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  1. Article ; Online: Improved Synthesis of a Cyclic Glutamine Analogue Used in Antiviral Agents Targeting 3C and 3CL Proteases Including SARS-CoV-2 M

    Vuong, Wayne / Vederas, John C

    The Journal of organic chemistry

    2021  Volume 86, Issue 18, Page(s) 13104–13110

    Abstract: An intermediate in the synthesis of numerous antiviral protease inhibitors is the glutamine analogue, ( ... ...

    Abstract An intermediate in the synthesis of numerous antiviral protease inhibitors is the glutamine analogue, (3
    MeSH term(s) Antiviral Agents/pharmacology ; COVID-19 ; Coronavirus 3C Proteases/antagonists & inhibitors ; Glutamine ; Humans ; Protease Inhibitors/pharmacology ; SARS-CoV-2/drug effects ; SARS-CoV-2/enzymology
    Chemical Substances Antiviral Agents ; Protease Inhibitors ; Glutamine (0RH81L854J) ; 3C-like protease, SARS coronavirus (EC 3.4.22.-) ; Coronavirus 3C Proteases (EC 3.4.22.28)
    Language English
    Publishing date 2021-08-28
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c01299
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
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    Jg. 1995 - 2021: Lesesall (2.OG)
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  2. Article: Improved Synthesis of a Cyclic Glutamine Analogue Used in Antiviral Agents Targeting 3C and 3CL Proteases Including SARS-CoV-2 Mᵖʳᵒ

    Vuong, Wayne / Vederas, John C.

    Journal of organic chemistry. 2021 Aug. 28, v. 86, no. 18

    2021  

    Abstract: An intermediate in the synthesis of numerous antiviral protease inhibitors is the glutamine analogue, (3S)-pyrrolid-2-one-3-yl-l-alanine. Preparations of compounds based on this pharmacophore are hindered by the lack of a reliably high yielding synthesis ...

    Abstract An intermediate in the synthesis of numerous antiviral protease inhibitors is the glutamine analogue, (3S)-pyrrolid-2-one-3-yl-l-alanine. Preparations of compounds based on this pharmacophore are hindered by the lack of a reliably high yielding synthesis of protected forms of this amino acid. We describe an improved scalable route with readily available reagents and facile purification. This methodology employs γ-allylation of dimethyl N-BocGlu, further Boc N-protection, OsO₄-periodate oxidation, O-Me oxime formation, and RaNi-catalyzed hydrogenolysis with concomitant cyclization under basic conditions.
    Keywords Severe acute respiratory syndrome coronavirus 2 ; glutamine ; organic chemistry ; oxidation ; pharmacology ; proteinases
    Language English
    Dates of publication 2021-0828
    Size p. 13104-13110.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c01299
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  3. Article ; Online: Deuteration for Metabolic Stabilization of SARS-CoV-2 Inhibitors GC373 and Nirmatrelvir.

    Van Oers, Tayla J / Piercey, Alexia / Belovodskiy, Alexandr / Reiz, Béla / Donnelly, Bethan L / Vuong, Wayne / Lemieux, M Joanne / Nieman, James A / Auclair, Karine / Vederas, John C

    Organic letters

    2023  Volume 25, Issue 31, Page(s) 5885–5889

    Abstract: Nirmatrelvir and GC373 inhibit the SARS-CoV-2 3CL protease and hinder viral replication in COVID-19. As nirmatrelvir in Paxlovid is oxidized by cytochrome P450 3A4, ritonavir is coadministered to block this. However, ritonavir undesirably alters the ... ...

    Abstract Nirmatrelvir and GC373 inhibit the SARS-CoV-2 3CL protease and hinder viral replication in COVID-19. As nirmatrelvir in Paxlovid is oxidized by cytochrome P450 3A4, ritonavir is coadministered to block this. However, ritonavir undesirably alters the metabolism of other drugs. Hydrogens can be replaced with deuterium in nirmatrelvir and GC373 to slow oxidation. Results show that deuterium slows oxidation of nirmatrelvir adjacent to nitrogen by ∼40% and that the type of warhead can switch the site of oxidative metabolism.
    MeSH term(s) Humans ; Ritonavir/pharmacology ; SARS-CoV-2 ; Deuterium ; COVID-19 ; Antiviral Agents/pharmacology
    Chemical Substances nirmatrelvir and ritonavir drug combination ; Ritonavir (O3J8G9O825) ; phenylmethyl N-((1S)-1-((((1S)-1-formyl-2-(2-oxo-3-pyrrolidinyl)ethyl)amino)carbonyl)-3-methylbutyl)carbamate (W9SVW656LQ) ; Deuterium (AR09D82C7G) ; Antiviral Agents
    Language English
    Publishing date 2023-07-31
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c02140
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Crystallization of Feline Coronavirus M

    Lu, Jimmy / Chen, Sizhu Amelia / Khan, Muhammad Bashir / Brassard, Raelynn / Arutyunova, Elena / Lamer, Tess / Vuong, Wayne / Fischer, Conrad / Young, Howard S / Vederas, John C / Lemieux, M Joanne

    Frontiers in chemistry

    2022  Volume 10, Page(s) 852210

    Abstract: Coronaviruses infect a variety of hosts in the animal kingdom, and while each virus is taxonomically different, they all infect their ... ...

