Regiospecific Internal Desaturation of Aliphatic Compounds by a Mutant
            <i>Rhodococcus</i>
            Strain

Koike, Kenichi; Ara, Katsutoshi; Adachi, Shigehito; Takigawa, Hirofumi; Mori, Hajime; Inoue, Shintaro; Kimura, Yoshiharu; Ito, Susumu

doi:10.1128/aem.65.12.5636-5638.1999

Cited by 19 publications

(3 citation statements)

References 14 publications

(11 reference statements)

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“…These results suggest that sp. 008 uses hexadecane more e ciently than KSM B-3M through different metabolic pathways alluding that the mutation of the strain KSM B-3M potentially blocked subsequent alkane metabolism pathways 27 . To further identify the genes responsible for this transformation, we performed transcriptomic comparison between KSM B-3M and sp.…”

Section: Main Textmentioning

confidence: 99%

“…The selective and e cient desaturation of linear saturated unfunctionalized hydrocarbons into their corresponding unsaturated products was missing as alkenes were never directly assessed as catabolic intermediates in alkane biodegradation. Crucially, a mutant strain of Rhodococcus (Rhodococcus KSM-B-3M) [26][27][28] , obtained through random mutagenesis of the wild type strain Rhodococcus KSM-B-3, could hyperproduce internal alkenes from linear alkanes in rather low yields. We were therefore interested to implement this original low-yielding transformation as a general approach and evaluate whether synthetically useful yields of alkenes could be obtained.…”

Section: Main Textmentioning

confidence: 99%

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Selective Terminal Functionalization of Linear Alkanes

Marek

Bruffaerts

Buhnik-Rosenblau

et al. 2021

Preprint

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Selective undirected functionalization of strong primary C-H bonds of linear alkanes, that do not possess directing groups, historically stands as one of the most challenging transformation in chemistry. In this Article, we report a two-step sequential strategy involving a biocatalytic dehydrogenation / remote hydrofunctionalization, as a unified and versatile approach to selectively convert linear alkanes into a large array of valuable functionalized aliphatic derivatives. The dehydrogenation is carried out by a mutant strain of Rhodococcus and the produced alkenes are subsequently engaged in a remote functionalization through a metal-catalyzed hydrometalation/migration sequence that subsequently react with a large variety of electrophiles. The judicious implementation of this combined biocatalytic and organometallic approach enabled us to develop a high-yielding protocol to site-selectively functionalize unreactive primary C–H bonds.

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Section: Main Textmentioning

confidence: 99%

Section: Main Textmentioning

confidence: 99%

Selective Terminal Functionalization of Linear Alkanes

Marek

Bruffaerts

Buhnik-Rosenblau

et al. 2021

Preprint

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“…[39,40] The selective and efficient desaturation of linear saturated unfunctionalized hydrocarbons into their corresponding unsaturated products was missing as unfunctionalized alkenes were never directly assessed as catabolic intermediates in alkane biodegradation. Crucially, a mutant strain of the bacteria Rhodococcus (Rhodococcus KSM-B-3M), [41] obtained through random mutagenesis of the wild-type strain Rhodococcus KSM-B-3, was reported to hyperproduce internal alkenes from linear alkanes in a rather low yield (11 %). We were therefore interested to implement and improve this original low-yielding transformation as a general approach and evaluate whether synthetically useful yields of alkenes could be obtained.…”

mentioning

confidence: 99%

Selective Terminal Functionalization of Linear Alkanes**

et al. 2023

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A two‐step sequential strategy involving a biocatalytic dehydrogenation/remote hydrofunctionalization, as a unified and versatile approach to selectively convert linear alkanes into a large array of valuable functionalized aliphatic derivatives is reported. The dehydrogenation is carried out by a mutant strain of a bacteria Rhodococcus and the produced alkenes are subsequently engaged in a remote functionalization through a metal‐catalyzed hydrometalation/migration sequence that subsequently react with a large variety of electrophiles. The judicious implementation of this combined biocatalytic and organometallic approach enabled us to develop a high‐yielding protocol to site‐selectively functionalize unreactive primary C−H bonds.

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Bioremediation

Ward¹

2010

Encyclopedia of Industrial Biotechnology

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Bioremediation, which exploits biological processes to remove contaminants from the biosphere, is generally a low‐cost option among remediation alternatives. The organisms involved are predominantly microbes which have the capacity to survive contaminant toxicity and access and transform the contaminants. Many contaminants are organic solvents which disrupt membranes, and cells may develop defence mechanisms including formation of outer cell‐membrane‐protective material, often hydrophobic or solvent efflux pumps. Many of the contaminants are hydrophobic and microbial species appear to take up these substances by a combination of biosurfactant secretion and direct cell‐contaminant association. Bioremediation may involve aerobic or anaerobic microbial activities. Aerobic degradation often involves introduction of oxygen atoms in reactions mediated by monooxygenases, dioxygenases, hydroxylases, oxidative dehalogenases, or chemically reactive oxygen atoms generated by enzymes such as ligninases or peroxidases. Anaerobic degradations of predominant contaminants such as petroleum hydrocarbons, typically involve initial activation reactions followed by oxidative catabolism mediated by anoxic electron acceptors. Many microbes participate in bioremediation processes by mineralizing the organic contaminants to end‐products such as carbon dioxide and water, or to metabolic intermediates which are used as primary substrates for cell growth. Cells may be able to biotransform the contaminant without being able to utilize the contaminant for growth in a process known as cometabolism. Microbes have also evolved biocatalytic systems which indirectly mediate the transformation of some recalcitrant molecular species, mediated by enzymes which generate chemically reactive species which in turn, attack the recalcitrant molecules. Major strategies for implementing bioremediation processes include biostimulation and bioaugmentation approaches. Biostimulation involves adding supplements to a contaminated site with the objective of stimulating growth of the microbial population already present there, which may be capable of degrading the contaminants. Where the contaminated environment does not contain microbes capable of degrading the contaminants, there may be a case for addition of a selected and acclimated microbial inoculum. This is termed bioaugmentation. Widely used process configurations include slurry bioreactors, landfarming, soil‐pile composting systems, engineered soil piles, in situ subsurface bioremediation and phytoremediation. Bioremediation accounts only for a small fraction of the remediation market because arguably, some of the processes implemented failed to meet the required contaminant reduction criteria. For bioremediation processes to gain access to a more substantial proportion of the remediation market, processes must be judiciously selected to be technically dependable and cost‐effective.

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Regiospecific Internal Desaturation of Aliphatic Compounds by a Mutant Rhodococcus Strain

Cited by 19 publications

References 14 publications

Selective Terminal Functionalization of Linear Alkanes

Selective Terminal Functionalization of Linear Alkanes

Selective Terminal Functionalization of Linear Alkanes**

Bioremediation

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