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Terpenoids and their biosynthesis in cyanobacteria.

Pattanaik B, Lindberg P - Life (Basel) (2015)

Bottom Line: The products of the MEP pathway are the isomeric five-carbon compounds isopentenyl diphosphate and dimethylallyl diphosphate, which in turn form the basic building blocks for formation of all terpenoids.The MEP pathway, its function and regulation, and the subsequent formation of terpenoids have not been fully elucidated in cyanobacteria, despite its relevance for biotechnological applications.In this review, we summarize the present knowledge about cyanobacterial terpenoid biosynthesis, both regarding the native metabolism and regarding metabolic engineering of cyanobacteria for heterologous production of non-native terpenoids.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry-Ångström, Uppsala University, Box 523, SE-751 20 Uppsala, Sweden. bagmi.pattanaik@kemi.uu.se.

ABSTRACT
Terpenoids, or isoprenoids, are a family of compounds with great structural diversity which are essential for all living organisms. In cyanobacteria, they are synthesized from the methylerythritol-phosphate (MEP) pathway, using glyceraldehyde 3-phosphate and pyruvate produced by photosynthesis as substrates. The products of the MEP pathway are the isomeric five-carbon compounds isopentenyl diphosphate and dimethylallyl diphosphate, which in turn form the basic building blocks for formation of all terpenoids. Many terpenoid compounds have useful properties and are of interest in the fields of pharmaceuticals and nutrition, and even potentially as future biofuels. The MEP pathway, its function and regulation, and the subsequent formation of terpenoids have not been fully elucidated in cyanobacteria, despite its relevance for biotechnological applications. In this review, we summarize the present knowledge about cyanobacterial terpenoid biosynthesis, both regarding the native metabolism and regarding metabolic engineering of cyanobacteria for heterologous production of non-native terpenoids.

No MeSH data available.


Proposed terpenoid biosynthesis via the methylerythritol-4-phosphate (MEP) pathway in cyanobacteria. Abbreviations: Pyr: Pyruvate; GAP: glyceraldehyde 3-phosphate; DXP: 1-deoxy-d-xylulose 5-phosphate; MEP: methylerythritol-4-phosphate; CDP-ME: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; CDP-MEP: 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; MEcDP: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate; HMBDP: 4-hydroxy-3-methylbut-2-enyldiphosphate synthase; IDP: isopentenyl diphosphate; DMADP: dimethylallyl diphosphate; GDP: geranyl diphosphate; FDP: farnesyl diphosphate; GGDP: geranylgeranyl diphosphate; DXS: 1-deoxy-d-xylulose 5-phosphate synthase; DXR: 1-deoxy-d-xylulose 5-phosphate reductoisomerase; MCT: 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase; CMK: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol kinase; MDS: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase; HDS: 4-hydroxy-3-methylbut-2-enyl diphosphate synthase; HDR: 4-hydroxy-3-methylbut-2-enyldiphosphate reductase; IDI: isopentenyl diphosphate isomerase; GDPS: geranyl diphosphate synthase; FDPS: farnesyl diphosphate synthase; GGDPS: geranylgeranyl diphosphate synthase; TPS: terpene synthase; CP450: cytochrome P450 monooxygenase.
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life-05-00269-f001: Proposed terpenoid biosynthesis via the methylerythritol-4-phosphate (MEP) pathway in cyanobacteria. Abbreviations: Pyr: Pyruvate; GAP: glyceraldehyde 3-phosphate; DXP: 1-deoxy-d-xylulose 5-phosphate; MEP: methylerythritol-4-phosphate; CDP-ME: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; CDP-MEP: 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; MEcDP: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate; HMBDP: 4-hydroxy-3-methylbut-2-enyldiphosphate synthase; IDP: isopentenyl diphosphate; DMADP: dimethylallyl diphosphate; GDP: geranyl diphosphate; FDP: farnesyl diphosphate; GGDP: geranylgeranyl diphosphate; DXS: 1-deoxy-d-xylulose 5-phosphate synthase; DXR: 1-deoxy-d-xylulose 5-phosphate reductoisomerase; MCT: 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase; CMK: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol kinase; MDS: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase; HDS: 4-hydroxy-3-methylbut-2-enyl diphosphate synthase; HDR: 4-hydroxy-3-methylbut-2-enyldiphosphate reductase; IDI: isopentenyl diphosphate isomerase; GDPS: geranyl diphosphate synthase; FDPS: farnesyl diphosphate synthase; GGDPS: geranylgeranyl diphosphate synthase; TPS: terpene synthase; CP450: cytochrome P450 monooxygenase.

Mentions: The MEP pathway, as described for Escherichia coli [12], starts with condensation of glyceraldehyde 3-phosphate (GAP) and pyruvate to form 1-deoxy-d-xylulose 5-phosphate (DXP). Formation of DXP is an irreversible reaction catalyzed by the enzyme 1-deoxy-d-xylulose 5-phosphate synthase (DXS) with release of one molecule of CO2 (Figure 1). Involvement of DXS in the pathway was functionally analyzed for the first time in E. coli [15] and was also investigated in the cyanobacterium Synechococcus leopoliensis SAUG 1402-1 [16]. In plants, DXS plays a major role in the overall regulation of the pathway [17].


Terpenoids and their biosynthesis in cyanobacteria.

