Visible-Light-Mediated Modification and Manipulation of Biomacromolecules DOI

Vivian M. Lechner,

Manuel Nappi, Patrick J. Deneny

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1752 - 1829

Published: Sept. 21, 2021

Chemically modified biomacromolecules─i.e., proteins, nucleic acids, glycans, and lipids─have become crucial tools in chemical biology. They are extensively used not only to elucidate cellular processes but also industrial applications, particularly the context of biopharmaceuticals. In order enable maximum scope for optimization, it is pivotal have a diverse array biomacromolecule modification methods at one's disposal. Chemistry has driven many significant advances this area, especially recently, numerous novel visible-light-induced photochemical approaches emerged. these reactions, light serves as an external source energy, enabling access highly reactive intermediates under exceedingly mild conditions with exquisite spatiotemporal control. While UV-induced transformations on biomacromolecules date back decades, visible unmistakable advantage being considerably more biocompatible, spectrum visible-light-driven now available, chiefly proteins acids. This review will discuss modifications native functional groups (FGs), including functionalization, labeling, cross-linking techniques well utility oxidative degradation mediated by photochemically generated oxygen species. Furthermore, non-native, bioorthogonal FGs be addressed, photoclick chemistry DNA-encoded library synthesis that allow manipulation activity biomacromolecule.

Language: Английский

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry DOI
Laura Buglioni, Fabian Raymenants, Aidan Slattery

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2752 - 2906

Published: Aug. 10, 2021

Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing plethora opportunities to synthetic organic chemists. However, performing photochemical transformation can be quite challenge because various issues related the delivery photons. These challenges barred widespread adoption steps industry. past decade, several technological innovations led more reproducible, selective, and scalable photoinduced reactions. Herein, we provide comprehensive overview these exciting advances, including flow chemistry, high-throughput experimentation, reactor design scale-up, combination photo- electro-chemistry.

Language: Английский

Citations

544
Graphitic carbon nitride-based photocatalysts: Toward efficient organic transformation for value-added chemicals production DOI
Anise Akhundi, Alireza Badiei, Ghodsi Mohammadi Ziarani

et al.

Molecular Catalysis, Journal Year: 2020, Volume and Issue: 488, P. 110902 - 110902

Published: April 11, 2020

Language: Английский

Citations

482
Triplet Energy Transfer Photocatalysis: Unlocking the Next Level DOI Creative Commons
Felix Strieth‐Kalthoff, Frank Glorius

Chem, Journal Year: 2020, Volume and Issue: 6(8), P. 1888 - 1903

Published: Aug. 1, 2020

Language: Английский

Citations

444
Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents DOI Creative Commons
Jonathan D. Bell, John A. Murphy

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(17), P. 9540 - 9685

Published: Jan. 1, 2021

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

Language: Английский

Citations

345
Enantioselective Photochemical Reactions Enabled by Triplet Energy Transfer DOI
Johannes Großkopf,

Thilo Kratz,

Thomas Rigotti

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1626 - 1653

Published: July 6, 2021

For molecules with a singlet ground state, the population of triplet states is mainly possible (a) by direct excitation and subsequent intersystem crossing or (b) energy transfer from an appropriate sensitizer. The latter scenario enables catalytic photochemical reaction in which sensitizer adopts role catalyst undergoing several cycles photon absorption to substrate. If product molecule triplet-sensitized process chiral, this can proceed enantioselectively upon judicious choice chiral An enantioselective also occur dual approach which, apart achiral sensitizer, second activates substrate toward sensitization. Although idea reactions via intermediates has been pursued for more than 50 years, notable selectivities exceeding 90% enantiomeric excess (ee) have only realized past decade. This review attempts provide comprehensive survey on various were rendered

Language: Английский

Citations

341
Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds DOI
Rolando Cannalire, Sveva Pelliccia, Luca Sancineto

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(2), P. 766 - 897

Published: Dec. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Language: Английский

