Utilization of Aliphatic Hydrocarbons by Micro-organisms

Klug, Michael J.; Markovetz, A. J.

doi:10.1016/s0065-2911(08)60404-x

Cited by 149 publications

(63 citation statements)

References 131 publications

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“…These enzymes require a reduced co factor for catalysis, and incorporate molecular oxygen directly into organic molecules and do so with a very high efficiency and selectivity. Microorganisms attack a wide range of saturated and unsaturated hydrocarbons (Klug & Markovetz, 1971) and are able to form epoxides from alkenes, arenes and halohydrins by different enzymatic epoxidation reactions ( fig. 1).…”

Section: Microbial Epoxidation Of Olefinsmentioning

confidence: 99%

“…(Klug & Markovetz, 1971). Most of these organisms grow well on ethane, propane or butane (Philips & Perry, 1974;Hou etal, 1983; P atella/., 1983).…”

Section: Alkane-utilizersmentioning

confidence: 99%

“…Most of these organisms grow well on ethane, propane or butane (Philips & Perry, 1974;Hou etal, 1983; P atella/., 1983). In general, the pathway of alkane degradation proceeds via terminal hydroxylation of the alkane, yielding the corresponding primary alcohol (Klug & Markovetz, 1971) but subterminal oxidations have also been demonstrated (Vestal & Perry, 1969).…”

Section: Alkane-utilizersmentioning

confidence: 99%

“…Two approaches were undertaken: i) screening for the ability to grow on 'simple' (ethene, propene) olefins on the premise that the enzyme(s) might not be highly substrate specific and ii) screening for organisms that grow on a series of 'blocked' (table 6) olefins. The latter approach was based upon the observation that although primary aliphatic carbons are more readily attacked (in nature) than olefins (Klug & Markovetz, 1971), steric hindrance (e.g. with secondary and tertiary carbons) mightreverse this preference, making the attack at the double bond more likely.…”

Section: Applications Of Epoxidation Reactions In Biotechnological Prmentioning

confidence: 99%

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Biocatalysts for production of chiral epoxides

Mahmoudian

Michael

1992

Appl Microbiol Biotechnol

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An extensive screen for microorganisms capable of growth on olefins was carried out. Over 100 bacterial strains (mesophilic, thermophilic) were isolated in pure culture with gaseous or liquid (internal & terminal) olefins as the sole source of carbon and energy. The organisms included Aero coccus, Aeromonas,Alcaligenes, Flavobacterium, Micrococcus, Moraxella, Nocardia, Pseudomonas, Staphylococcus, Streptomyces and Vibrio spp. and a variety of Gram-negative, Gram-positive and Gram-variable rods/coccobacilli not yet identified. Given the success of isolating many different genera of alkene-utilizing bacteria, it would suggest that the ability to utilize olefin hydrocarbons is more widespread in nature than previously recognized.Initial studies involved testing a collection of strains for i) growth rate on the substrate of isolation and ii) evidence of epoxide accumulation from lower gaseous olefins. All of the 18 ethene-and propene-utilizing bacteria tested, stereospecifically formed R-1,2-epoxypropane (ee=90-96%), R -l,2-epoxybutane (ee=90-98%) and trans-(2/?,37?)-epoxybutane (ee=64-88%), as analyzed by chiral complexation glc. A particularly promising strain of Micrococcus sp. M90C was selected to demonstrate: a) Induction of epoxidation activity in carbohydrate-grown cells. b) Optimization of a biotransformation process for production of epoxyethane. c) Involvement of a specific monooxygenase in the formation of chiral epoxides. d) Stereoselectivity of epoxyalkane degradation. e) Substrate specificity toward a range of olefins.Micrococcus sp. M90C stereospecifically formed S-(+)-phenyl glycidyl ether (ee=93%) and /?-(+)-phenyl methyl sulphoxide (ee>98%), as analyzed by chiral-shift NMR and HPLC. The ability to catalyze heteroatom oxygenation as well as epoxidation of a wide range of olefins in high optical and chemical yields, demonstrates its potential as a 'general-purpose' biocatalyst for the production of optically pure oxygenated compounds.Two other promising ethene-utilizing bacteria (M26, M93 A) each catalyzed the stereospecific formation of S-(+)-phenyl glycidyl ether (ee=93%). This has attracted considerable industrial interest and is currently under investigation at ICI for commercial production of optically active./1-blockers. In addition to Micrococcus sp. M90C, the substrate specificities of 6 other organisms were studied in order to probe the active site of the enzymes involved. The pattern of reactivity for the group of 4 ethene-(M26, M90C, M93A, M186) and 2 propene-(M142, M l 56) utilizers differed from that expected with peracids, suggesting a considerable degree of enzymatic control.The nature of the substrate, however, modulated enzymatic epoxidations in Staphylcoccus sp. M97B. CONTENTS

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Section: Microbial Epoxidation Of Olefinsmentioning

confidence: 99%

“…(Klug & Markovetz, 1971). Most of these organisms grow well on ethane, propane or butane (Philips & Perry, 1974;Hou etal, 1983; P atella/., 1983).…”

Section: Alkane-utilizersmentioning

confidence: 99%

Section: Alkane-utilizersmentioning

confidence: 99%

Section: Applications Of Epoxidation Reactions In Biotechnological Prmentioning

confidence: 99%

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Biocatalysts for production of chiral epoxides

Mahmoudian

Michael

1992

Appl Microbiol Biotechnol

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“…Alkanes are one of the most hydrophobic compounds among substrates of P450s. Alkanes are widespread high energy carbon resources, and many microorganisms, including bacteria, yeasts, and fungi, have developed metabolic systems to utilize those compounds (2,3). P450s are employed for initial terminal hydroxylation of alkanes in some alkaneutilizing prokaryotic (4) and eukaryotic microorganisms (5).…”

mentioning

confidence: 99%

A Basic Helix-Loop-Helix Transcription Factor Essential for Cytochrome P450 Induction in Response to Alkanes in Yeast Yarrowia lipolytica

Yamagami

Morioka

Fukuda

et al. 2004

Journal of Biological Chemistry

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When the alkane-assimilating yeast Yarrowia lipolytica is cultivated on n-alkanes, it changes cellular metabolism for adaptation by inducing cytochrome P450 and other genes. From a comparative analysis of promoters of alkane-inducible genes, we identified a cisacting element, ARE1 (alkane responsive element 1), which provides transcription induction in response to n-alkanes. In a genetic selection for mutants that were defective in ARE1-mediated transcription induction in the presence of n-alkanes, we found that the YAS1 (yeast alkane signaling) gene is essential for alkane response. The YAS1 gene encodes a basic helix-loop-helix (bHLH) family protein. Loss of Yas1p causes defects in n-alkanedependent transcription induction of the P450 gene and growth on n-alkanes. Yas1p localizes to nuclei and binds to promoters containing ARE1. Yas1p also binds to its own promoter, and the expression of YAS1 is induced by n-alkanes. These features suggest that Yas1p is a novel transcription factor mediating alkane signaling and that it provides an autoregulatory loop.

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