Glyoxalase-based toolbox for the enantioselective synthesis of α-hydroxy carboxylic acids
Yedigenov, M., Amire, N., Abdirassil, A., Mulikova, T., Begenov, A., Kiesilä, A., Peshkov, A. A., Peshkov, V. A., & Utepbergenov, D. (2024). Glyoxalase-based toolbox for the enantioselective synthesis of α-hydroxy carboxylic acids. Organic and Biomolecular Chemistry, Advance Article. https://doi.org/10.1039/D3OB02098C
Published in
Organic and Biomolecular ChemistryAuthors
Date
2024Access restrictions
Embargoed until: 2025-02-10Request copy from author
Copyright
© 2024 Royal Society of Chemistry
We report highly enantioselective synthesis of L-α-hydroxy carboxylic acids (L-αHCAs) via enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of D-αHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of α-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.
Publisher
Royal Society of ChemistryISSN Search the Publication Forum
1477-0520Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/207171021
Metadata
Show full item recordCollections
Additional information about funding
This work was supported by Nazarbayev University CRP grant 091019CRP2121 to D. U. and FDCRGP grant 11022021FD2903 to V. P.License
Related items
Showing items with similar title or keywords.
-
Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl cluster : diastereomeric control of enantioselectivity
Abdel-Magied, Ahmed F.; Theibich, Yusuf; Singh, Amrendra K.; Rahaman, Ahibur; Doverbratt, Isa; Raha, Arun K.; Haukka, Matti; Richmond, Michael G.; Nordlander, Ebbe (Royal Society of Chemistry, 2020)Twenty clusters of the general formula [(μ-H)2Ru3(μ3-S)(CO)7(μ-P–P*)] (P–P* = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have been tested ... -
Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid
Kortet, Sami; Claraz, Aurélie; Pihko, Petri M. (American Chemical Society, 2020)A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama–Michael reaction and enamine-catalyzed organocatalytic α-chlorination ... -
Peptidoglykaanihydrolaasin siirtymätila-analogin synteesi
Kankkunen, Eveliina (2023)Tutkielmassa tutustutaan bakteerien rakenteeseen ja niiden kasvuun ja hajoamiseen vaikuttaviin tekijöihin. Aluksi perehdytään peptidoglykaanin rakenteeseen ja synteesiin, minkä jälkeen käsitellään peptidoglykaania hajottavia ... -
Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine
Jäger, Christina; Nieger, Martin; Rissanen, Kari; Deska, Jan (Wiley-VCH Verlag, 2023)The assembly of enzymatic cascades and multi-step reaction sequences represents an attractive alternative to traditional synthetic-organic approaches. The biocatalytic reaction mediators offer not only mild conditions and ... -
Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction
Straminelli, Leonardo; Vicentini, Francesco; Di Sabato, Antonio; Montone, Carmela Maria; Cavaliere, Chiara; Rissanen, Kari; Leonelli, Francesca; Vetica, Fabrizio (American Chemical Society (ACS), 2022)A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis ...