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117 results on '"Matsuura, Bryan S."'

4. A concise synthesis of tetrodotoxin

Author

Konrad, David B., primary, Rühmann, Klaus-Peter, additional, Ando, Hiroyasu, additional, Hetzler, Belinda E., additional, Strassner, Nina, additional, Houk, Kendall N., additional, Matsuura, Bryan S., additional, and Trauner, Dirk, additional

Published
2022
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6. Perfect and Defective 13C-Furan-Derived Nanothreads from Modest-Pressure Synthesis Analyzed by 13C NMR

Author

Matsuura, Bryan S., primary, Huss, Steven, additional, Zheng, Zhaoxi, additional, Yuan, Shichen, additional, Wang, Tao, additional, Chen, Bo, additional, Badding, John V., additional, Trauner, Dirk, additional, Elacqua, Elizabeth, additional, van Duin, Adri C. T., additional, Crespi, Vincent H., additional, and Schmidt-Rohr, Klaus, additional

Published
2021
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8. Recent Advances in Photoredox Catalysis Enabled Functionalization of alpha-Amino Acids and Peptides : Concepts, Strategies and Mechanisms

Author

Liu, Jian-Quan, Shatskiy, Andrey, Matsuura, Bryan S., Kärkäs, Markus D., Liu, Jian-Quan, Shatskiy, Andrey, Matsuura, Bryan S., and Kärkäs, Markus D.

Abstract

The selective modification of alpha-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues. 1 Introduction 2 Visible-Light-Mediated Functionalization of alpha-Amino Acids 2.1 Decarboxylative Functionalization Involving Redox-Active Esters 2.2 Direct Decarboxylative Coupling Strategies 2.3 Hypervalent Iodine Reagents 2.4 Dual Photoredox and Transition-Metal Catalysis 2.5 Amination and Deamination Strategies 3 Photoinduced Peptide Diversification 3.1 Gese-Type Bioconjugation Methods 3.2 Peptide Macrocyclization through Photoredox Catalysis 3.3 Biomolecule Conjugation through Arylation 3.4 C-H Functionalization Manifolds 4 Conclusions and Outlook, QC 20190920

Published
2019
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11. Sign Inversion in Photopharmacology: Incorporation of Cyclic Azobenzenes in Photoswitchable Potassium Channel Blockers and Openers

Author

Trads, Julie B., primary, Hüll, Katharina, additional, Matsuura, Bryan S., additional, Laprell, Laura, additional, Fehrentz, Timm, additional, Görldt, Nicole, additional, Kozek, Krystian A., additional, Weaver, C. David, additional, Klöcker, Nikolaj, additional, Barber, David M., additional, and Trauner, Dirk, additional

Published
2019
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14. Photocatalytic Oxidation of Lignin Model Systems by Merging Visible-Light Photoredox and Palladium Catalysis

Author

Kärkäs, Markus D., Bosque, Irene, Matsuura, Bryan S., Stephenson, Corey R. J., Kärkäs, Markus D., Bosque, Irene, Matsuura, Bryan S., and Stephenson, Corey R. J.

Abstract

Lignin valorization has long been recognized as a sustainable solution for the renewable production of aromatic compounds. Two-step oxidation/reduction strategies, whereby the first oxidation step is required to “activate” lignin systems for controlled fragmentation reactions, have recently emerged as viable routes toward this goal. Herein we describe a catalytic protocol for oxidation of lignin model systems by combining photoredox and Pd catalysis. The developed dual catalytic protocol allowed the efficient oxidation of lignin model substrates at room temperature to afford the oxidized products in good to excellent yields., QC 20181213

Published
2016
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15. Transition-Metal Catalyzed Valorization of Lignin: The Key to a Sustainable Carbon-Neutral Future

Author

Kärkäs, Markus D., Matsuura, Bryan S., Monos, Timothy M., Magallanes, Gabriel, Stephenson, Corey R. J., Kärkäs, Markus D., Matsuura, Bryan S., Monos, Timothy M., Magallanes, Gabriel, and Stephenson, Corey R. J.

Abstract

The development of a sustainable, carbon-neutral biorefinery has emerged as a prominent scientific and engineering goal of the 21st century. As petroleum has become less accessible, biomass-based carbon sources have been investigated for utility in fuel production and commodity chemical manufacturing. One underutilized biomaterial is lignin; however, its highly crosslinked and randomly polymerized composition have rendered this biopolymer recalcitrant to existing chemical processing. More recently, insight into lignin's molecular structure has reinvigorated chemists to develop catalytic methods for lignin depolymerization. This review examines the development of transition-metal catalyzed reactions and the insights shared between the homogeneous and heterogeneous catalytic systems towards the ultimate goal of valorizing lignin to produce value-added products., QC 20181206

Published
2016
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20. Enchained by Visible Light–Mediated Photoredox Catalysis

Author

Kärkäs, Markus D., Matsuura, Bryan S., Stephenson, Corey R. J., Kärkäs, Markus D., Matsuura, Bryan S., and Stephenson, Corey R. J.

Abstract

Free radicals are exploited in biology, often through highly controlled enzymatic reactions, to drive many reactions that would be difficult via nonradical routes that transfer two electrons (1). In synthetic chemistry, visible-light photoredox catalysis has emerged as an economical and environmentally benign route for promoting free radical transformations in the lab (2–4). Although the initial light-sensitization steps are well established (5), insufficient attention has been dedicated to essential mechanistic features of the closed catalytic cycle (6). Several reports have hypothesized that these photocatalyzed reactions are terminated through a closed catalytic cycle, which delivers the final product and regenerates the ground state of the photosensitizer (PS). However, Cismesia and Yoon (6) highlight that some of the mechanistic proposals may be incomplete and may involve radical chains., QC 20181206

Published
2015
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26. Unravelling Photochemical Relationships Among Natural Products from Aplysia dactylomela

Author

Matsuura, Bryan S., Kölle, Patrick, Trauner, Dirk, de Vivie-Riedle, Regina, and Meier, Robin

Abstract

Aplydactone (1) is a brominated ladderane sesquiterpenoid that was isolated from the sea hare Aplysia dactylomelatogether with the chamigranes dactylone (2) and 10-epi-dactylone (3). Given the habitat of A. dactylomela, it seems likely that 1is formed from 2through a photochemical [2 + 2] cycloaddition. Here, we disclose a concise synthesis of 1, 2, and 3that was guided by excited state theory and relied on several highly stereoselective transformations. Our experiments and calculations confirm the photochemical origin of 1and explain why it is formed as the sole isomer. Irradiation of 3with long wavelength UV light resulted in a [2 + 2] cycloaddition that proceeded with opposite regioselectivity. On the basis of this finding, it seems likely that the resulting regioisomer, termed “8-epi-isoaplydactone”, could also be found in A. dactylomela.

Published
2017
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