TY - JOUR

T1 - Adsorbent-Based Downstream-Processing of the Decarboxylase-Based Synthesis of 2,6-Dihydroxy-4-methylbenzoic Acid

AU - Meyer, Lars-Erik

AU - Plasch, Katharina

AU - Kragl, Udo

AU - Von Langermann, Jan

N1 - Funding information: The authors thank the entire research group of Prof. Dr. Hubert Bahl (Department of Microbiology, University of Rostock) for their ongoing support and useful discussions. The authors also thank Marek Biermann and Lukas Friederici for their assistance in the experimental work. Financial support is gratefully acknowledged by the DFG (Deutsche Forschungsgemeinschaft), Grant Number 252186816, and FWF (Fonds zur Förderung der wissenschaft-lichen Forschung), Grant Number 1637 (ERA; ERA Chemistry Open Call 6; ERA Chemistry Open Initiative). Notes The authors declare no competing financial interest.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - In this case study the regioselective enzymatic carboxylation of 3,5-dihydroxytoluene (orcinol) using the nonoxidative 2,3-dihydroxybenzoic acid decarboxylase from Aspergillus oryzae (2,3-DHBD-Ao), followed by an adsorbent-based downstream approach, has been investigated. The product 2,6-dihydroxy-4-methylbenzoic acid (DHMBA) was herein purified by an adsorption-desorption cycle and subsequently obtained with purities >99% without a full elimination of the excess bicarbonate from its reaction solution. Ten adsorbent resins were studied in respect of their ability to recover the product from the reaction solution, whereas the strong anion exchange resin Dowex 1x2 in its chloride form showed affinities >99%, even at bicarbonate concentrations of >3 mol·L-1. Desorption from loaded resin was carried out by a 2 mol·L-1 HCl/acetone mixture, followed by product crystallization during acetone evaporation. This presented concept does not require a final column preparation step and improves the overall atom efficiency of the biocatalytic reaction system.

AB - In this case study the regioselective enzymatic carboxylation of 3,5-dihydroxytoluene (orcinol) using the nonoxidative 2,3-dihydroxybenzoic acid decarboxylase from Aspergillus oryzae (2,3-DHBD-Ao), followed by an adsorbent-based downstream approach, has been investigated. The product 2,6-dihydroxy-4-methylbenzoic acid (DHMBA) was herein purified by an adsorption-desorption cycle and subsequently obtained with purities >99% without a full elimination of the excess bicarbonate from its reaction solution. Ten adsorbent resins were studied in respect of their ability to recover the product from the reaction solution, whereas the strong anion exchange resin Dowex 1x2 in its chloride form showed affinities >99%, even at bicarbonate concentrations of >3 mol·L-1. Desorption from loaded resin was carried out by a 2 mol·L-1 HCl/acetone mixture, followed by product crystallization during acetone evaporation. This presented concept does not require a final column preparation step and improves the overall atom efficiency of the biocatalytic reaction system.

KW - biocatalysis

KW - carboxylation

KW - Downstream-processing (DSP)

KW - ion-exchange resin

KW - ortho-benzoic acid decarboxylases

UR - http://www.scopus.com/inward/record.url?scp=85049308828&partnerID=8YFLogxK

U2 - 10.1021/acs.oprd.8b00104

DO - 10.1021/acs.oprd.8b00104

M3 - Article

AN - SCOPUS:85049308828

VL - 22

SP - 963

EP - 970

JO - Organic Process Research and Development

JF - Organic Process Research and Development

SN - 1083-6160

IS - 8

ER -