}