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  1. Article ; Online: Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins.

    Liu, Yi / Bender, Sophie G / Sorigue, Damien / Diaz, Daniel J / Ellington, Andrew D / Mann, Greg / Allmendinger, Simon / Hyster, Todd K

    Journal of the American Chemical Society

    2024  Volume 146, Issue 11, Page(s) 7191–7197

    Abstract: Photoenzymatic intermolecular hydroalkylations of olefins are highly enantioselective for chiral centers formed during radical termination but poorly selective for centers set in the C-C bond-forming event. Here, we report the evolution of a flavin- ... ...

    Abstract Photoenzymatic intermolecular hydroalkylations of olefins are highly enantioselective for chiral centers formed during radical termination but poorly selective for centers set in the C-C bond-forming event. Here, we report the evolution of a flavin-dependent "ene"-reductase to catalyze the coupling of α,α-dichloroamides with alkenes to afford α-chloroamides in good yield with excellent chemo- and stereoselectivity. These products can serve as linchpins in the synthesis of pharmaceutically valuable motifs. Mechanistic studies indicate that radical formation occurs by exciting a charge-transfer complex templated by the protein. Precise control over the orientation of molecules within the charge-transfer complex potentially accounts for the observed stereoselectivity. The work expands the types of motifs that can be prepared using photoenzymatic catalysis.
    MeSH term(s) Alkenes ; Catalysis
    Chemical Substances Alkenes
    Language English
    Publishing date 2024-03-05
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.4c00927
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Searching for an ideal SERM: Mining tamoxifen structure-activity relationships.

    Price, Sky / Bender, Sophie G / Yahn, Rachel / Till, Nicholas A / Varady, Sophia / LaLonde, Rebecca Lyn

    Bioorganic & medicinal chemistry letters

    2021  Volume 52, Page(s) 128383

    Abstract: The repurposing of old drugs for new treatments has recently garnered increased attention in the face of new diseases and declining productivity of the pharmaceutial industry. This report draws attention to potential opportunities hiding in plain sight ... ...

    Abstract The repurposing of old drugs for new treatments has recently garnered increased attention in the face of new diseases and declining productivity of the pharmaceutial industry. This report draws attention to potential opportunities hiding in plain sight within the SAR of off-patent drugs. Herein we explore the untapped potential of Selective Estrogen Receptor Modulators (SERMs). SERMs are a class of molecules that have been highly influential in the treatment of estrogen receptor-positive breast cancers. However, the most commonly prescribed SERM, tamoxifen, has been found to increase the risk of endometrial cancer. Another SERM, raloxifene, does not increase incidence of endometrial cancer, but has been abandoned as a breast cancer treatment. We report the design, synthesis, and evaluation of an unexplored tamoxifen substitution pattern which mimics the geometry of raloxifene to confer its favorable pharmacodynamics. This substitution pattern was found to maintain excellent binding affinity to estrogen receptor-α.
    MeSH term(s) Antineoplastic Agents, Hormonal/chemistry ; Antineoplastic Agents, Hormonal/pharmacology ; Breast Neoplasms/drug therapy ; Breast Neoplasms/metabolism ; Dose-Response Relationship, Drug ; Estrogen Receptor alpha/antagonists & inhibitors ; Estrogen Receptor alpha/metabolism ; Female ; Humans ; Molecular Structure ; Raloxifene Hydrochloride/chemistry ; Raloxifene Hydrochloride/pharmacology ; Selective Estrogen Receptor Modulators/chemistry ; Selective Estrogen Receptor Modulators/pharmacology ; Structure-Activity Relationship ; Tamoxifen/chemistry ; Tamoxifen/pharmacology
    Chemical Substances Antineoplastic Agents, Hormonal ; ESR1 protein, human ; Estrogen Receptor alpha ; Selective Estrogen Receptor Modulators ; Tamoxifen (094ZI81Y45) ; Raloxifene Hydrochloride (4F86W47BR6)
    Language English
    Publishing date 2021-09-27
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2021.128383
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Photobiocatalytic Strategies for Organic Synthesis.

    Emmanuel, Megan A / Bender, Sophie G / Bilodeau, Catherine / Carceller, Jose M / DeHovitz, Jacob S / Fu, Haigen / Liu, Yi / Nicholls, Bryce T / Ouyang, Yao / Page, Claire G / Qiao, Tianzhang / Raps, Felix C / Sorigué, Damien R / Sun, Shang-Zheng / Turek-Herman, Joshua / Ye, Yuxuan / Rivas-Souchet, Ariadna / Cao, Jingzhe / Hyster, Todd K

    Chemical reviews

    2023  Volume 123, Issue 9, Page(s) 5459–5520

    Abstract: Biocatalysis has revolutionized chemical synthesis, providing sustainable methods for preparing various organic molecules. In enzyme-mediated organic synthesis, most reactions involve molecules operating from their ground states. Over the past 25 years, ... ...

    Abstract Biocatalysis has revolutionized chemical synthesis, providing sustainable methods for preparing various organic molecules. In enzyme-mediated organic synthesis, most reactions involve molecules operating from their ground states. Over the past 25 years, there has been an increased interest in enzymatic processes that utilize electronically excited states accessed through photoexcitation. These photobiocatalytic processes involve a diverse array of reaction mechanisms that are complementary to one another. This comprehensive review will describe the state-of-the-art strategies in photobiocatalysis for organic synthesis until December 2022. Apart from reviewing the relevant literature, a central goal of this review is to delineate the mechanistic differences between the general strategies employed in the field. We will organize this review based on the relationship between the photochemical step and the enzymatic transformations. The review will include mechanistic studies, substrate scopes, and protein optimization strategies. By clearly defining mechanistically-distinct strategies in photobiocatalytic chemistry, we hope to illuminate future synthetic opportunities in the area.
    MeSH term(s) Biocatalysis ; Chemistry Techniques, Synthetic
    Language English
    Publishing date 2023-04-28
    Publishing country United States
    Document type Journal Article ; Review ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 207949-5
    ISSN 1520-6890 ; 0009-2665
    ISSN (online) 1520-6890
    ISSN 0009-2665
    DOI 10.1021/acs.chemrev.2c00767
    Database MEDical Literature Analysis and Retrieval System OnLINE

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