Pattanaik B, Lindberg P - Life (Basel) (2015)

Proposed terpenoid biosynthesis via the methylerythritol-4-phosphate (MEP) pathway in cyanobacteria. Abbreviations: Pyr: Pyruvate; GAP: glyceraldehyde 3-phosphate; DXP: 1-deoxy-d-xylulose 5-phosphate; MEP: methylerythritol-4-phosphate; CDP-ME: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; CDP-MEP: 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; MEcDP: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate; HMBDP: 4-hydroxy-3-methylbut-2-enyldiphosphate synthase; IDP: isopentenyl diphosphate; DMADP: dimethylallyl diphosphate; GDP: geranyl diphosphate; FDP: farnesyl diphosphate; GGDP: geranylgeranyl diphosphate; DXS: 1-deoxy-d-xylulose 5-phosphate synthase; DXR: 1-deoxy-d-xylulose 5-phosphate reductoisomerase; MCT: 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase; CMK: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol kinase; MDS: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase; HDS: 4-hydroxy-3-methylbut-2-enyl diphosphate synthase; HDR: 4-hydroxy-3-methylbut-2-enyldiphosphate reductase; IDI: isopentenyl diphosphate isomerase; GDPS: geranyl diphosphate synthase; FDPS: farnesyl diphosphate synthase; GGDPS: geranylgeranyl diphosphate synthase; TPS: terpene synthase; CP450: cytochrome P450 monooxygenase.
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Related In: Results  -  Collection

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Show All Figures
getmorefigures.php?uid=PMC4390852&req=5

life-05-00269-f001: Proposed terpenoid biosynthesis via the methylerythritol-4-phosphate (MEP) pathway in cyanobacteria. Abbreviations: Pyr: Pyruvate; GAP: glyceraldehyde 3-phosphate; DXP: 1-deoxy-d-xylulose 5-phosphate; MEP: methylerythritol-4-phosphate; CDP-ME: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; CDP-MEP: 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol; MEcDP: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate; HMBDP: 4-hydroxy-3-methylbut-2-enyldiphosphate synthase; IDP: isopentenyl diphosphate; DMADP: dimethylallyl diphosphate; GDP: geranyl diphosphate; FDP: farnesyl diphosphate; GGDP: geranylgeranyl diphosphate; DXS: 1-deoxy-d-xylulose 5-phosphate synthase; DXR: 1-deoxy-d-xylulose 5-phosphate reductoisomerase; MCT: 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase; CMK: 4-(cytidine 5'-diphospho)-2-C-methyl-d-erythritol kinase; MDS: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase; HDS: 4-hydroxy-3-methylbut-2-enyl diphosphate synthase; HDR: 4-hydroxy-3-methylbut-2-enyldiphosphate reductase; IDI: isopentenyl diphosphate isomerase; GDPS: geranyl diphosphate synthase; FDPS: farnesyl diphosphate synthase; GGDPS: geranylgeranyl diphosphate synthase; TPS: terpene synthase; CP450: cytochrome P450 monooxygenase.
Mentions: The MEP pathway, as described for Escherichia coli [12], starts with condensation of glyceraldehyde 3-phosphate (GAP) and pyruvate to form 1-deoxy-d-xylulose 5-phosphate (DXP). Formation of DXP is an irreversible reaction catalyzed by the enzyme 1-deoxy-d-xylulose 5-phosphate synthase (DXS) with release of one molecule of CO2 (Figure 1). Involvement of DXS in the pathway was functionally analyzed for the first time in E. coli [15] and was also investigated in the cyanobacterium Synechococcus leopoliensis SAUG 1402-1 [16]. In plants, DXS plays a major role in the overall regulation of the pathway [17].

Bottom Line: The products of the MEP pathway are the isomeric five-carbon compounds isopentenyl diphosphate and dimethylallyl diphosphate, which in turn form the basic building blocks for formation of all terpenoids.The MEP pathway, its function and regulation, and the subsequent formation of terpenoids have not been fully elucidated in cyanobacteria, despite its relevance for biotechnological applications.In this review, we summarize the present knowledge about cyanobacterial terpenoid biosynthesis, both regarding the native metabolism and regarding metabolic engineering of cyanobacteria for heterologous production of non-native terpenoids.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry-Ångström, Uppsala University, Box 523, SE-751 20 Uppsala, Sweden. bagmi.pattanaik@kemi.uu.se.

ABSTRACT
Terpenoids, or isoprenoids, are a family of compounds with great structural diversity which are essential for all living organisms. In cyanobacteria, they are synthesized from the methylerythritol-phosphate (MEP) pathway, using glyceraldehyde 3-phosphate and pyruvate produced by photosynthesis as substrates. The products of the MEP pathway are the isomeric five-carbon compounds isopentenyl diphosphate and dimethylallyl diphosphate, which in turn form the basic building blocks for formation of all terpenoids. Many terpenoid compounds have useful properties and are of interest in the fields of pharmaceuticals and nutrition, and even potentially as future biofuels. The MEP pathway, its function and regulation, and the subsequent formation of terpenoids have not been fully elucidated in cyanobacteria, despite its relevance for biotechnological applications. In this review, we summarize the present knowledge about cyanobacterial terpenoid biosynthesis, both regarding the native metabolism and regarding metabolic engineering of cyanobacteria for heterologous production of non-native terpenoids.

No MeSH data available.