Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis

Heidlindemann M, Hammel M, Scheffler U, Mahrwald R, Hummel W, Berkessel A, Gröger H (2015)
The Journal of Organic Chemistry 80(7): 3387-3396.

Journal Article | Published | English

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Abstract
The combination of an asymmetric organocatalytic aldol reaction with a subsequent biotransformation toward a "one-pot-like" process for the synthesis of (R)-pantolactone, which to date is industrially produced by a resolution process, is demonstrated. This process consists of an initial aldol reaction catalyzed by readily available l-histidine followed by biotransformation of the aldol adduct by an alcohol dehydrogenase without the need for intermediate isolation. Employing the industrially attractive starting material isobutanal, a chemoenzymatic three-step process without intermediate purification is established allowing the synthesis of (R)-pantolactone in an overall yield of 55% (three steps) and high enantiomeric excess of 95%.
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Heidlindemann M, Hammel M, Scheffler U, et al. Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis. The Journal of Organic Chemistry. 2015;80(7):3387-3396.
Heidlindemann, M., Hammel, M., Scheffler, U., Mahrwald, R., Hummel, W., Berkessel, A., & Gröger, H. (2015). Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis. The Journal of Organic Chemistry, 80(7), 3387-3396.
Heidlindemann, M., Hammel, M., Scheffler, U., Mahrwald, R., Hummel, W., Berkessel, A., and Gröger, H. (2015). Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis. The Journal of Organic Chemistry 80, 3387-3396.
Heidlindemann, M., et al., 2015. Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis. The Journal of Organic Chemistry, 80(7), p 3387-3396.
M. Heidlindemann, et al., “Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis”, The Journal of Organic Chemistry, vol. 80, 2015, pp. 3387-3396.
Heidlindemann, M., Hammel, M., Scheffler, U., Mahrwald, R., Hummel, W., Berkessel, A., Gröger, H.: Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis. The Journal of Organic Chemistry. 80, 3387-3396 (2015).
Heidlindemann, Marcel, Hammel, Matthias, Scheffler, Ulf, Mahrwald, Rainer, Hummel, Werner, Berkessel, Albrecht, and Gröger, Harald. “Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis”. The Journal of Organic Chemistry 80.7 (2015): 3387-3396.
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PMID: 25710713
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