The Experts below are selected from a list of 801 Experts worldwide ranked by ideXlab platform
Kate S. Carroll - One of the best experts on this subject based on the ideXlab platform.
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proteome wide analysis of cysteine s sulfenylation using a benzothiazine based probe
Current protocols in protein science, 2019Co-Authors: Keke Liu, Kate S. Carroll, Renan B Ferreira, Jing YangAbstract:Oxidation of a protein cysteinyl thiol (Cys-SH) to S-sulfenic acid (Cys-SOH) by a reactive oxygen species (e.g., hydrogen peroxide), which is termed protein S-sulfenylation, is a reversible post-translational modification that plays a crucial role in redox regulation of protein function in various biological processes. Due to its intrinsically labile nature, protein S-sulfenylation cannot be directly detected or analyzed. Chemoselective probing has been the method of choice for analyzing S-sulfenylated proteins either in vitro or in situ, as it allows stabilization and direct detection of this transient oxidative intermediate. However, it remains challenging to globally pinpoint the specific S-sulfenylated cysteine sites on complex proteomes and to quantify their dynamic changes upon oxidative stress. This unit describes how a benzothiazine-based chemoselective probe called BTD and mass spectrometry based chemoproteomics can be used to globally and site-specifically identify and quantify protein S-sulfenylation. © 2018 by John Wiley & Sons, Inc.
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Chemical proteomics reveals new targets of cysteine sulfinic acid reductase.
Nature chemical biology, 2018Co-Authors: Salma Akter, Youngeun Jung, Mauro Lo Conte, J. Reed Lawson, W. Todd Lowther, Rui Sun, Keke Liu, Jing Yang, Kate S. CarrollAbstract:Cysteine sulfinic acid or S-sulfinylation is an oxidative post-translational modification (OxiPTM) that is known to be involved in redox-dependent regulation of protein function but has been historically difficult to analyze biochemically. To facilitate the detection of S-sulfinylated proteins, we demonstrate that a clickable, electrophilic diazene probe (DiaAlk) enables capture and site-centric proteomic analysis of this OxiPTM. Using this workflow, we revealed a striking difference between sulfenic acid modification (S-sulfenylation) and the S-sulfinylation dynamic response to oxidative stress, which is indicative of different roles for these OxiPTMs in redox regulation. We also identified >55 heretofore-unknown protein substrates of the cysteine sulfinic acid reductase sulfiredoxin, extending its function well beyond those of 2-cysteine peroxiredoxins (2-Cys PRDX1-4) and offering new insights into the role of this unique oxidoreductase as a central mediator of reactive oxygen species-associated diseases, particularly cancer. DiaAlk therefore provides a novel tool to profile S-sulfinylated proteins and study their regulatory mechanisms in cells.
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the redox biochemistry of protein sulfenylation and sulfinylation
Journal of Biological Chemistry, 2013Co-Authors: Mauro Lo Conte, Kate S. CarrollAbstract:Controlled generation of reactive oxygen species orchestrates numerous physiological signaling events (Finkel, T. (2011) Signal transduction by reactive oxygen species. J. Cell Biol. 194, 7–15). A major cellular target of reactive oxygen species is the thiol side chain (RSH) of Cys, which may assume a wide range of oxidation states (i.e. −2 to +4). Within this context, Cys sulfenic (Cys-SOH) and sulfinic (Cys-SO2H) acids have emerged as important mechanisms for regulation of protein function. Although this area has been under investigation for over a decade, the scope and biological role of sulfenic/sulfinic acid modifications have been recently expanded with the introduction of new tools for monitoring cysteine oxidation in vitro and directly in cells. This minireview discusses selected recent examples of protein sulfenylation and sulfinylation from the literature, highlighting the role of these post-translational modifications in cell signaling.
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peroxide dependent sulfenylation of the egfr catalytic site enhances kinase activity
Nature Chemical Biology, 2012Co-Authors: Candice E Paulsen, Thu H Truong, Francisco J Garcia, Arne Homann, Vinayak Gupta, Stephen E Leonard, Kate S. CarrollAbstract:A sensitive probe that detects protein sulfenylation in cells reveals that sulfenylation of the active site cysteine in EGFR enhances its kinase activity.
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peroxide dependent sulfenylation of the egfr catalytic site enhances kinase activity
Nature Chemical Biology, 2012Co-Authors: Candice E Paulsen, Thu H Truong, Francisco J Garcia, Arne Homann, Vinayak Gupta, Stephen E Leonard, Kate S. CarrollAbstract:A sensitive probe that detects protein sulfenylation in cells reveals that sulfenylation of the active site cysteine in EGFR enhances its kinase activity. Protein sulfenylation is a post-translational modification of emerging importance in higher eukaryotes. However, investigation of its diverse roles remains challenging, particularly within a native cellular environment. Herein we report the development and application of DYn-2, a new chemoselective probe for detecting sulfenylated proteins in human cells. These studies show that epidermal growth factor receptor–mediated signaling results in H2O2 production and oxidation of downstream proteins. In addition, we demonstrate that DYn-2 has the ability to detect differences in sulfenylation rates within the cell, which are associated with differences in target protein localization. We also show that the direct modification of epidermal growth factor receptor by H2O2 at a critical active site cysteine (Cys797) enhances its tyrosine kinase activity. Collectively, our findings reveal sulfenylation as a global signaling mechanism that is akin to phosphorylation and has regulatory implications for other receptor tyrosine kinases and irreversible inhibitors that target oxidant-sensitive cysteines in proteins.
