Production of l-phenylacetylcarbinol by fermentation

Tripathi, Chandrakant Mani; Agarwal, Shikha; Basu, S. K.

doi:10.1016/s0922-338x(97)81900-9

Cited by 33 publications

(23 citation statements)

References 28 publications

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“…Two well-known enzymes in this category are pyruvate decarboxylase (PDC) and 2-ketoisovalerate decarboxylase (KivD). The native role of PDCs is to convert pyruvate to acetaldehyde, but their promiscuity and capability of catalyzing carboligation side reactions have led to their use in synthesis of chiral carboligation products (12). KivD is also promiscuous and has been utilized for synthesis of numerous nonnatural alcohols derived from amino acid intermediates (35).…”

Section: Engineering Aldehyde Biosynthetic Reactions and Pathwaysmentioning

confidence: 99%

“…In our report on aromatic aldehyde accumulation (43), we demonstrated this potential by using the RARE strain to produce L-phenylacetylcarbinol (L-PAC), a chiral precursor to the pharmaceutical ephedrine (12)(13)(14)(15). Although whole-cell catalysts have been used for L-PAC synthesis for a long time, significant benzyl alcohol byproduct formation occurs from their use, resulting in low yields (12). Cultures of the RARE strain expressing a recombinant mutant PDC were able to produce L-PAC using exogenously supplied benzaldehyde and metabolized pyruvate with minimal benzyl alcohol formation.…”

Section: Enhancing Bioconversion Of Aldehydes To Other Chemical Classesmentioning

confidence: 99%

“…Certain aldehydes, such as trans-2-hexenal, phenylacetaldehyde, and nonanal, evoke responses in insects by serving as pheromones or attractants (9)(10)(11). The high reactivity of the carbonyl group of aldehydes enables many industrial uses beyond flavors and fragrances, such as precursors to pharmaceuticals (12)(13)(14)(15). However, the high reactivity of aldehydes also contributes to their increased toxicity in microorganisms.…”

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confidence: 99%

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Microbial Engineering for Aldehyde Synthesis

Kunjapur

Prather

2015

Appl Environ Microbiol

149

129

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Aldehydes are a class of chemicals with many industrial uses. Several aldehydes are responsible for flavors and fragrances present in plants, but aldehydes are not known to accumulate in most natural microorganisms. In many cases, microbial production of aldehydes presents an attractive alternative to extraction from plants or chemical synthesis. During the past 2 decades, a variety of aldehyde biosynthetic enzymes have undergone detailed characterization. Although metabolic pathways that result in alcohol synthesis via aldehyde intermediates were long known, only recent investigations in model microbes such as Escherichia coli have succeeded in minimizing the rapid endogenous conversion of aldehydes into their corresponding alcohols. Such efforts have provided a foundation for microbial aldehyde synthesis and broader utilization of aldehydes as intermediates for other synthetically challenging biochemical classes. However, aldehyde toxicity imposes a practical limit on achievable aldehyde titers and remains an issue of academic and commercial interest. In this minireview, we summarize published efforts of microbial engineering for aldehyde synthesis, with an emphasis on de novo synthesis, engineered aldehyde accumulation in E. coli, and the challenge of aldehyde toxicity.

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Section: Engineering Aldehyde Biosynthetic Reactions and Pathwaysmentioning

confidence: 99%

Section: Enhancing Bioconversion Of Aldehydes To Other Chemical Classesmentioning

confidence: 99%

mentioning

confidence: 99%

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Microbial Engineering for Aldehyde Synthesis

Kunjapur

Prather

2015

Appl Environ Microbiol

149

129

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“…Typical R-PAC levels reported in the literature for its fermentative production are 10-15 g/L (Shin and Rogers, 1995;Tripathi et al, 1997). A novel organic-aqueous phase enzyme based R-PAC production method using partially purified PDC from C. utilis has been developed by our group with R-PAC levels of more than 100 g/L in the organic phase (Rosche et al, 2002b;Sandford et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

pH shift enhancement ofCandida utilis pyruvate decarboxylase production

Chen

Breuer

Hauer

et al. 2005

Biotechnol. Bioeng.

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Pyruvate decarboxylase (PDC) catalyses the synthesis of asymmetric carbinols, e.g., chiral precursors for pharmaceuticals such as ephedrine and pseudoephedrine. The production of PDC by Candida utilis in a minimal medium was improved by manipulating the pH during fermentation in a 5 L bioreactor. At an aeration rate of 0.1 vvm with a stirrer speed of 300 rpm at constant pH 6, a specific PDC activity of 141 U/g dry cell weight (DCW) was achieved (average of two fermentations +/-13%). By allowing the yeast to acidify the growth medium from pH 6 to 2.9, the final specific PDC activity increased by a factor of 2.7 to 385 U/g DCW (average from 4 fermentations +/-16%). The effect of this pH drift on PDC production was confirmed by another experiment with a manual shift of pH from 6 to 3 by addition of 5 M sulfuric acid. The final PDC activity was 392 U/g DCW (average from two fermentations +/-5%). However, experiments with constant pH of 6, 5, 4, or 3 resulted in average specific activities of only 102 to 141 U/g DCW, suggesting that a transitional pH change rather than the absolute pH value was responsible for the increased specific PDC activity.

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“…Furthermore, the fact that the 2-hydroxy carbonyl structural unit is found in sugars, terpenes and antibiotics makes 2-hydroxy ketones important precursors in the synthesis of natural products and pharmaceuticals (Hannessian, 1983) such as the antifungal Sch42427 (Gala et al, 1996;Konosu et al, 1991) or L-ephedrine (Rogers et al, 1997;Shin and Rogers, 1995;Tripathi et al, 1997).…”

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confidence: 99%

The production of (R)‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

Hildebrand

Kühl

Pohl

et al. 2006

Biotech & Bioengineering

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Benzaldehyde lyase (BAL; E.C. 4.1.2.38) from Pseudomonas fluorescens Biovar I catalyzes the reversible formation of benzoins from aromatic aldehydes, and, moreover, the coupling of aromatic with aliphatic aldehydes yielding derivatives of (R)-2-hydroxy-1-phenyl- propan-1-one (R)-HPPs), which are important chiral building blocks. In this paper, we report on the development of a reactor system that allows the selective production of substituted (R)-HPP-derivatives. The reaction systems yielding (R)-1-(3-chloro-phenyl)-2-hydroxy- propan-1-one, (R)-2-hydroxy-3-methoxy-1-(4-methoxy-phenyl)-propan-1-one, and (R)-2-hydroxy-3,3-dimethoxy-1-phenyl-propan-1-one were investigated. A kinetic model optimized by batch experiments was developed, for the description of both batch and continuously operated reactors. This model was used to describe the HPP production in a continuously operated enzyme membrane reactor. The reactor type used combines the advantages of high conversion and excellent selectivity with high space-time yields and total turnover numbers of up to ttn=43,000. Products were obtained in high yield on a gram scale.

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Production of l-phenylacetylcarbinol by fermentation

Cited by 33 publications

References 28 publications

Microbial Engineering for Aldehyde Synthesis

Microbial Engineering for Aldehyde Synthesis

pH shift enhancement ofCandida utilis pyruvate decarboxylase production

The production of (R)‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

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