Citations

336
Photocatalytic Late-Stage C–H Functionalization DOI
Peter Bellotti, Huan‐Ming Huang,

Teresa Faber

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(8), P. 4237 - 4352

Published: Jan. 24, 2023

The emergence of modern photocatalysis, characterized by mildness and selectivity, has significantly spurred innovative late-stage C–H functionalization approaches that make use low energy photons as a controllable source. Compared to traditional strategies, photocatalysis paves the way toward complementary and/or previously unattainable regio- chemoselectivities. Merging compelling benefits with workflow offers potentially unmatched arsenal tackle drug development campaigns beyond. This Review highlights photocatalytic strategies small-molecule drugs, agrochemicals, natural products, classified according targeted bond newly formed one. Emphasis is devoted identifying, describing, comparing main mechanistic scenarios. draws critical comparison between established ionic chemistry photocatalyzed radical-based manifolds. aims establish current state-of-the-art illustrate key unsolved challenges be addressed in future. authors aim introduce general readership functionalization, specialist practitioners evaluation methodologies, potential for improvement, future uncharted directions.

Language: Английский

Citations

336
Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts DOI
Tomáš Neveselý,

Max Wienhold,

John J. Molloy

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2650 - 2694

Published: Aug. 27, 2021

Geometrical E → Z alkene isomerization is intimately entwined in the historical fabric of organic photochemistry and enjoying a renaissance (Roth et al. Angew. Chem., Int. Ed. Engl. 1989 28, 1193–1207). This consequence fundamental stereochemical importance Z-alkenes, juxtaposed with frustrations thermal reactivity that are rooted microscopic reversibility. Accessing excited state paradigms allow this latter obstacle to be circumnavigated by exploiting subtle differences photophysical behavior substrate product chromophores: provides molecular basis for directionality. While direct irradiation operationally simple, photosensitization via selective energy transfer enables augmentation repertoire include substrates not directly photons. Through sustained innovation, an impressive portfolio tailored small molecule catalysts range triplet energies now widely available facilitate contra-thermodynamic thermo-neutral reactions generate Z-alkene fragments. review intended serve as practical guide covering geometric alkenes enabled catalysis from 2000 2020, logical sequel excellent treatment Dugave Demange (Chem. Rev. 2003 103, 2475–2532). The mechanistic foundations underpinning selectivity discussed together induction models rationales explain counterintuitive directionality these processes which very distinguish product. Implications subsequent stereospecific transformations, application total synthesis, regioselective polyene isomerization, spatiotemporal control pre-existing configuration broader sense discussed.

Language: Английский

Citations

321
Advances in Catalytic Asymmetric Dearomatization DOI Creative Commons
Chao Zheng, Shu‐Li You

ACS Central Science, Journal Year: 2021, Volume and Issue: 7(3), P. 432 - 444

Published: Feb. 22, 2021

Asymmetric catalysis has been recognized as the most enabling strategy for accessing chiral molecules in enantioenriched forms. Catalytic asymmetric dearomatization is an emerging and dynamic research subject catalysis, which received considerable attention recent years. The direct transformations from readily available aromatic feedstocks to structurally diverse three-dimensional polycyclic make catalytic reactions of broad interest both organic synthesis medicinal chemistry. However, inherent difficulty disruption aromaticity demands a large energy input during process, might be incompatible with conditions generally required by catalysis. In this Outlook, we will discuss representative strategies examples various compounds try convince readers that overcoming above obstacles, could advance chemical sciences many respects.

Language: Английский

Citations

309
Hantzsch esters: an emerging versatile class of reagents in photoredox catalyzed organic synthesis DOI

Peng‐Zi Wang,

Jia‐Rong Chen, Wen‐Jing Xiao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(29), P. 6936 - 6951

Published: Jan. 1, 2019

This minireview highlights the recent advances in chemistry of Hantzsch esters photoredox catalyzed organic synthesis, with particular emphasis placed on reaction mechanisms.

Language: Английский

Citations

294