Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation
- 2 December 2002
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 8 (23) , 5288-5295
- https://doi.org/10.1002/1521-3765(20021202)8:23<5288::aid-chem5288>3.0.co;2-f
Abstract
Starting from a thorough investigation of mechanistic aspects of ThDP‐dependent (ThDP=thiamin diphosphate) enzymes in combination with mutagenesis studies and a detailed substrate screening, new general synthetic methods have been developed based on Umpolung reactions by thiamin catalysis. A selective donor–acceptor concept was established leading to the first asymmetric cross‐benzoin condensation, and a kinetic racemic resolution through CC bond cleavage was developed. With these tools and in combination with protein engineering, we approached the synthesis of new chiral building blocks on a preparative scale. An outlook is given with respect to the potential of other ThDP‐dependent enzymes as catalysts in asymmetric synthesis.Keywords
This publication has 8 references indexed in Scilit:
- Development of a Donor−Acceptor Concept for Enzymatic Cross-Coupling Reactions of Aldehydes: The First Asymmetric Cross-Benzoin CondensationJournal of the American Chemical Society, 2002
- Kanosamine Biosynthesis: A Likely Source of the Aminoshikimate Pathway's Nitrogen AtomJournal of the American Chemical Society, 2002
- A Highly Enantioselective Catalytic Intramolecular Stetter ReactionJournal of the American Chemical Society, 2002
- Biosynthesis of 1-Deoxy-1-imino-d-erythrose 4-Phosphate: A Defining Metabolite in the Aminoshikimate PathwayJournal of the American Chemical Society, 2002
- Synthesis of α-Amido Ketones via Organic Catalysis: Thiazolium-Catalyzed Cross-Coupling of Aldehydes with AcyliminesJournal of the American Chemical Society, 2001
- Enzyme-Assisted Preparation of Isotope-Labeled 1-Deoxy-d-xylulose 5-PhosphateThe Journal of Organic Chemistry, 2001
- Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C–C bond cleavageJournal of the Chemical Society, Perkin Transactions 1, 2001
- Stereoselective Formation of Bis(α-hydroxy ketones) via Enzymatic CarboligationThe Journal of Organic Chemistry, 2000