Application of (aza)quinolizinyl-3-diazonium tetrafluoroborates in photocatalytic sulfanylation and in fluorescent labeling of proteins

Jurajevčič, Manca (author), Grošelj, Lena (author), Ciber, Luka (author), Grošelj, Uroš (author), Van Midden, Katarina Petra (author), Petek, Nejc (author), Štefane, Bogdan (author), Novinec, Marko (author), Svete, Jurij (author)

Photocatalytic sulfanylations of (aza)quinolizine diazonium salts with disulfides and thiols, including N-Boc-protected cysteine and cystine esters, gave the corresponding fluorescent sulfanylation products in 25–85 % yield. Photocatalytic cycle was proposed for the sulfanylation with disulfides using diazonium salts as heteroaryl radical sources. Two representative diazonium salts were evaluated as bioconjugation reagents for fluorescent labeling of proteins using bovine serum albumin (BSA) as a model protein and targeting cysteine residues, and the results showed their applicability in fluorescent labeling under photocatalytic conditions.

• Language: English
• Keywords: sulfanylation, arylation, quinolizines, azaquinolizines, photoredox catalysis, diazonium salts, bioconjugation, fluorescent labeling, proteins
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2025
• Number of pages: 17 str.
• Numbering: Vol. 163, art. 108686
• PID: 20.500.12556/RUL-169988
• UDC: 547.83:544.526.5:577.112
• ISSN on article: 0045-2068
• DOI: 10.1016/j.bioorg.2025.108686
• COBISS.SI-ID: 240849155
• Publication date in RUL: 01.07.2025

Record is a part of a journal

• Title: Bioorganic chemistry
• Shortened title: Bioorg. chem.
• Publisher: Academic Press
• ISSN: 0045-2068
• COBISS.SI-ID: 25099008

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: sulfaniliranje, ariliranje, kinolizini, azakinolizini, fotoredoks kataliza, diazonijeve soli, biokonjugacija, fluorescentno označevanje, proteini

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: N1-0211
• Name: Uvedba kooperativnosti v peptidaze za izboljšanje njihove aktivnosti in uravnavanja