Type
Article
Keywords
Organocatalysis, Aldol, Non-enzymatic, Acetone, Methylglyoxal
Abstract
The aldol reaction of the endogeneous compounds acetone and methylglyoxal has been studied using organocatalysis in relation to biologically relevant non-enzymatic reactions. Under preparative conditions, 3-hydroxy-2,5-hexadione, known as Henze’s ketol, is formed in high yield and with enantioselectivities up to 88% ee. Furthermore, Henze’s ketol is also formed under simulated physiological conditions at micromolar scale, indicating that this reaction might take place in living organisms.
Language
English
Department(s)
Chemistry
Journal or Book Title
Bioorganic and Medicinal Chemistry Letters
Publication Year
2009
DOI
10.1016/j.bmcl.2009.03.128
Publisher
Elsevier
Rights Management
Carleton College does not own the copyright to this work and the work is available through the Carleton College Library following the original publisher policies regarding self-archiving. For more information on the copyright status of this work, refer to the current copyright holder.
RoMEO Color
Green
Preprint Archiving
Yes (with link to journal home page)
Postprint Archiving
Yes
Publisher PDF Archiving
No
Paid OA Option
Yes
Contributing Organization
Carleton College
Format
application/pdf
Recommended Citation
Alberg, David G., Thomas B. Poulsen, Søren Bertelsen, Kasper L. Christensen, Rune D. Birkler, Mogens Johannsen, and Karl A. Jørgensen., "Organocatalysis with Endogenous Compounds: Towards Novel Non-enzymatic Reactions". Bioorganic and Medicinal Chemistry Letters. 2009, 19: 3888-3891. Available at: https://doi.org/10.1016/j.bmcl.2009.03.128. Accessed via Faculty Work. Chemistry. Carleton Digital Commons. https://digitalcommons.carleton.edu/chem_faculty/10
The definitive version is available at https://doi.org/10.1016/j.bmcl.2009.03.128
