Article
Biochemistry & Molecular Biology
Lucia Turell, Martina Steglich, Maria J. Torres, Matias Deambrosi, Laura Antmann, Cristina M. Furdui, Francisco J. Schopfer, Beatriz Alvarez
Summary: This study confirmed the formation process of HSA-SOH and its further oxidation to sulfinic acid and sulfonic acid in the presence of hydrogen peroxide. The decay pathways of HSA-SOH were investigated, revealing its reaction with thiols to form mixed disulfides.
FREE RADICAL BIOLOGY AND MEDICINE
(2021)
Article
Biochemistry & Molecular Biology
Yunlong Shi, Kate S. Carroll
Summary: This study evaluates nucleophilic and electrophilic chemical probes for Cys-SOH, demonstrating that a probe based on the norbornene scaffold does not react with validated sulfenic acid models and that purported cross-reactivity of dimedone-like probes with electrophiles is not meaningful in a biological setting. Nucleophilic probes remain the most viable tools for bioorthogonal detection of Cys-SOH.
Article
Chemistry, Organic
Greg A. Erickson, Mark A. Hatcher, Michel Journet, John A. Kowalski, Tom C. Lovelace, Christopher J. Pink, Shiping Xie
Summary: A novel oxidative activation method was developed to synthesize methyltriazolo [1,4] benzodiazepine in a single step. The method has mild reaction conditions and delivers good yields. It can also be applicable to the synthesis of alkyltriazoles from other thiolactams and acylhydrazines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Plant Sciences
Patrick Willems, Frank Van Breusegem, Jingjing Huang
Summary: Recent advances in proteomic strategies for profiling cysteine redoxome have greatly improved selectivity, in vivo applicability, and quantification, but challenges remain.
Article
Biochemistry & Molecular Biology
Ao Yun Zhang, Chad M. Dashnaw, Mayte Gonzalez, Jordan C. Koone, Nick A. Wells, Colin A. Smith, Matthew J. Guberman-Pfeffer, Bryan F. Shaw
Summary: The oxidation of Cys111 drives the heterodimerization of Cu, Zn superoxide dismutase-1 (SOD1), promoting the pathogenesis of SOD1-linked amyotrophic lateral sclerosis (ALS).
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Ao Yun Zhang, Chad M. Dashnaw, Mayte Gonzalez, Jordan C. Koone, Nick A. Wells, Colin A. Smith, Matthew J. Guberman-Pfeffer, Bryan F. Shaw
Summary: The heterodimerization between wild-type and mutant SOD1 plays a critical role in the development of SOD1-linked ALS. It was found that oxidation of Cys111 can accelerate the rate and increase the free energy of SOD1 heterodimerization. This enhanced heterodimerization is due to electrostatic repulsion between the oxidized and unoxidized forms of SOD1.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Multidisciplinary Sciences
Francesca A. Vaccaro, David A. Born, Catherine L. Drennan
Summary: G-protein metallochaperone MeaB facilitates the delivery of AdoCbl to MCM and genetic defects in MMAA lead to methylmalonic aciduria. The crystal structure of MeaB bound to a GTP analog GMPPCP with the Cbl-binding domain of MeMCMcbl reveals the activation mechanism of MeaB by target protein binding and the rearrangement of switch III region. These results provide insights into the molecular basis of AdoCbl delivery and the role of GTP hydrolysis.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2023)
Article
Chemistry, Multidisciplinary
Benedikt Prasser, Lisa Schoner, Lin Zhang, Oliver Einsle
Summary: The final step of denitrification involves the reduction of nitrous oxide to N-2 by Cu-dependent nitrous oxide reductase (N2OR). The assembly of N2OR is mediated by a metallochaperone encoded by the nos gene cluster, with Cu-A and Cu-Z metal centers. While only Cu-I is delivered to the enzyme, the presence of Zn-II is crucial for the functionality and structural integrity of the chaperone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Spectroscopy
Jessica Renee Knight, Yingying Wang, Shi Xu, Wei Chen, Clifford E. Berkman, Ming Xian
Summary: A unique reaction between thiols and alkyl sulfonylbenzothiazole was discovered, leading to the development of thiol-triggered fluorescent sensors and prodrugs with tunable release profiles of payloads.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2021)
Article
Chemistry, Multidisciplinary
Tsukasa Sano, Ryosuke Masuda, Shohei Sase, Kei Goto
Summary: In this study, an isolable small-molecule cysteine sulfenic acid protected by a molecular cradle was successfully synthesized through direct oxidation of the corresponding cysteine thiol, and its structure was determined by X-ray crystallographic analysis. Biological studies showed its potential as a useful model for studying biorelevant reactivity.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Yongxin Zhang, Helian Li, Xiaoxiao Yang, Pan Zhou, Chao Shu
Summary: The chemistry of cyclic sulfinic acid derivatives has been underdeveloped due to their inaccessibility. However, due to the importance of these derivatives in various scientific fields, synthesis strategies for cyclic sulfinic acid derivatives have gained attention in recent years. This review summarizes the latest advances in the synthesis methods of these derivatives, highlighting product diversity, selectivity, and applicability.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Eileen Bischoff, Lukas Lang, Jannik Zimmermann, Maximilian Luczak, Anna Maria Kiefer, Gereon Niedner-Schatteburg, Georg Manolikakes, Bruce Morgan, Marcel Deponte
Summary: Dimedone and its derivatives are selective probes for nucleophilic detection of sulfenic acids, but they also react with cyclic sulfenamides. Glutathione outcompetes dimedone as a nucleophile by several orders of magnitude. Therefore, the selectivity of dimedone labeling of cysteinyl residues inside living cells is challenged.
FREE RADICAL BIOLOGY AND MEDICINE
(2023)
Article
Multidisciplinary Sciences
Renan B. Ferreira, Ling Fu, Youngeun Jung, Jing Yang, Kate S. Carroll
Summary: The authors have developed a fluorogenic probe for detecting cysteine sulfenic acid, a redox modification closely related to H2O2 signaling and oxidative stress. They also found that kinase inhibitors can modulate the cysteine sulfenome, which has important implications for the field of redox medicine.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Analytical
Jean-Valery Guillaubez, Delphine Pitrat, Yann Bretonniere, Jerome Lemoine, Marion Girod
Summary: Cysteine in proteins is prone to oxidation, and a visible laser-induced dissociation technique was used in a mass spectrometer to streamline the detection of oxidized proteins. By derivatizing cysteine with a chromophore tag, high fragmentation yield was achieved for detecting oxidized peptides. This method has the potential for clinical applications in large human cohorts.
ANALYTICAL CHEMISTRY
(2021)
Review
Chemistry, Organic
Ruwei Bao, Yanping Feng, Danfeng Deng, Dayun Huang, Xiangyu Sun
Summary: The decade advances of sulfinic acids from 2010 to 2021 were summarized in four categories based on mechanisms, including reactions with a variety of compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)