Details
| Original language | English |
|---|---|
| Pages (from-to) | 85-93 |
| Number of pages | 9 |
| Journal | Organic Process Research and Development |
| Volume | 21 |
| Issue number | 1 |
| Early online date | 16 Dec 2016 |
| Publication status | Published - 20 Jan 2017 |
| Externally published | Yes |
Abstract
The transformation of (abundant) oxygenated biomass-derived building blocks via chemo-enzymatic methods is a valuable concept for accessing useful compounds, as it combines the high selectivity of enzymes and the versatility of chemical catalysts. In this work, we demonstrate a straightforward combination of a phenolic acid decarboxylase (PAD) and palladium on charcoal (Pd/C) that affords the flavor compound 4-ethylguaiacol from ferulic acid. The use of a two-phase system proved to be advantageous in terms of enzyme activity, stability, and volumetric productivity and allows us to carry out the hydrogenation step directly in the organic layer containing exclusively the intermediate, vinylguaiacol. The enzymatic decarboxylation step in the biphasic system afforded 89% conversion of 100 mM (19 g L-1) ferulic acid with an isolated yield of 75%. By extracting 4- vinylguaiacol continuously into the organic phase, conversion was enhanced to 92% using 170 mM (33 g L-1) ferulic acid, which was only possible in the continuous extraction and distillation setup developed. The reaction cascade (PAD-Pd/C) is demonstrated at gram scale, affording the target product 4-ethylguaiacol (1.1 g) in 70% isolated yield in a two-step two-pot process. The enzymatic step was characterized in detail to overcome major constraints, and the process favorably compares in terms of the environmental impact with traditional approaches.
Keywords
- Biocatalysis, Biphasic system, Chemical reduction, Chemo-enzymatic cascade, Decarboxylation
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Process Research and Development, Vol. 21, No. 1, 20.01.2017, p. 85-93.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Development and Scaling-Up of the Fragrance Compound 4‑Ethylguaiacol Synthesis via a Two-Step Chemo-Enzymatic Reaction Sequence
AU - Pesci, Lorenzo
AU - Baydar, Maik
AU - Glueck, Silvia
AU - Faber, Kurt
AU - Liese, Andreas
AU - Kara, Selin
PY - 2017/1/20
Y1 - 2017/1/20
N2 - The transformation of (abundant) oxygenated biomass-derived building blocks via chemo-enzymatic methods is a valuable concept for accessing useful compounds, as it combines the high selectivity of enzymes and the versatility of chemical catalysts. In this work, we demonstrate a straightforward combination of a phenolic acid decarboxylase (PAD) and palladium on charcoal (Pd/C) that affords the flavor compound 4-ethylguaiacol from ferulic acid. The use of a two-phase system proved to be advantageous in terms of enzyme activity, stability, and volumetric productivity and allows us to carry out the hydrogenation step directly in the organic layer containing exclusively the intermediate, vinylguaiacol. The enzymatic decarboxylation step in the biphasic system afforded 89% conversion of 100 mM (19 g L-1) ferulic acid with an isolated yield of 75%. By extracting 4- vinylguaiacol continuously into the organic phase, conversion was enhanced to 92% using 170 mM (33 g L-1) ferulic acid, which was only possible in the continuous extraction and distillation setup developed. The reaction cascade (PAD-Pd/C) is demonstrated at gram scale, affording the target product 4-ethylguaiacol (1.1 g) in 70% isolated yield in a two-step two-pot process. The enzymatic step was characterized in detail to overcome major constraints, and the process favorably compares in terms of the environmental impact with traditional approaches.
AB - The transformation of (abundant) oxygenated biomass-derived building blocks via chemo-enzymatic methods is a valuable concept for accessing useful compounds, as it combines the high selectivity of enzymes and the versatility of chemical catalysts. In this work, we demonstrate a straightforward combination of a phenolic acid decarboxylase (PAD) and palladium on charcoal (Pd/C) that affords the flavor compound 4-ethylguaiacol from ferulic acid. The use of a two-phase system proved to be advantageous in terms of enzyme activity, stability, and volumetric productivity and allows us to carry out the hydrogenation step directly in the organic layer containing exclusively the intermediate, vinylguaiacol. The enzymatic decarboxylation step in the biphasic system afforded 89% conversion of 100 mM (19 g L-1) ferulic acid with an isolated yield of 75%. By extracting 4- vinylguaiacol continuously into the organic phase, conversion was enhanced to 92% using 170 mM (33 g L-1) ferulic acid, which was only possible in the continuous extraction and distillation setup developed. The reaction cascade (PAD-Pd/C) is demonstrated at gram scale, affording the target product 4-ethylguaiacol (1.1 g) in 70% isolated yield in a two-step two-pot process. The enzymatic step was characterized in detail to overcome major constraints, and the process favorably compares in terms of the environmental impact with traditional approaches.
KW - Biocatalysis
KW - Biphasic system
KW - Chemical reduction
KW - Chemo-enzymatic cascade
KW - Decarboxylation
UR - http://www.scopus.com/inward/record.url?scp=85035017155&partnerID=8YFLogxK
U2 - 10.1021/acs.oprd.6b00362
DO - 10.1021/acs.oprd.6b00362
M3 - Article
AN - SCOPUS:85035017155
VL - 21
SP - 85
EP - 93
JO - Organic Process Research and Development
JF - Organic Process Research and Development
SN - 1083-6160
IS - 1
ER -