Kewen Tang - One of the best experts on this subject based on the ideXlab platform.
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silver mediated oxidative c c bond Sulfonylation arylation of methylenecyclopropanes with sodium sulfinates facile access to 3 sulfonyl 1 2 dihydronaphthalenes
Organic and Biomolecular Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Changan Yang, Kewen TangAbstract:The novel AgNO3-mediated oxidative Sulfonylation/arylation of a C–C σ-bond in methylenecyclopropanes with sodium sulfinates to synthesize various 3-sulfonylated 1,2-dihydronaphthalenes is reported. This Sulfonylation/arylation transformation proceeds via a sequence of Sulfonylation, C–C σ-bond cleavage and intramolecular cyclization, and the experimental results show that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for the difunctionalization of C–C bonds with a phenyl ring and a sulfonyl radical via the one-pot construction of a C–S bond and a new C–C bond.
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visible light catalyzed c c bond difunctionalization of methylenecyclopropanes with sulfonyl chlorides for the synthesis of 3 sulfonyl 1 2 dihydronaphthalenes
Journal of Organic Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of C═C bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond.
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Visible-Light-Catalyzed C–C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3‑Sulfonyl-1,2-dihydronaphthalenes
2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond
Yu Liu - One of the best experts on this subject based on the ideXlab platform.
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silver mediated oxidative c c bond Sulfonylation arylation of methylenecyclopropanes with sodium sulfinates facile access to 3 sulfonyl 1 2 dihydronaphthalenes
Organic and Biomolecular Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Changan Yang, Kewen TangAbstract:The novel AgNO3-mediated oxidative Sulfonylation/arylation of a C–C σ-bond in methylenecyclopropanes with sodium sulfinates to synthesize various 3-sulfonylated 1,2-dihydronaphthalenes is reported. This Sulfonylation/arylation transformation proceeds via a sequence of Sulfonylation, C–C σ-bond cleavage and intramolecular cyclization, and the experimental results show that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for the difunctionalization of C–C bonds with a phenyl ring and a sulfonyl radical via the one-pot construction of a C–S bond and a new C–C bond.
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visible light catalyzed c c bond difunctionalization of methylenecyclopropanes with sulfonyl chlorides for the synthesis of 3 sulfonyl 1 2 dihydronaphthalenes
Journal of Organic Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of C═C bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond.
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Visible-Light-Catalyzed C–C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3‑Sulfonyl-1,2-dihydronaphthalenes
2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond
Mohan M Bhadbhade - One of the best experts on this subject based on the ideXlab platform.
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Sulfonate protecting groups. Regioselective Sulfonylation of myo-inositol orthoesters-improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Carbohydrate Research, 2002Co-Authors: Kana M. Sureshan, Thoniyot Praveen, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M BhadbhadeAbstract:Abstract The regioselectivity of Sulfonylation of myo-inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. MonoSulfonylation of myo-inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the Sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in Sulfonylation of the 2-hydroxyl group. DiSulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of myo-inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding myo-inositol orthoester derivative. These new methods of protection–deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-myo-inositol, which are precursors for the synthesis of d - and l -myo-inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-myo-inositol which is a precursor for the preparation of myo-inositol 1,3,4,5,6-pentakisphosphate.
Qiaolin Wang - One of the best experts on this subject based on the ideXlab platform.
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silver mediated oxidative c c bond Sulfonylation arylation of methylenecyclopropanes with sodium sulfinates facile access to 3 sulfonyl 1 2 dihydronaphthalenes
Organic and Biomolecular Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Changan Yang, Kewen TangAbstract:The novel AgNO3-mediated oxidative Sulfonylation/arylation of a C–C σ-bond in methylenecyclopropanes with sodium sulfinates to synthesize various 3-sulfonylated 1,2-dihydronaphthalenes is reported. This Sulfonylation/arylation transformation proceeds via a sequence of Sulfonylation, C–C σ-bond cleavage and intramolecular cyclization, and the experimental results show that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for the difunctionalization of C–C bonds with a phenyl ring and a sulfonyl radical via the one-pot construction of a C–S bond and a new C–C bond.
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visible light catalyzed c c bond difunctionalization of methylenecyclopropanes with sulfonyl chlorides for the synthesis of 3 sulfonyl 1 2 dihydronaphthalenes
Journal of Organic Chemistry, 2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of C═C bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond.
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Visible-Light-Catalyzed C–C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3‑Sulfonyl-1,2-dihydronaphthalenes
2019Co-Authors: Yu Liu, Qiaolin Wang, Zan Chen, Quan Zhou, Congshan Zhou, Biquan Xiong, Panliang Zhang, Kewen TangAbstract:A novel visible-light-catalyzed Sulfonylation/arylation of carbon–carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of CC bond Sulfonylation, C–C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C–C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C–C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C–S bond and a new C–C bond
