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Microbial production of D-(S)-chlorolactic acid by Proteus vulgaris cells

Andersson, Mats LU ; Holmberg, Hans LU and Adlercreutz, Patrick LU orcid (1998) In Enzyme and Microbial Technology 22(3). p.170-178
Abstract

Hydroxy carboxylate viologen oxidoreductase (HVOR) contained in Proteus vulgaris cells was used in the reduction of chloropyruvic acid to D-(S)-chlorolactic acid. A synthetic electron mediator 1,1'-carbamoylmethylviologen (CAV) was used to transfer electrons to HVOR. Three different methods for regenerating the mediator were evaluated: (1) electrochemically driven reduction; (2) reduction driven by formate using formate dehydrogenase; and (3) reduction driven by hydrogen gas using hydrogenase. On a small scale, all three methods provided yields of D-(S)-chlorolactic acid of around 80%. For gram-scale conversions, the method using formate dehydrogenase and formate appeared best. It was found beneficial to add... (More)

Hydroxy carboxylate viologen oxidoreductase (HVOR) contained in Proteus vulgaris cells was used in the reduction of chloropyruvic acid to D-(S)-chlorolactic acid. A synthetic electron mediator 1,1'-carbamoylmethylviologen (CAV) was used to transfer electrons to HVOR. Three different methods for regenerating the mediator were evaluated: (1) electrochemically driven reduction; (2) reduction driven by formate using formate dehydrogenase; and (3) reduction driven by hydrogen gas using hydrogenase. On a small scale, all three methods provided yields of D-(S)-chlorolactic acid of around 80%. For gram-scale conversions, the method using formate dehydrogenase and formate appeared best. It was found beneficial to add the chloropyruvic acid continuously during the reaction so as to avoid side reactions. Using 2.8 mg ml -1 of P. vulgaris cells, 4.4 mM CAV and a reaction time of 14 h, a preparative yield of 81% (6.6 mmol) of D-(S)-chlorolactic acid (ee > 97%) was obtained.

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type
Contribution to journal
publication status
published
subject
keywords
Artificial electron mediator, D-(S)-chlorolactic acid, Mediator regeneration, Proteus vulgaris
in
Enzyme and Microbial Technology
volume
22
issue
3
pages
9 pages
publisher
Elsevier
external identifiers
  • scopus:0032520227
ISSN
0141-0229
DOI
10.1016/S0141-0229(97)00152-X
language
English
LU publication?
yes
id
e9255473-f055-48f5-9e86-a52003d392ee
date added to LUP
2019-06-20 16:05:58
date last changed
2022-01-31 22:13:25
@article{e9255473-f055-48f5-9e86-a52003d392ee,
  abstract     = {{<p>                            Hydroxy carboxylate viologen oxidoreductase (HVOR) contained in Proteus vulgaris cells was used in the reduction of chloropyruvic acid to D-(S)-chlorolactic acid. A synthetic electron mediator 1,1'-carbamoylmethylviologen (CAV) was used to transfer electrons to HVOR. Three different methods for regenerating the mediator were evaluated: (1) electrochemically driven reduction; (2) reduction driven by formate using formate dehydrogenase; and (3) reduction driven by hydrogen gas using hydrogenase. On a small scale, all three methods provided yields of D-(S)-chlorolactic acid of around 80%. For gram-scale conversions, the method using formate dehydrogenase and formate appeared best. It was found beneficial to add the chloropyruvic acid continuously during the reaction so as to avoid side reactions. Using 2.8 mg ml                            <sup>-1</sup>                             of P. vulgaris cells, 4.4 mM CAV and a reaction time of 14 h, a preparative yield of 81% (6.6 mmol) of D-(S)-chlorolactic acid (ee &gt; 97%) was obtained.                        </p>}},
  author       = {{Andersson, Mats and Holmberg, Hans and Adlercreutz, Patrick}},
  issn         = {{0141-0229}},
  keywords     = {{Artificial electron mediator; D-(S)-chlorolactic acid; Mediator regeneration; Proteus vulgaris}},
  language     = {{eng}},
  month        = {{02}},
  number       = {{3}},
  pages        = {{170--178}},
  publisher    = {{Elsevier}},
  series       = {{Enzyme and Microbial Technology}},
  title        = {{Microbial production of D-(S)-chlorolactic acid by Proteus vulgaris cells}},
  url          = {{http://dx.doi.org/10.1016/S0141-0229(97)00152-X}},
  doi          = {{10.1016/S0141-0229(97)00152-X}},
  volume       = {{22}},
  year         = {{1998}},
}