100 Jahre Max‐Planck‐Institut für Kohlenforschung

Reetz, Manfred T.

doi:10.1002/ange.201403217

Cited by 4 publications

(1 citation statement)

References 225 publications

(151 reference statements)

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“…The PBE0 hybrid functional and the D3BJ dispersion correction were used in conjunction with the RIJCOSX approximation to account for the solvent effect of the aqueous solution using the conductor-like polarizable continuum model (CPCM) [ 35 , 36 ]. Time-dependent density functional theory (TD-DFT) calculations were run in Orca and used to generate simulated UV-Vis absorption spectra of free 2-TU and the 2-TU-Au complexes [ 37 , 38 , 39 ]. Eigenvalues of frontier molecular orbitals (FMOs) from self-consistent field (ΔSCF) calculations were then used to calculate the HOMO-LUMO energy gaps of the free 2-TU and the 2-TU-Au complexes [ 40 , 41 , 42 ].…”

Section: Methodsmentioning

confidence: 99%

Experimental and Theoretical Screening of Core Gold Nanoparticles and Their Binding Mechanism to an Anticancer Drug, 2-Thiouracil

Lorenzana-Vázquez,

Adams,

Reyna

et al. 2023

Molecules

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This study demonstrated the capability of two readily available optical spectroscopy tools, namely UV-Vis absorption spectrophotometry and Raman/surface-enhanced Raman spectroscopy, to select in a rapid and noninvasive manner the most homogenous gold nanoparticle (AuNP) models and to identify their chemical binding mechanism to 2-thiouracil (2-TU). 2-TU is an anticancer drug of great promise in the antiproliferative and photothermal therapies of cancer. The citrate-capped AuNPs emerged as the most stable as well as time- and cost-effective AuNP model out of the three widely used colloidal nanocores (citrate-, borohydride-citrate-, and sodium dodecyl sulfate (SDS)-capped AuNPs) that were examined. 2-TU chemically attached to the relatively monodispersed AuNPs via a chemisorption mechanism. The 2-TU-AuNPs complex formed through the covalent bonding of the S atom of 2-TU to the nanosurface in a vertical orientation. The spectroscopic results were then confirmed with the help of density functional theory (DFT) calculations and other physicochemical characterization tools for nanomaterials such as transmission electron microscopy (TEM), dynamic light scattering (DLS), and zeta potential. Overall, the purified 2-TU-AuNPs were found to be spherical, had an average diameter of 25 ± 2 nm, a narrow size distribution (1–30 nm), a sharp localized surface plasmon resonance (LSPR) peak at 525 nm, and a negative surface charge (−14 mV).

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Section: Methodsmentioning

confidence: 99%

Experimental and Theoretical Screening of Core Gold Nanoparticles and Their Binding Mechanism to an Anticancer Drug, 2-Thiouracil

Lorenzana-Vázquez,

Adams,

Reyna

et al. 2023

Molecules

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Chiral Imidodiphosphoric Acids‐Catalyzed Friedel–Crafts Reactions of Indoles/Pyrroles with 3‐Hydroxy‐indolyloxindoles: Enantioselective Synthesis of 3,3‐Diaryloxindoles

Zhuo

Song

et al. 2016

Adv Synth Catal

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Thef irst enantioselective Friedel-Crafts alkylation of indoles and pyrroles with 3-hydroxy-3-indolyloxindoles to access twon ovelt ypes of 3,3-diaryloxindoles catalyzed by chiral imidodiphosphoric acids hasb een reported. Ar ange of quaternary carbon centered 3,3-diaryloxindoles were synthesized in high yield (up to > 99%) with excellent enantioselectivity (up to 98% ee)a tl ow catalyst loadings (as low as 0.5 mol%). TheF riedel-Crafts reaction between indoles and 3-hydroxy-3-indolyloxindoles is amenable to gram scale syntheses.

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Witnessing the Birth of Directed Evolution of Stereoselective Enzymes as Catalysts in Organic Chemistry

Reetz

2022

Adv Synth Catal

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This invited essay outlines how the idea of directed evolution of stereoselective enzymes was born and implemented experimentally at the Max-Planck-Institut für Kohlenforschung in Mülheim/ Germany during the period 1994-1998, a time when Andreas Pfaltz was present in the Institute. As the new and sole director of the MPI, I initiated new research projects, and also started to restructure the Institute with the establishment of five departments, all dedicated to some form of catalysis and to be led by five independent directors. Andreas Pfaltz was the first director whom I hired, heading the Department of Homogeneous Catalysis. During his stay in Mülheim until 1998, the Pfaltz group invented effective chiral ligands for a number of particularly challenging enantioselective transformations. During this period, Andreas Pfaltz witnessed the birth and development of directed evolution of stereoselective enzymes as a new research direction in the Reetz group. Indeed, he was one of the very few organic chemists who realized at the time that a door to a novel research area had been opened. The widespread application of enzymes was hampered for decades due to limited enantio-, diastereo-, and regioselectivity, which was the reason why organic chemists were not interested in biocatalysis. This attitude slowly changed with the advent of directed evolution of stereoselective enzymes in 1997, in a publication from the Reetz group. Methodology development with emphasis on stereo-and regioselectivity as well as activity followed, the techniques and strategies becoming more and more rational. Today, semirational approaches and so-called rational enzyme design have merged, as evidenced, inter alia, by the development of focused rational iterative site-specific mutagenesis (FRISM). The toolbox of organic chemists now includes enzymes, primarily because the possibility of controlling stereoselectivity by protein engineering has ensured reliability when facing synthetic challenges. 1. Introductory Remarks 2. The Birth of Directed Evolution of Stereoselective Enzymes 3. The Crucial Role of Methodology Development in Directed Evolution of Selective Enzymes as Catalysts in Organic Chemistry 4. Final Message

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100 Jahre Max‐Planck‐Institut für Kohlenforschung

Cited by 4 publications

References 225 publications

Experimental and Theoretical Screening of Core Gold Nanoparticles and Their Binding Mechanism to an Anticancer Drug, 2-Thiouracil

Experimental and Theoretical Screening of Core Gold Nanoparticles and Their Binding Mechanism to an Anticancer Drug, 2-Thiouracil

Chiral Imidodiphosphoric Acids‐Catalyzed Friedel–Crafts Reactions of Indoles/Pyrroles with 3‐Hydroxy‐indolyloxindoles: Enantioselective Synthesis of 3,3‐Diaryloxindoles

Witnessing the Birth of Directed Evolution of Stereoselective Enzymes as Catalysts in Organic Chemistry

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