Benzene-free synthesis of adipic acid

Wei Niu, K. M. Draths, J. W. Frost

Research output: Contribution to journalArticle

200 Citations (Scopus)

Abstract

Strains of Escherichia coli were constructed and evaluated that synthesized cis, cis-muconic acid from D-glucose under fed-batch fermentor conditions. Chemical hydrogenation of the cis, cis-muconic acid in the resulting fermentation broth has also been examined. Biocatalytic synthesis of adipic acid from glucose eliminates two environmental concerns characteristic of industrial adipic acid manufacture: use of carcinogenic benzene and benzene-derived chemicals as feedstocks and generation of nitrous oxide as a byproduct of a nitric acid catalyzed oxidation. While alternative catalytic syntheses that eliminate the use of nitric acid have been developed, most continue to rely on petroleum-derived benzene as the ultimate feedstock. In this study, E. coli WN1/pWN2.248 was developed that synthesized 36.8 g/L of cis, cis-muconic acid in 22% (mol/mol) yield from glucose after 48 h of culturing under fed-batch fermentor conditions. Optimization of microbial cis, cis-muconic acid synthesis required expression of three enzymes not typically found in E. coli. Two copies of the Klebsiella pneumoniae aroZ gene encoding DHS dehydratase were inserted into the E. coli chromosome, while the K. pneumoniae aroY gene encoding PCA decarboxylase and the Acinetobacter calcoaceticus catA gene encoding catechol 1,2-dioxygenase were expressed from an extrachromosomal plasmid. After fed-batch culturing of WN1/pWN2.248 was complete, the cells were removed from the broth, which was treated with activated charcoal and subsequently filtered to remove soluble protein. Hydrogenation of the resulting solution with 10% Pt on carbon (5% mol/mol) at 3400 kPa of H2 pressure for 2.5 h at ambient temperature afforded a 97% (mol/mol) conversion of cis, cis-muconic acid into adipic acid.

Original languageEnglish (US)
Pages (from-to)201-211
Number of pages11
JournalBiotechnology Progress
Volume18
Issue number2
DOIs
StatePublished - Jan 1 2002

Fingerprint

NSC 153174
Benzene
Escherichia coli
Nitric Acid
Hydrogenation
Klebsiella pneumoniae
Bioreactors
Glucose
Catechol 1,2-Dioxygenase
Acinetobacter calcoaceticus
Hydro-Lyases
Genes
Passive Cutaneous Anaphylaxis
Carboxy-Lyases
Charcoal
Petroleum
Nitrous Oxide
Fermentation
Plasmids
Carbon

ASJC Scopus subject areas

  • Biotechnology

Cite this

Benzene-free synthesis of adipic acid. / Niu, Wei; Draths, K. M.; Frost, J. W.

In: Biotechnology Progress, Vol. 18, No. 2, 01.01.2002, p. 201-211.

Research output: Contribution to journalArticle

Niu, W, Draths, KM & Frost, JW 2002, 'Benzene-free synthesis of adipic acid', Biotechnology Progress, vol. 18, no. 2, pp. 201-211. https://doi.org/10.1021/bp010179x
Niu, Wei ; Draths, K. M. ; Frost, J. W. / Benzene-free synthesis of adipic acid. In: Biotechnology Progress. 2002 ; Vol. 18, No. 2. pp. 201-211.
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