Enantioselective microbial reduction of substituted acetophenones

Patel, Ramesh N.; Goswami, Animesh; Chu, Linda; Donovan, Mary Jo; Nanduri, Venkata; Goldberg, Steven L.; Johnston, Robert M.; Siva, P.; Nielsen, Brent L.; Fan, Junying; He, WeiXuan; Shi, Zugui; Wang, Kwok Y; Eiring, R F; Cazzulino, Dana; Singh, Ambarish K.; Mueller, Richard H.

doi:10.1016/j.tetasy.2004.02.024

Cited by 69 publications

(40 citation statements)

References 21 publications

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“…Therefore, a regeneration of the reduced cofactor is necessary by either a second substrate or a second enzyme together with a second substrate (Chenault and Whitesides, 1987;Geueke et al, 2003;Hummel, 1999;Weckbecker et al, 2010). To overcome the problem of cofactor regeneration and to improve and simplify the process, a simultaneous expression of two or more enzymes in a single cell is a promising approach, which has been shown by numerous literature known processes using whole-cell catalyst (Goldberg et al, 2007;Gröger et al, 2004Gröger et al, , 2006aKataoka et al, 1999;Kosjek et al, 2008;Patel et al, 2004;Schroer et al, 2007;Uzura et al, 2009;Weckbecker and Hummel, 2004).…”

Section: Introductionmentioning

confidence: 99%

Characterization of a whole‐cell catalyst co‐expressing glycerol dehydrogenase and glucose dehydrogenase and its application in the synthesis of L‐glyceraldehyde

Richter¹,

Neumann²,

Liese³

et al. 2010

Biotech & Bioengineering

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A whole-cell catalyst using Escherichia coli BL21(DE3) as a host, co-expressing glycerol dehydrogenase (GlyDH) from Gluconobacter oxydans and glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration, has been successfully constructed and used for the reduction of aliphatic aldehydes, such as hexanal or glyceraldehyde to the corresponding alcohols. This catalyst was characterized in terms of growth conditions, temperature and pH dependency, and regarding the influence of external cofactor and permeabilization. In the case of external cofactor addition we found a 4.6-fold increase in reaction rate caused by the addition of 1 mM NADP(+). Due to the fact that pH and temperature are also factors which may affect the reaction rate, their effect on the whole-cell catalyst was studied as well. Comparative studies between the whole-cell catalyst and the cell-free system were investigated. Furthermore, the successful application of the whole-cell catalyst in repetitive batch conversions could be demonstrated in the present study. Since the GlyDH was recently characterized and successfully applied in the kinetic resolution of racemic glyceraldehyde, we were now able to transfer and establish the process to a whole-cell system, which facilitated the access to L-glyceraldehyde in high enantioselectivity at 54% conversion. All in all, the whole-cell catalyst shows several advantages over the cell-free system like a higher thermal, a similar operational stability and the ability to recycle the catalyst without any loss-of-activity. The results obtained making the described whole-cell catalyst an improved catalyst for a more efficient production of enantiopure L-glyceraldehyde.

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Section: Introductionmentioning

confidence: 99%

Characterization of a whole‐cell catalyst co‐expressing glycerol dehydrogenase and glucose dehydrogenase and its application in the synthesis of L‐glyceraldehyde

Richter¹,

Neumann²,

Liese³

et al. 2010

Biotech & Bioengineering

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“…The studies on yeasts have shown that they transfer the pro-R-hydride to the re-face of the carbonyl group to give (S)-alcohols, a process described by Prelog's rule (Faber, 1997). To our knowledge, this is the fi rst report on obtaining of (R)-1-phenylethanol by yeast reduction of 1 at higher conversion and enantiomeric excess, without the use of additive substances (Patel et al, 2004;Zymanczyk-Duda et al, 2005).…”

Section: Reduction Of Acetophenone (1)mentioning

confidence: 87%

Bioreduction of Some Common Carbonylic Compounds Mediated by Yeasts

Silva

Alarcón

Águila

et al. 2010

Zeitschrift Für Naturforschung C

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Bioreduction of several prochiral carbonylic compounds such as acetophenone (1), ethyl acetoacetate (2) and ethyl phenylpropionate (3) to the corresponding optically active secalcohols 1a -3a was performed using wild-type strains of Pichia pastoris UBB 1500, Rhodotorula sp., and Saccharomyces cerevisiae. The reductions showed moderate to excellent conversion and high enantiomeric excess, in an extremely mild and environmentally benign manner in aqueous medium, using glucose as cofactor regeneration system. The obtained alcohols follow Prelog's rule, but in the reduction of 1 with P. pastoris UBB 1500 the antiPrelog enantiopreference was observed.

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“…The reaction was optimized and carried out on a kilogram scale to provide the S-alcohol 130 in 65% isolated yield and >99% e.e. [62]. …”

Section: B Reduction Of Ketones To Alcoholsmentioning

confidence: 99%