{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Wojtczak BA"],"funding":["Fundacja na rzecz Nauki Polskiej","Narodowe Centrum Nauki","European Regional Development Fund"],"pagination":["6827-6846"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10242767"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["88(11)"],"pubmed_abstract":["Chemical modifications of the mRNA cap structure can enhance the stability, translational properties, and half-life of mRNAs, thereby altering the therapeutic properties of synthetic mRNA. However, cap structure modification is challenging because of the instability of the 5'-5'-triphosphate bridge and N7-methylguanosine. The Suzuki-Miyaura cross-coupling reaction between boronic acid and halogen compound is a mild, convenient, and potentially applicable approach for modifying biomolecules. Herein, we describe two methods to synthesize C8-modified cap structures using the Suzuki-Miyaura cross-coupling reaction. Both methods employed phosphorimidazolide chemistry to form the 5',5'-triphosphate bridge. However, in the first method, the introduction of the modification <i>via</i> the Suzuki-M"],"journal":["The Journal of organic chemistry"],"pubmed_title":["Synthesis and Evaluation of Diguanosine Cap Analogs Modified at the C8-Position by Suzuki-Miyaura Cross-Coupling: Discovery of 7-Methylguanosine-Based Molecular Rotors."],"pmcid":["PMC10242767"],"funding_grant_id":["POIR.04.04.00-00-20A2/16","UMO-2016/21/N/ST4/03750","POIR.04.04.00-00- 20A2/16","UMO-2017/26/D/ST5/00901"],"pubmed_authors":["Surynt P","Wojtczak A","Bednarczyk M","Wojtczak BA","Sikorski PJ","Jemielity J","Kowalska J"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis and Evaluation of Diguanosine Cap Analogs Modified at the C8-Position by Suzuki-Miyaura Cross-Coupling: Discovery of 7-Methylguanosine-Based Molecular Rotors.","description":"Chemical modifications of the mRNA cap structure can enhance the stability, translational properties, and half-life of mRNAs, thereby altering the therapeutic properties of synthetic mRNA. However, cap structure modification is challenging because of the instability of the 5'-5'-triphosphate bridge and N7-methylguanosine. The Suzuki-Miyaura cross-coupling reaction between boronic acid and halogen compound is a mild, convenient, and potentially applicable approach for modifying biomolecules. Herein, we describe two methods to synthesize C8-modified cap structures using the Suzuki-Miyaura cross-coupling reaction. Both methods employed phosphorimidazolide chemistry to form the 5',5'-triphosphate bridge. However, in the first method, the introduction of the modification <i>via</i> the Suzuki-M","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Jun","modification":"2025-05-29T20:24:16.239Z","creation":"2025-05-29T20:24:16.239Z"},"accession":"S-EPMC10242767","cross_references":{"pubmed":["37209102"],"doi":["10.1021/acs.joc.3c00126"]}}