Synthesis of enantiomerically pure α-hydroxyaldehydes from the corresponding α-hydroxycarboxylic acids: novel substrates for Escherichia coli transketolase
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 24,p. 2475-2476
- https://doi.org/10.1039/c39950002475
Abstract
Enantiomerically pure (R)-α-hydroxyaldehydes (>95% ee) are prepared from the corresponding α-hydroxyesters by silyl protection, reduction with diisobutylaluminium hydride, and finally deprotection under acidic conditions; subsequent coupling of these aldehydes with lithium hydroxypyruvate, catalysed by Escherichia coli transketolase, leads to novel optically pure triols.Keywords
This publication has 10 references indexed in Scilit:
- A novel bicyclic orthoester as a chiral auxiliary: Application to the synthesis of α-hydroxy acidsTetrahedron Letters, 1995
- Asymmetric catalytic hydrogenation of α-ketoesters using new chiral Ru(II)(AMPP) complexesTetrahedron: Asymmetry, 1995
- Reduction of α-trialkylsiloxy nitriles with diisobutylaluminium hydride (DIBAH): A facile preparation of α-trialkylsiloxy aldehydes and their derivativesTetrahedron, 1994
- Enzyme-catalysed carbon–carbon bond formation: use of transketolase from Escherichia coliJournal of the Chemical Society, Perkin Transactions 1, 1993
- Synthesis of 15N-labelled chiral Boc-amino acids from triflates: enantiomers of leucine and phenylalanineJournal of the Chemical Society, Perkin Transactions 1, 1993
- Substrate specificity and carbohydrate synthesis using transketolaseThe Journal of Organic Chemistry, 1992
- Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolaseTetrahedron Letters, 1992
- Enzyme-catalyzed synthesis of carbohydrates: synthetic potential of transketolaseTetrahedron Letters, 1991
- The oxidative pentose phosphate cycle. I. Preparation of substrates and enzymesArchives of Biochemistry and Biophysics, 1958
- Configuration of Carbohydrates, Hydroxy-Acids and Amino-Acids: Stereochemical Standards of ConfigurationNature, 1950