    Abstract Coronaviruses infect a variety of hosts in the animal kingdom, and while each virus is taxonomically different, they all infect their host
    Language English
    Publishing date 2022-02-24
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2711776-5
    ISSN 2296-2646
    ISSN 2296-2646
    DOI 10.3389/fchem.2022.852210
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: N-Terminal Finger Stabilizes the S1 Pocket for the Reversible Feline Drug GC376 in the SARS-CoV-2 M

    Arutyunova, Elena / Khan, Muhammad Bashir / Fischer, Conrad / Lu, Jimmy / Lamer, Tess / Vuong, Wayne / van Belkum, Marco J / McKay, Ryan T / Tyrrell, D Lorne / Vederas, John C / Young, Howard S / Lemieux, M Joanne

    Journal of molecular biology

    2021  Volume 433, Issue 13, Page(s) 167003

    Abstract: The main protease ( ... ...

    Abstract The main protease (M
    MeSH term(s) Animals ; Antiviral Agents/chemistry ; Antiviral Agents/pharmacology ; Cats ; Coronavirus 3C Proteases/antagonists & inhibitors ; Coronavirus 3C Proteases/chemistry ; Coronavirus 3C Proteases/metabolism ; Molecular Docking Simulation ; Protease Inhibitors/chemistry ; Protease Inhibitors/pharmacology ; Pyrrolidines/chemistry ; Pyrrolidines/pharmacology ; SARS-CoV-2/drug effects ; SARS-CoV-2/enzymology ; Sulfonic Acids ; Thermodynamics ; Viral Nonstructural Proteins/chemistry ; COVID-19 Drug Treatment
    Chemical Substances Antiviral Agents ; Protease Inhibitors ; Pyrrolidines ; Sulfonic Acids ; Viral Nonstructural Proteins ; 3C-like protease, SARS coronavirus (EC 3.4.22.-) ; Coronavirus 3C Proteases (EC 3.4.22.28) ; GC376 (H1NMJ5XDG5)
    Language English
    Publishing date 2021-04-22
    Publishing country Netherlands
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 80229-3
    ISSN 1089-8638 ; 0022-2836
    ISSN (online) 1089-8638
    ISSN 0022-2836
    DOI 10.1016/j.jmb.2021.167003
    Database MEDical Literature Analysis and Retrieval System OnLINE

    Full text online

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 867: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  6. Article ; Online: Synthesis of Chiral Spin-Labeled Amino Acids.

    Vuong, Wayne / Mosquera-Guagua, Fabricio / Sanichar, Randy / McDonald, Tyler R / Ernst, Oliver P / Wang, Lei / Vederas, John C

    Organic letters

    2019  Volume 21, Issue 24, Page(s) 10149–10153

    Abstract: Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance ... ...

    Abstract Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.
    MeSH term(s) Amino Acids/chemical synthesis ; Amino Acids/chemistry ; Molecular Structure ; Spin Labels ; Stereoisomerism
    Chemical Substances Amino Acids ; Spin Labels
    Language English
    Publishing date 2019-12-10
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b04216
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Peptidomimetic nitrile warheads as SARS-CoV-2 3CL protease inhibitors.

    Bai, Bing / Arutyunova, Elena / Khan, Muhammad Bashir / Lu, Jimmy / Joyce, Michael A / Saffran, Holly A / Shields, Justin A / Kandadai, Appan Srinivas / Belovodskiy, Alexandr / Hena, Mostofa / Vuong, Wayne / Lamer, Tess / Young, Howard S / Vederas, John C / Tyrrell, D Lorne / Lemieux, M Joanne / Nieman, James A

    RSC medicinal chemistry

    2021  Volume 12, Issue 10, Page(s) 1722–1730

    Abstract: Tragically, the death toll from the COVID-19 pandemic continues to rise, and with variants being observed around the globe new therapeutics, particularly direct-acting antivirals that are easily administered, are desperately needed. Studies targeting the ...

