Genes and Pathways Involved in Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids in Bacteria

Ootaki, Michiru; Morita, Naoki; Nishida, Takanori; Tanaka, Mika; Hase, Akira; Yano, Yutaka; Yamada, Akiko; Yu, Reiko; Watanabe, Kazuo; Okuyama, Hidetoshi

doi:10.1007/978-94-017-0159-4_10

Cited by 4 publications

(7 citation statements)

References 4 publications

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“…Similar systems could be constructed for DHA by isolating individual pfa genes involved in DHA production. A biosynthetic mechanism has been proposed for EPA (and probably DHA) production, which is similar to the anaerobic pathway of unsaturated fatty acid biosynthesis (7,16). However, no direct evidence is available to support this proposed mechanism.…”

Section: Future Perspectivesmentioning

confidence: 99%

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Bacterial Genes Responsible for the Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids and Their Heterologous Expression

Okuyama

Orikasa

Nishida

et al. 2007

Appl Environ Microbiol

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120

118

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Section: Future Perspectivesmentioning

confidence: 99%

“…There are some variations in the structures of pfa gene clusters, although they have a basic structure that is common among all types of clusters (see below). There is no doubt that all bacterial EPA and DHA are synthesized by the PKS system (7,16).…”

mentioning

confidence: 99%

Bacterial Genes Responsible for the Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids and Their Heterologous Expression

Okuyama

Orikasa

Nishida

et al. 2007

Appl Environ Microbiol

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120

118

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“…The same compound (C31:9) was detected in marine and nonmarine, and psychrophilc and mesophilic bacteria, which contained EPA and/or DHA (Table 4). Based on our present results, previous studies on the bacterial distribution of PUFAs and pfa genes [3], and data on the predicted biosynthetic pathway of PUFAs in the polyketide synthesis mode [37,39,40], we will discuss the biosynthetic routes of C31:9.…”

Section: Discussionmentioning

confidence: 60%

Possible Biosynthetic Pathways for all cis‐3,6,9,12,15,19,22,25,28‐Hentriacontanonaene in Bacteria

Sugihara

Hori

Nakanowatari

et al. 2009

Lipids

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A very long chain polyunsaturated hydrocarbon, hentriacontanonaene (C31:9), was detected in an eicosapentaenoic acid (EPA)-producing marine bacterium, which was isolated from the mid-latitude seashore of Hokkaido, Japan, and was tentatively identified as mesophilic Shewanella sp. strain osh08 from 16S rRNA gene sequencing. The geometry and position of the double bonds in this compound were determined physicochemically to be all cis at positions 3, 6, 9, 12, 15, 19, 22, 25, and 28. Although C31:9 was detected in all of the seven EPA-or/and docosahexaenoic acid-producing bacteria tested, an EPA-deficient mutant (strain IK-18) of one of these bacteria had no C31:9. Strain IK-18 had defects in the pfaD gene, one of the five pfa genes responsible for the biosynthesis of EPA.Although Escherichia coli DH5 does not produce EPA or DHA inherently, cells transformed with the pfa genes responsible for the biosynthesis of EPA and DHA produced EPA and DHA, respectively, but not C31:9. These results suggest that the Pfa protein complex is involved in the biosynthesis of C31:9 and that pfa genes must not be the only genes responsible for the formation of C31:9. In this report, we determined for the first time the molecular structure of the C31:9 and discuss the possible biosynthetic pathways of this compound. Key words

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“…Intermediates before 4,7,10,13–16:4 were omitted. This pathway is slightly modified from that presented previously (Ootaki et al , 2003).…”

Section: Resultsmentioning

confidence: 99%

“…The process requires three steps: condensation of the elongating fatty acid and the C2 donor (malonyl-ACP), introduction of a double bond by dehydration and the subsequent geometric or positional isomerization of the double bond, although no direct experimental evidence of this has ever been reported. Ootaki et al (2003) speculated that 3,6,9,12,15-octadecapentaenoic acid (18:5) is one of the intermediate fatty acids, at which point the pathway branches into EPA or DHA biosynthesis (Fig. 2).…”

Section: Resultsmentioning

confidence: 99%

pfaBproducts determine the molecular species produced in bacterial polyunsaturated fatty acid biosynthesis

Orikasa

Tanaka

Sugihara

et al. 2009

FEMS Microbiology Letters

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When pDHA4, a vector carrying all five pfaA-pfaE genes responsible for docosahexaenoic acid (DHA; 22:6) biosynthesis in Moritella marina MP-1, was coexpressed in Escherichia coli with the individual pfaA-pfaD genes for eicosapentaenoic acid (EPA; 20:5) biosynthesis from Shewanella pneumatophori SCRC-2738, both polyunsaturated fatty acids were synthesized only in the recombinant carrying pfaB for EPA synthesis. Escherichia coli coexpressing a deleted construct comprising pfaA, pfaC, pfaD and pfaE for EPA and pfaB for DHA produced EPA and DHA. Both EPA and DHA were detected in bacteria that inherently contained pfa genes for DHA. These results suggest that PfaB is the key enzyme determining the final product in EPA or DHA biosynthesis.

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Genes and Pathways Involved in Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids in Bacteria

Cited by 4 publications

References 4 publications

Bacterial Genes Responsible for the Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids and Their Heterologous Expression

Bacterial Genes Responsible for the Biosynthesis of Eicosapentaenoic and Docosahexaenoic Acids and Their Heterologous Expression

Possible Biosynthetic Pathways for all cis‐3,6,9,12,15,19,22,25,28‐Hentriacontanonaene in Bacteria

pfaBproducts determine the molecular species produced in bacterial polyunsaturated fatty acid biosynthesis

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