Enantioselective oxidation of prochiral 2-methyl-1,3-propandiol by Acetobacter pasteurianus

Molinari, Francesco; Gandolfi, Raffaella; Villa, Raffaella; Urban, E. J.; Kiener, Andreas

doi:10.1016/s0957-4166(03)00407-5

Cited by 41 publications

(26 citation statements)

References 6 publications

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“…[7][8][9] All reactions were 65 performed in aqueous media without using organic solvents, and separation and/or pre-treatment were not required due to high product yield in each step. The process provides significant environmental advantages over the acetone-cyanohydrin process used for methacrylic production, which is based on fossil gas or 70 oil as raw material, uses corrosive sulfuric acid and toxic HCN, and produces 1.5 tons of ammonium bisulfate as waste per ton of MMA.…”

Section: Discussionmentioning

confidence: 99%

“…7,16,17 The reaction was studied in 1 mL volume at varying substrate concentration (5, 7.5, 10 10, 12.5, 15, 20 and 30 g/L), pH 7.2 (0.1 M Tris-HCl), 29 °C using 2.6 mg of cell dry weight/mL. Substrate conversion, reaction rate and product formation were followed and are summarised in Table 1.…”

Section: Characterization Of Bioconversion and Reusability Of Cellsmentioning

confidence: 99%

“…7 2M1,3PD is a by-product of the butanediol production process involving hydroformylation reaction of allyl alcohol and CO/H 2 gas mixture in the presence of a catalyst, and hence is a cheap and commercially available 75 substrate. [7][8][9] Recently, the possibility of 2M1,3PD production…”

Section: Introductionmentioning

confidence: 99%

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A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

et al. 2012

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A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration Pyo, Sang-Hyun; Dishisha, Tarek; Dayankac, Secil; Gerelsaikhan, Jargalan; Lundmark, Stefan; Rehnberg, Nicola; Hatti-Kaul, Rajni Link to publication Citation for published version (APA): Pyo, S-H., Dishisha, T., Dayankac, S., Gerelsaikhan, J., Lundmark, S., Rehnberg, N., & Hatti-Kaul, R. (2012). A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration. Green Chemistry, 14(7), 1942-1948. DOI: 10.1039 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal Registered Charity Number 207890 Accepted ManuscriptThis is an Accepted Manuscript, which has been through the RSC Publishing peer review process and has been accepted for publication.Accepted Manuscripts are published online shortly after acceptance, which is prior to technical editing, formatting and proof reading. This free service from RSC Publishing allows authors to make their results available to the community, in citable form, before publication of the edited article. This Accepted Manuscript will be replaced by the edited and formatted Advance Article as soon as this is available.To cite this manuscript please use its permanent Digital Object Identifier (DOI®), which is identical for all formats of publication.More information about Accepted Manuscripts can be found in the Information for Authors.Please note that technical editing may introduce minor changes to the text and/or graphics contained in the manuscript submitted by the author(s) which may alter content, and that the standard Terms & Conditions and the ethical guidelines that apply to the journal are still applicable. In no event shall the RSC be held responsible for any errors or omissions in these Accepted Manuscript manuscripts or any consequences arising from the use of any information contained in them.www.rsc.org/greenchem 1463-9262(2010) Methacrylic acid was produced at high yield by an integrated process involving bioconversion of 2-methyl-1,3-propanediol (2M1,3PD) to 3-hydroxy-2-methylpropionic acid (3H2MPA) via 3-hydroxy-2-methylpropanal (3H2MPAL), and catalytic dehydration of the resulting acid. Whole cells of 10Gluconobacter oxydans grown on glycerol-based culture medium were used as catalyst for oxidative biotransformation that involved alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) enzymes in the organism....

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Section: Discussionmentioning

confidence: 99%

Section: Characterization Of Bioconversion and Reusability Of Cellsmentioning

confidence: 99%

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A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

et al. 2012

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“…16 Acetic acid bacteria are known to be particularly suited for carrying out these oxidations also on industrial scale. 17,18 In this work, we have investigated the oxidation of different polyunsaturated aldehydes and alcohols catalysed by Acetobacter aceti MIM2000/28, a microorganism already used for a number of selective bio-oxidations.…”

Section: Introductionmentioning

confidence: 99%

Direct conversion of polyconjugated compounds into their corresponding carboxylic acids by Acetobacter aceti

Pini¹,

Bertacche²,

Molinari³

et al. 2008

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“…Although 2-furoic acid, 5-hydroxymethyl-2-furancarboxylic acid and vanillic acid can be prepared from the corresponding aldehyde by some chemical oxidation methods, there are problems to be solved with respect to waste treatment, selectivity or productivity. Recently, various oxidations of alcohols and aldehydes with Acetobacter (Fu¨chtenbusch et al 1998, Wandel et al 2001, Molinari et al 2003, Gluconobacter (Molinari et al 1999), Nocardia (Pe´rez et al 1999) and Burkholderia (Tanaka & Hirokane 2000) strains have been reported. Therefore, we have attempted to introduce a bacterial oxidation process for the conversion of the renewable aldehydes to corresponding useful carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids by Acetobacter and Serratia strains

et al. 2004

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Conversion of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids was carried out using Acetobacter rancens IFO3297, A. pasteurianus IFO13753 and Serratia liquefaciens LF14. IFO3297 produced 110 g 2-furoic acid l(-1) from furfural with a 95% molar yield. 5-Hydroxymethyl-2-furancarboxylic acid was produced from the corresponding aldehyde by using whole cells LF14. IFO13753 and LF14 both converted isophthalaldehyde, 2,5-furandicarbaldehyde, 2,5-thiophenedicarbaldehyde and 2,2' biphenyldicarbaldehyde to the corresponding formylcarboxylic acid with 86-91% molar yields.

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Enantioselective oxidation of prochiral 2-methyl-1,3-propandiol by Acetobacter pasteurianus

Cited by 41 publications

References 6 publications

A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

Direct conversion of polyconjugated compounds into their corresponding carboxylic acids by Acetobacter aceti

Oxidation of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids by Acetobacter and Serratia strains

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