Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF4 )-Derived Connective Hubs for Bioconjugation to DNA and Proteins

Angewandte Chemie
Feng LiuK Barry Sharpless

Abstract

We report here the development of a suite of biocompatible SuFEx transformations from the SOF4 -derived iminosulfur oxydifluoride hub in aqueous buffer conditions. These biocompatible SuFEx reactions of iminosulfur oxydifluorides (R-N=SOF2 ) with primary amines give sulfamides (8 examples, up to 98 %), while the reaction with secondary amines furnish sulfuramidimidoyl fluoride products (8 examples, up to 97 %). Likewise, under mild buffered conditions, phenols react with the iminosulfur oxydifluorides (Ar-N=SOF2 ) to produce sulfurofluoridoimidates (13 examples, up to 99 %), which can themselves be further modified by nucleophiles. These transformations open the potential for asymmetric and trisubstituted linkages projecting from the sulfur(VI) center, including versatile S-N and S-O connectivity (9 examples, up to 94 %). Finally, the SuFEx bioconjugation of iminosulfur oxydifluorides to amine-tagged single-stranded DNA and to BSA protein demonstrate the potential of SOF4 -derived SuFEx click chemistry in biological applications.

References

Jun 15, 1992·Proceedings of the National Academy of Sciences of the United States of America·S Brenner, R A Lerner
Oct 19, 2007·Proceedings of the National Academy of Sciences of the United States of America·Jeremy M BaskinCarolyn R Bertozzi
Feb 10, 2009·Proceedings of the National Academy of Sciences of the United States of America·Peng WuCarolyn R Bertozzi
Aug 29, 2009·Angewandte Chemie·Ellen M Sletten, Carolyn R Bertozzi
Nov 11, 2010·Journal of the American Chemical Society·David Soriano Del AmoPeng Wu
Mar 8, 2012·Journal of the American Chemical Society·Giulio CasiDario Neri
Aug 8, 2014·Angewandte Chemie·Jiajia DongValery V Fokin
Aug 13, 2014·Angewandte Chemie·Jiajia DongK Barry Sharpless
Mar 31, 2015·Nature Chemical Biology·James I MacDonaldMatthew B Francis
Jun 9, 2015·Journal of the American Chemical Society·Aleksandra BaranczakJeffery W Kelly
Jan 23, 2016·Nature Chemistry·Chi ZhangBradley L Pentelute
Mar 15, 2016·ACS Combinatorial Science·Marie Lynne Malone, Brian M Paegel
Mar 19, 2016·Chemistry : a European Journal·Enxuan ZhangK Barry Sharpless
Mar 22, 2016·Chemical Communications : Chem Comm·Christian Hoppmann, Lei Wang
Nov 3, 2016·Chemistry : a European Journal·Jeremy YatvinJason Locklin
Nov 5, 2016·The Journal of Organic Chemistry·Qinheng ZhengK Barry Sharpless
Jan 12, 2017·Organic Letters·Praveen K ChinthakindiPer I Arvidsson
Jan 18, 2017·Angewandte Chemie·Richard A Lerner, Sydney Brenner
Jan 25, 2017·Organic & Biomolecular Chemistry·Alessandro Dondoni, Alberto Marra
Mar 24, 2017·Organic Letters·Gerui RenHua Wang
Apr 4, 2017·Angewandte Chemie·Gao-Feng ZhaK Barry Sharpless
Apr 24, 2018·FEBS Letters·Nicholas FavalliDario Neri
Jun 24, 2018·Chemistry : a European Journal·Eun Joung ChoiB Moon Kim

❮ Previous
Next ❯

Citations

Aug 1, 2019·Chemical Society Reviews·A S BarrowJ E Moses
Apr 14, 2020·Angewandte Chemie·Hongtao XuRichard A Lerner
May 20, 2020·Chemistry : a European Journal·Stephanie GreedJames Adam Bull
Oct 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jonathan HiraChristian S Lentz
Apr 3, 2021·Journal of Medicinal Chemistry·Luca GambiniMaurizio Pellecchia
May 7, 2021·Chemical Communications : Chem Comm·Yiyuan ZhangHongtao Xu
Jun 4, 2021·ACS Central Science·Leopold Garnar-WortzelMichael A Erb
Jun 8, 2021·Chemical Science·Ryan W KulowQuentin Michaudel
Jun 8, 2021·Chemical Science·Zhoulong FanJin-Quan Yu
Jul 11, 2021·Proceedings of the National Academy of Sciences of the United States of America·Jiong ZhangK Barry Sharpless
Aug 26, 2020·Journal of the American Chemical Society·Thomas Q DaviesMichael C Willis
Aug 14, 2020·ACS Combinatorial Science·Alexander K Price, Brian M Paegel
Jul 15, 2021·Angewandte Chemie·Shoujun SunJiajia Dong
Nov 2, 2019·The Journal of Organic Chemistry·Shuning ZhangGuang Yang
Jun 2, 2020·Journal of the American Chemical Society·Seiya KitamuraDennis W Wolan
Sep 4, 2021·Bioorganic & Medicinal Chemistry Letters·Richard J FairChristopher D Hupp

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.