Monofluoroalkenes are fluorinated motifs that can be used to replace amide bonds. In order to be incorporated into peptides, it is normally necessary to first synthesize a dipeptide where the amide bond has been replaced with a monofluoroalkene. In that context, this review will present the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres described since 2007. Some applications of those compounds will also be presented.
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http://dx.doi.org/10.3762/bjoc.13.262 | DOI Listing |
Acc Chem Res
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.
ConspectusChiral organosilicon compounds bearing a Si-stereogenic center have attracted increasing attention in various scientific communities and appear to be a topic of high current relevance in modern organic chemistry, given their versatile utility as chiral building blocks, chiral reagents, chiral auxiliaries, and chiral catalysts. Historically, access to these non-natural Si-stereogenic silanes mainly relies on resolution, whereas their asymmetric synthetic methods dramatically lagged compared to their carbon counterparts. Over the past two decades, transition-metal-catalyzed desymmetrization of prochiral organosilanes has emerged as an effective tool for the synthesis of enantioenriched Si-stereogenic silanes.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, Hunan, China.
The development of efficient immobilization support for the enhancement of enzyme activity and recyclability is a highly desirable objective. Single-crystalline ordered macro-microporous ZIF-8 (SOM-ZIF-8), has emerged as a highly effective matrix for enzyme immobilization, however, the inherent hydrophobic nature limits its further advancement. Herein, we have customized the immobilization of the Pseudomonas cepacia lipase (LP) in the modification-channels of SOM-ZIF-8 by functionalizing the inner surface-properties with polyethylene glycol (PEG) (LP@SOM-ZIF-8-PEG), and significant enhancement of the activity and (thermal, solvent and cyclic) stability can be realized.
View Article and Find Full Text PDFOrg Lett
January 2025
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, and College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, China.
An enantioselective oxypalladation/malononitrile addition cascade reaction of alkyne-tethered malononitriles was reported to synthesize enaminones bearing an all-carbon quaternary center. Using Pd(TFA)/Pyox as a precatalyst, an array of enaminone products were obtained in moderate overall yields, with excellent er (93.5:6.
View Article and Find Full Text PDFJ Chromatogr A
January 2025
Chemistry Department, Faculty of Science, Taibah University, Yanbu, Saudi Arabia; Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt. Electronic address:
Indoprofen (INP) comprises two enantiomers, R- and S-, whose high pharmacological efficacy is realized only in the case of the separated enantiomers. A newly synthesized poly(acrylonitrile-co-divinylbenzene) (PANB)-based sorbent with selective affinity to the S-enantiomer of INP was applied to separate INP racemate. The synthesis was performed by suspension polymerization with low-crosslinked PANB microparticles and by reaction of the inserted nitriles with 1-amino-1H-pyrrole-2,5‑dione (Ma-NH).
View Article and Find Full Text PDFPhys Chem Chem Phys
January 2025
Laboratoire Softmat, UMR au CNRS no 5623, Université Paul Sabatier, F-31062 Toulouse, France.
Simulations on an ODE-based model shows that there are many common points between Viedma deracemization and chiral self-assemblies of achiral building blocks towards chiral nanoparticles. Both systems occur in a closed system with energy exchange but no matter exchange with the surroundings and show parallel reversible growth mechanisms which coexist with an irreversible cluster breaking (grinding). The various mechanisms of growth give rise to the formation of polymerization/depolymerization cycles while the consecutive transformation of achiral monomer into chiral cluster results into an indirect enantioselective autocatalysis.
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