Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30)

Yildirim, Selçuk; Zezula, Josef; Hudlicky, Tomas; Witholt, Bernard; Schmid, Andreas

doi:10.1002/adsc.200404032

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30)
Authors:	Yildirim, Selçuk Zezula, Josef Hudlicky, Tomas Witholt, Bernard Schmid, Andreas
DOI:	10.1002/adsc.200404032
Published in:	Advanced Synthesis & Catalysis
Volume(Issue):	346
Issue:	8
Page(s):	933
Pages to:	942
Issue Date:	Aug-2004
Publisher / Ed. Institution:	Wiley
ISSN:	1615-4150 1615-4169
Language:	English
Subject (DDC):	660.6: Biotechnology
Abstract:	Asymmetric cis‐dihydroxylations of aromatic compounds are catalyzed by bacterial dioxygenases. In order to prevent through conversion, either dihydrodiol dehydrogenase blocked mutant strains or recombinant bacterial cells are used as biocatalysts for synthetic purposes. We characterized the cis‐dihydroxylation of cinnamonitrile by chlorobenzene dioxygenase (CDO) in recombinant E. coli on different reaction scales. The absolute stereochemistry of the product was determined to be trans‐3‐[(5S,6R)‐5,6‐dihydroxycyclohexa‐1,3‐dienyl]‐acrylonitrile. The cells showed a maximum specific activity of 3.76 U/g cdw in shake‐flask experiments. Stable expression of the dioxygenase genes in E. coli JM101 (pTEZ30) resulted in increasing volumetric productivities. The maximum volumetric productivities of 80 and 92 mg product/L/h were achieved on 2‐L and 30‐L scales, respectively. The specific growth rate correlated with the volumetric productivity during the biotransformations. An average volumetric productivity of 40 mg product/L/h in reactors on 2‐L and 30‐L scales resulted in 0.96 and 16.4 g of isolated product at the end of the biotransformations. This points out the need for metabolically active cells and controllable expression systems for achieving high volumetric productivities for cofactor dependent biooxidations. We have now applied this concept for the asymmetric dihydroxylation of the non‐natural substrate cinnamonitrile using multicomponent CDO in tailored E. coli JM101 in long‐term reactions.
URI:	https://digitalcollection.zhaw.ch/handle/11475/7592
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Organisational Unit:	Institute of Food and Beverage Innovation (ILGI)
Appears in collections:	Publikationen Life Sciences und Facility Management

Files in This Item:

There are no files associated with this item.

Show full item record

Yildirim, S., Zezula, J., Hudlicky, T., Witholt, B., & Schmid, A. (2004). Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30). Advanced Synthesis & Catalysis, 346(8), 933–942. https://doi.org/10.1002/adsc.200404032

Yildirim, S. et al. (2004) ‘Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30)’, Advanced Synthesis & Catalysis, 346(8), pp. 933–942. Available at: https://doi.org/10.1002/adsc.200404032.

S. Yildirim, J. Zezula, T. Hudlicky, B. Witholt, and A. Schmid, “Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30),” Advanced Synthesis & Catalysis, vol. 346, no. 8, pp. 933–942, Aug. 2004, doi: 10.1002/adsc.200404032.

YILDIRIM, Selçuk, Josef ZEZULA, Tomas HUDLICKY, Bernard WITHOLT und Andreas SCHMID, 2004. Asymmetric dihydroxylation of cinnamonitrile totrans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile using chlorobenzene dioxygenase in Escherichia coli (pTEZ30). Advanced Synthesis & Catalysis. August 2004. Bd. 346, Nr. 8, S. 933–942. DOI 10.1002/adsc.200404032

Yildirim, Selçuk, Josef Zezula, Tomas Hudlicky, Bernard Witholt, and Andreas Schmid. 2004. “Asymmetric Dihydroxylation of Cinnamonitrile Totrans-3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-Dienyl]-Acrylonitrile Using Chlorobenzene Dioxygenase in Escherichia Coli (pTEZ30).” Advanced Synthesis & Catalysis 346 (8): 933–42. https://doi.org/10.1002/adsc.200404032.

Yildirim, Selçuk, et al. “Asymmetric Dihydroxylation of Cinnamonitrile Totrans-3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-Dienyl]-Acrylonitrile Using Chlorobenzene Dioxygenase in Escherichia Coli (pTEZ30).” Advanced Synthesis & Catalysis, vol. 346, no. 8, Aug. 2004, pp. 933–42, https://doi.org/10.1002/adsc.200404032.