54899-03-5Relevant articles and documents
Molecular Recognition and Cocrystallization of Methylated and Halogenated Fragments of Danicalipin A by Enantiopure Alleno-Acetylenic Cage Receptors
Carreira, Erick M.,Diederich, Fran?ois,Fischer, Stefan,Gropp, Cornelius,Husch, Tamara,Trapp, Nils
supporting information, (2020/03/13)
Enantiopure (P)4- and (M)4-configured alleno-acetylenic cage (AAC) receptors offer a highly defined interior for the complexation and structure elucidation of small molecule fragments of the stereochemically complex chlorosulfolipid danicalipin A. Solution (NMR), solid state (X-ray), and theoretical investigations of the formed host-guest complexes provide insight into the conformational preferences of 14 achiral and chiral derivatives of the danicalipin A chlorohydrin core in a confined, mostly hydrophobic environment, extending previously reported studies in polar solvents. The conserved binding mode of the guests permits deciphering the effect of functional group replacements on Gibbs binding energies ΔG. A strong contribution of conformational energies toward the binding affinities is revealed, which explains why the denser packing of larger apolar domains of the guests does not necessarily lead to higher association. Enantioselective binding of chiral guests, with energetic differences ΔΔG293 K up to 0.7 kcal mol-1 between diastereoisomeric complexes, is explained by hydrogen- and halogen-bonding, as well as dispersion interactions. Calorimetric studies (ITC) show that the stronger binding of one enantiomer is accompanied by an increased gain in enthalpy ΔH but at the cost of a larger entropic penalty TΔS stemming from tighter binding.
Discovery of PF-06835919: A Potent Inhibitor of Ketohexokinase (KHK) for the Treatment of Metabolic Disorders Driven by the Overconsumption of Fructose
Futatsugi, Kentaro,Smith, Aaron C.,Tu, Meihua,Raymer, Brian,Ahn, Kay,Coffey, Steven B.,Dowling, Matthew S.,Fernando, Dilinie P.,Gutierrez, Jemy A.,Huard, Kim,Jasti, Jayasankar,Kalgutkar, Amit S.,Knafels, John D.,Pandit, Jayvardhan,Parris, Kevin D.,Perez, Sylvie,Pfefferkorn, Jeffrey A.,Price, David A.,Ryder, Tim,Shavnya, Andre,Stock, Ingrid A.,Tsai, Andy S.,Tesz, Gregory J.,Thuma, Benjamin A.,Weng, Yan,Wisniewska, Hanna M.,Xing, Gang,Zhou, Jun,Magee, Thomas V.
, p. 13546 - 13560 (2021/01/01)
Increased fructose consumption and its subsequent metabolism have been implicated in metabolic disorders such as nonalcoholic fatty liver disease and steatohepatitis (NAFLD/NASH) and insulin resistance. Ketohexokinase (KHK) converts fructose to fructose-1
SUBSTITUTED 3-AZABICYCLO[3.1.0]HEXANES AS KETOHEXOKINASE INHIBITORS
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Paragraph 0274; 0275, (2017/07/14)
Provided herein are substituted 3-azabicyclo[3.1.0]hexanes as ketohexokinase inhibitors, processes to make said compounds, and methods comprising administering said compounds to a mammal in need thereof.
Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A
Landry, Matthew L.,Hu, Dennis X.,McKenna, Grace M.,Burns, Noah Z.
supporting information, p. 5150 - 5158 (2016/05/19)
A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosulfolipids is reported. The described dichlorination and dibromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.
Organocatalytic diastereoselective dibromination of alkenes
Zhu, Mingzhao,Lin, Shuangzheng,Zhao, Gui-Ling,Sun, Junliang,Córdova, Armando
experimental part, p. 2708 - 2712 (2010/07/04)
A highly diastereoselective pyrrolidine-promoted dibromination of alkenes by combination of NBS and succinimide is presented. The pyrrolidine-mediated dibromination of alkenes is higly anti-selective and gives the corresponding products in moderate to high yields and up to >25:1 dr.
An asymmetric total synthesis of brevisamide
Ghosh, Arun K.,Li, Jianfeng
supporting information; experimental part, p. 4164 - 4167 (2009/12/31)
An enantioselective synthesis of marine alkaloid brevisamide was accomplished in a convergent manner. The synthesis utilized an enantioselective hetero-Diels - Alder reaction which sets three chiral centers in compound 11. The synthesis also features a modified Wolff-Kishner reduction, Rubottom oxidation, and Suzuki - Miyaura coupling to furnish brevisamide.
Enantioselective synthesis of the C14-C25 portion of the cytotoxic natural product, amphidinolide B1
Lee, Duck-Hyung,Rho, Man-Dong
, p. 2573 - 2576 (2007/10/03)
The C14-C25 portion of the cytotoxic natural product, amphidinolide B1 (1), was synthesized enantioselectively using Myers asymmetric alkylation protocol, epoxide opening with higher order cuprate, Sharpless asymmetric epoxidation of allylic alcohol 17, a
