In Ginkgo, the enzyme catalyses the initial cyclization step in the biosynthesis of ginkgolides, a structurally unique family of diterpenoids that are highly specific platelet-activating-factor receptor antagonists . Levopimaradiene is widely distributed in higher plants. In some species the enzyme also forms abietadiene, palustradiene, and neoabietadiene .
In Ginkgo, the enzyme catalyses the initial cyclization step in the biosynthesis of ginkgolides, a structurally unique family of diterpenoids that are highly specific platelet-activating-factor receptor antagonists [1]. Levopimaradiene is widely distributed in higher plants. In some species the enzyme also forms abietadiene, palustradiene, and neoabietadiene [2].
the initial products formed and released in vitro are unstable alcohols identified as epimeric thermally unstable allylic tertiary alcohols, 13-hydroxy-8(14)-abietene. The dehydration of the alcohol products, yielding the well established diterpene products levopimaradiene, abietadiene, neoabietadiene, and palustradiene, occurs due to the conditions of the GC-MS analysis typically used
abietadiene synthase (PaLAS) is a bifunctional terpene synthase that catalyzes both class I and class II reactions, i.e. formation of (+)-copalyl diphosphate from geranylgeranyl diphosphate (cf. EC 5.5.1.12, class II diTPS), and formation of abieta-8(14),12-diene from (+)-copalyl diphosphate (EC 4.2.3.32, class I diTPS)
abietadiene synthase (PaLAS) is a bifunctional terpene synthase that catalyzes both class I and class II reactions, i.e. formation of (+)-copalyl diphosphate from geranylgeranyl diphosphate (cf. EC 5.5.1.12, class II diTPS), and formation of abieta-8(14),12-diene from (+)-copalyl diphosphate (EC 4.2.3.32, class I diTPS)
resin duct epithelial cells are the main site of diterpene biosynthesis in Sitka spruce, diterpenoid biosynthesis is induced in cortical resin duct epithelial cells early upon treatment with methyljasmonate, and immature developing traumatic resin duct epithelial cells produce levopimaradiene/abietadiene synthase
levopimaradiene synthase promoter-driven expression of beta-glucuronidase in Arabidopsis shows beta-glucuronidase accumulation mainly in the epidermis of leaves, phloem of the shoots, ovaries and stamens of flowers, and vasculature of roots. Treatment of methyl jasmonate on the transformant leads to significant upregulation of the reporter gene in the roots with little change in leaves and flowers. Findings support biosynthesis of ginkgolide in the roots of Ginkgo plant and suggest translocation occurs through the phloem
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
homology model of the second active site of enzyme based on the structure of 5-epiaristolochene synthase from Nicotiana tabacum, Protein Data Bank ID code 5EAT
removal of 60 or 79 N-terminal residues increases levopimaradiene production, deletion of 128 N-terminal residues results in loss of catalytic activity
removal of 60 or 79 N-terminal residues increases levopimaradiene production, deletion of 128 N-terminal residues results in loss of catalytic activity
swapping of residues 568-640 of isopimaradiene synhase to corresponding residues 560-632 of levopimaradiene/abietadiene synthase results in complete reversion of the product profiles of the two enzymes
swapping of residues 568-640 of isopimaradiene synhase to corresponding residues 560-632 of levopimaradiene/abietadiene synthase results in complete reversion of the product profiles of the two enzymes
using a combination of protein and genetic engineering, significant improvements in the production of sclareol and several other isoprenoids is achieved, including cis-abienol, abietadiene, and beta-carotene. Recombinant expression of enzyme PaLAS in Saccharomyces cerevisiae AM94 cells, coexpression with different Saccharomyces cerevisiae farnesyl diphosphate synthase ERG20 variants increases diterpene yields by up to 15fold compared to expression of the Cistus creticus GGPPS
gene TPS-LAS, recombinant expression in Saccharomyces cerevisiae strain AM94, a yeast strain engineered for the production of isoprenoids, which contains three chromosomally integrated copies of a degradation stabilized variant of HMG2 and a heterozygous deletion of ERG9, and in strain AM204, each with or without coexpression of yeast protein Erg20p(F96C), a yeast farnesyl diphosphate synthase, overview. Coexpression with different Saccharomyces cerevisiae ERG20 variants increases diterpene yields by up to 15fold compared to expression of the Cistus creticus GGPPS
increase of levopimaradiene synthesis in Escherichia coli by amplification of the flux toward isopentenyl diphosphate and dimethylallyl diphosphate precursors and reprogramming the rate-limiting downstream pathway by generating combinatorial mutations in geranylgeranyl diphosphate synthase and levopimaradiene synthase. The most productive pathway, combining precursor flux amplification and mutant synthases, confers approximately 2600fold increase in levopimaradiene levels. A maximum titer of approximately 700 mg/l is obtained by cultivation in a benchscale bioreactor
the development of yeast strains carrying the engineered Erg20p, which support efficient isoprenoid production, e.g. by abietadiene synthase, and can be used as a dedicated chassis for diterpene production or biosynthetic pathway elucidation. The design developed can be applied to the production of any GGPP-derived isoprenoid and is compatible with other yeast terpene production platforms, method overview
Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): Functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1)
Zulak, K.G.; Dullat, H.K.; Keeling, C.I.; Lippert, D.; Bohlmann, J.
Immunofluorescence localization of levopimaradiene/abietadiene synthase in methyl jasmonate treated stems of Sitka spruce (Picea sitchensis) shows activation of diterpenoid biosynthesis in cortical and developing traumatic resin ducts