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Literature DB >> 29971313

Application of Q2MM to predictions in stereoselective synthesis.

Anthony R Rosales¹, Taylor R Quinn, Jessica Wahlers, Anna Tomberg, Xin Zhang, Paul Helquist, Olaf Wiest, Per-Ola Norrby.

Abstract

Quantum-Guided Molecular Mechanics (Q2MM) can be used to derive transition state force fields (TSFFs) that allow the fast and accurate predictions of stereoselectivity for a wide range of catalytic enantioselective reactions. The basic ideas behind the derivation of TSFFs using Q2MM are discussed and the steps involved in obtaining a TSFF using the Q2MM code, publically available at github.com/q2mm, are shown. The applicability for a range of reactions, including several non-standard applications of Q2MM, is demonstrated. Future developments of the method are also discussed.

Entities: CellLine Chemical Disease Gene Species

Year: 2018 PMID： 29971313 PMCID： PMC6069518 DOI： 10.1039/c8cc03695k

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

54 in total

Review 1. Force fields for protein simulations.

Authors: Jay W Ponder; David A Case
Journal: Adv Protein Chem Date: 2003

2. A priori theoretical prediction of selectivity in asymmetric catalysis: design of chiral catalysts by using quantum molecular interaction fields.

Authors: James C Ianni; Venkatachalam Annamalai; Puay-Wah Phuan; Manoranjan Panda; Marisa C Kozlowski
Journal: Angew Chem Int Ed Engl Date: 2006-08-18 Impact factor: 15.336

3. Toward a computational tool predicting the stereochemical outcome of asymmetric reactions: development of the molecular mechanics-based program ACE and application to asymmetric epoxidation reactions.

Authors: Nathanael Weill; Christopher R Corbeil; Joris W De Schutter; Nicolas Moitessier
Journal: J Comput Chem Date: 2011-07-06 Impact factor: 3.376

4. The Evolution of Chemical High-Throughput Experimentation To Address Challenging Problems in Pharmaceutical Synthesis.

Authors: Shane W Krska; Daniel A DiRocco; Spencer D Dreher; Michael Shevlin
Journal: Acc Chem Res Date: 2017-11-27 Impact factor: 22.384

5. Current status of protein force fields for molecular dynamics simulations.

Authors: Pedro E M Lopes; Olgun Guvench; Alexander D MacKerell
Journal: Methods Mol Biol Date: 2015

6. Why are BINOL-based monophosphites such efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation?

Authors: Manfred T Reetz; Andreas Meiswinkel; Gerlinde Mehler; Klaus Angermund; Martin Graf; Walter Thiel; Richard Mynott; Donna G Blackmond
Journal: J Am Chem Soc Date: 2005-07-27 Impact factor: 15.419

7. Atomistic-scale simulations of the initial chemical events in the thermal initiation of triacetonetriperoxide.

Authors: Adri C T van Duin; Yehuda Zeiri; Faina Dubnikova; Ronnie Kosloff; William A Goddard
Journal: J Am Chem Soc Date: 2005-08-10 Impact factor: 15.419

8. On the role of the axial ligand in heme proteins: a theoretical study.

Authors: Patrik Rydberg; Emma Sigfridsson; Ulf Ryde
Journal: J Biol Inorg Chem Date: 2004-01-15 Impact factor: 3.358

9. Development of a Q2MM Force Field for the Asymmetric Rhodium Catalyzed Hydrogenation of Enamides.

Authors: Patrick J Donoghue; Paul Helquist; Per-Ola Norrby; Olaf Wiest
Journal: J Chem Theory Comput Date: 2008-08 Impact factor: 6.006

10. Stereoselectivity in Asymmetric Catalysis: The Case of Ruthenium-Catalyzed Ketone Hydrogenation.

Authors: Elaine Limé; Michelle D Lundholm; Aaron Forbes; Olaf Wiest; Paul Helquist; Per-Ola Norrby
Journal: J Chem Theory Comput Date: 2014-06-10 Impact factor: 6.006

9 in total

1. Machine learning and semi-empirical calculations: a synergistic approach to rapid, accurate, and mechanism-based reaction barrier prediction.

Authors: Elliot H E Farrar; Matthew N Grayson
Journal: Chem Sci Date: 2022-06-14 Impact factor: 9.969

Application of Q2MM to predictions in stereoselective synthesis.

Review 1. Force fields for protein simulations.

2. A priori theoretical prediction of selectivity in asymmetric catalysis: design of chiral catalysts by using quantum molecular interaction fields.

3. Toward a computational tool predicting the stereochemical outcome of asymmetric reactions: development of the molecular mechanics-based program ACE and application to asymmetric epoxidation reactions.

4. The Evolution of Chemical High-Throughput Experimentation To Address Challenging Problems in Pharmaceutical Synthesis.

5. Current status of protein force fields for molecular dynamics simulations.

6. Why are BINOL-based monophosphites such efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation?

7. Atomistic-scale simulations of the initial chemical events in the thermal initiation of triacetonetriperoxide.

8. On the role of the axial ligand in heme proteins: a theoretical study.

9. Development of a Q2MM Force Field for the Asymmetric Rhodium Catalyzed Hydrogenation of Enamides.

10. Stereoselectivity in Asymmetric Catalysis: The Case of Ruthenium-Catalyzed Ketone Hydrogenation.

1. Machine learning and semi-empirical calculations: a synergistic approach to rapid, accurate, and mechanism-based reaction barrier prediction.

2. The (not so) simple prediction of enantioselectivity - a pipeline for high-fidelity computations.

3. Transition State Force Field for the Asymmetric Redox-Relay Heck Reaction.

Review 4. Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

5. Stereoselectivity Predictions for the Pd-Catalyzed 1,4-Conjugate Addition Using Quantum-Guided Molecular Mechanics.

6. Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

7. Microsecond timescale MD simulations at the transition state of PmHMGR predict remote allosteric residues.

8. Proofreading experimentally assigned stereochemistry through Q2MM predictions in Pd-catalyzed allylic aminations.

9. Automated fitting of transition state force fields for biomolecular simulations.