    Abstract Tragically, the death toll from the COVID-19 pandemic continues to rise, and with variants being observed around the globe new therapeutics, particularly direct-acting antivirals that are easily administered, are desperately needed. Studies targeting the SARS-CoV-2 3CL protease, which is critical for viral replication, with different peptidomimetics and warheads is an active area of research for development of potential drugs. To date, however, only a few publications have evaluated the nitrile warhead as a viral 3CL protease inhibitor, with only modest activity reported. This article describes our investigation of P3 4-methoxyindole peptidomimetic analogs with select P1 and P2 groups with a nitrile warhead that are potent inhibitors of SARS-CoV-2 3CL protease and demonstrate
    Language English
    Publishing date 2021-08-20
    Publishing country England
    Document type Journal Article
    ISSN 2632-8682
    ISSN (online) 2632-8682
    DOI 10.1039/d1md00247c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Synthesis of Chiral Spin-Labeled Amino Acids

    Vuong, Wayne / Ernst, Oliver P / McDonald, Tyler R / Mosquera-Guagua, Fabricio / Sanichar, Randy / Vederas, John C / Wang, Lei

    Organic letters. 2019 Dec. 10, v. 21, no. 24

    2019  

    Abstract: Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron–electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance ... ...

    Abstract Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron–electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.
    Keywords amino acids ; chemical reactions ; chemical structure ; enantioselective synthesis ; organic compounds ; peptides ; proteins
    Language English
    Dates of publication 2019-1210
    Size p. 10149-10153.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b04216
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  9. Article ; Online: Improved SARS-CoV-2 M

    Vuong, Wayne / Fischer, Conrad / Khan, Muhammad Bashir / van Belkum, Marco J / Lamer, Tess / Willoughby, Kurtis D / Lu, Jimmy / Arutyunova, Elena / Joyce, Michael A / Saffran, Holly A / Shields, Justin A / Young, Howard S / Nieman, James A / Tyrrell, D Lorne / Lemieux, M Joanne / Vederas, John C

    European journal of medicinal chemistry

    2021  Volume 222, Page(s) 113584

    Abstract: Replication of SARS-CoV-2, the coronavirus causing COVID-19, requires a main protease ( ... ...

    Abstract Replication of SARS-CoV-2, the coronavirus causing COVID-19, requires a main protease (M
    MeSH term(s) Animals ; Antiviral Agents/chemical synthesis ; Antiviral Agents/metabolism ; Antiviral Agents/pharmacology ; Binding Sites ; Chlorocebus aethiops ; Coronavirus 3C Proteases/antagonists & inhibitors ; Coronavirus 3C Proteases/chemistry ; Coronavirus 3C Proteases/metabolism ; Crystallography, X-Ray ; Cysteine Proteinase Inhibitors/chemical synthesis ; Cysteine Proteinase Inhibitors/metabolism ; Cysteine Proteinase Inhibitors/pharmacology ; Humans ; Micelles ; Microbial Sensitivity Tests ; Molecular Structure ; Protein Binding ; Pyrrolidines/chemical synthesis ; Pyrrolidines/metabolism ; Pyrrolidines/pharmacology ; SARS-CoV-2/drug effects ; SARS-CoV-2/enzymology ; Solubility ; Structure-Activity Relationship ; Sulfonic Acids/chemical synthesis ; Sulfonic Acids/metabolism ; Sulfonic Acids/pharmacology ; Vero Cells
    Chemical Substances Antiviral Agents ; Cysteine Proteinase Inhibitors ; Micelles ; Pyrrolidines ; Sulfonic Acids ; 3C-like proteinase, SARS-CoV-2 (EC 3.4.22.-) ; Coronavirus 3C Proteases (EC 3.4.22.28) ; GC376 (H1NMJ5XDG5)
    Language English
    Publishing date 2021-05-30
    Publishing country France
    Document type Journal Article ; Review
    ZDB-ID 188597-2
    ISSN 1768-3254 ; 0009-4374 ; 0223-5234
    ISSN (online) 1768-3254
    ISSN 0009-4374 ; 0223-5234
    DOI 10.1016/j.ejmech.2021.113584
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    In stock of ZB MED Cologne/Königswinter

    Zs.B 784: Show issues Location:
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  10. Article ; Online: Author Correction: Feline coronavirus drug inhibits the main protease of SARS-CoV-2 and blocks virus replication.

    Vuong, Wayne / Khan, Muhammad Bashir / Fischer, Conrad / Arutyunova, Elena / Lamer, Tess / Shields, Justin / Saffran, Holly A / McKay, Ryan T / van Belkum, Marco J / Joyce, Michael A / Young, Howard S / Tyrrell, D Lorne / Vederas, John C / Lemieux, M Joanne

    Nature communications

    2020  Volume 11, Issue 1, Page(s) 5409

    Abstract: An amendment to this paper has been published and can be accessed via a link at the top of the paper. ...

    Abstract An amendment to this paper has been published and can be accessed via a link at the top of the paper.
    Keywords covid19
    Language English
    Publishing date 2020-10-20
    Publishing country England
    Document type Published Erratum
    ZDB-ID 2553671-0
    ISSN 2041-1723 ; 2041-1723
    ISSN (online) 2041-1723
    ISSN 2041-1723
    DOI 10.1038/s41467-020-19339-y
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