Carleton Author

Alberg, David G.

Department

Chemistry

Journal Title

Bioorganic and Medicinal Chemistry Letters

Publication Date

2009

Volume

19

First Page

3888

Publisher

Elsevier

Last Page

3891

File Name

046_Alberg-David_OrganocatalysisWithEndogenousCompounds.pdf

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.

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's 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

Contributing Organization

Carleton College

Type

Article

Format

application/pdf

Language

English

Included in

Chemistry Commons

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