33878-99-8Relevant articles and documents
Antibody-catalyzed enantioselective Robinson annulation
Zhong,Hoffmann,Lerner,Danishefsky,Barbas III
, p. 8131 - 8132 (1997)
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Proline mediated asymmetric ketol cyclization: A template reaction
Rajagopal,Moni,Subramanian,Swaminathan
, p. 1631 - 1634 (1999)
1H, 13C and ATR-FTIR Spectroscopic studies reveal that the asymmetric cyclization of prochiral triones 1 and 2 in the presence of S-proline is a template reaction.
Identification of Inhibitors of Cholesterol Transport Proteins Through the Synthesis of a Diverse, Sterol-Inspired Compound Collection
Laraia, Luca,Olsen, Asger Hegelund,Whitmarsh-Everiss, Thomas
supporting information, p. 26755 - 26761 (2021/11/17)
Cholesterol transport proteins regulate a vast array of cellular processes including lipid metabolism, vesicular and non-vesicular trafficking, organelle contact sites, and autophagy. Despite their undoubted importance, the identification of selective modulators of this class of proteins has been challenging due to the structural similarities in the cholesterol-binding site. Herein we report a general strategy for the identification of selective inhibitors of cholesterol transport proteins via the synthesis of a diverse sterol-inspired compound collection. Fusion of a primary sterol fragment to an array of secondary privileged scaffolds led to the identification of potent and selective inhibitors of the cholesterol transport protein Aster-C, which displayed a surprising preference for the unnatural-sterol AB-ring stereochemistry and new inhibitors of Aster-A. We propose that this strategy can and should be applied to any therapeutically relevant sterol-binding protein.
Assessing the Recyclability of Supramolecularly Assembled Organocatalytic Species: A Theoretical Insight
Llorens, Lluis,Llanes, Patricia,Fianchini, Mauro,Pericàs, Miquel A.
, p. 475 - 484 (2020/03/19)
Asymmetric organocatalytic synthesis is a powerful tool in organic chemistry to achieve desired stereoisomers in high purity via mild catalytic routes. The immobilization of homogeneous catalytic species onto heterogeneous phases embodies the evolution of asymmetric catalysis, since it allows the recycling of the catalyst for several runs until degradation. Previously reported non-covalent immobilization of proline-based catalysts for aldol reaction onto magnetic nanoparticles functionalized with β-cyclodextrin (MNP-β-CB) demonstrated the viability of the methodology. This paper proposes two new catalyst recycling strategies based on Cucurbit[7]uril (CB[7]) for the aldol reaction and the Robinson annulation. These recycling methodologies are conceptually different. The former relies on the homogeneous encapsulation of the catalyst in cucurbituril, CB[7] ? Cat, and its recycling in the aqueous phase by extraction of the aldol product with organic solvents. The latter relies on the heterogeneous encapsulation of the catalyst as MNP-CB[7] ? Cat2 system and its recycling by magnetic harvesting. Density functional theory (DFT) calculations have been employed to rationalize the thermodynamics of experimental results, and to suggest caveats and plausible improvements in view of a future catalytic design.
