Isoprenoids in three-dimensional space: the stereochemistry of terpene biosynthesis

Dickschat, Jeroen S.

doi:10.1039/c1np00063b

Cited by 110 publications

(76 citation statements)

References 169 publications

(211 reference statements)

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“…[1][2][3] For example, from a single 15-carbon substrate, farnesyl diphosphate (FPP), terpene synthases can generate over 300 distinct products. In many cases, a terpene synthase can guide the reaction of the substrate to just one of these hundreds of possible products with high product selectivity and form multiple chiral centers in the process.…”

Section: Introductionmentioning

confidence: 99%

Improved selectivity of an engineered multi-product terpene synthase

et al. 2014

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Mutation of the sesquiterpene synthase Cop2 was conducted with a high-throughput screen for the cyclization activity using a non-natural substrate. A mutant of Cop2 was identified that contained three amino acid substitutions. This mutant, 17H2, converted the natural substrate FPP into germacrene D-4-ol with 77% selectivity. This selectivity is in contrast to that of the parent enzyme in which germacrene D-4-ol is produced as 29% and α-cadinol is produced as 46% of the product mixture. The mutations were shown to each contribute to this selectivity, and a homology model suggested that the mutations lie near to the active site though would be unlikely to be targeted for mutation by rational methods. Kinetic comparisons show that 17H2 maintains a k cat /K M of 0.62 mM −1 s −1 , which is nearly identical to that of the parent Cop2, which had a k cat /K M of 0.58 mM −1 s −1 .

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Section: Introductionmentioning

confidence: 99%

Improved selectivity of an engineered multi-product terpene synthase

et al. 2014

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“…These cascades terminate by simple deprotonation to give sesquiterpene hydrocarbons, or by attack of water to give the corresponding sesquiterpenoid alcohols. [14] We have recently investigated the volatiles of F. fujikuroi IMI58289 by use of a closed-loop stripping apparatus (CLSA) in combination with GC-MS. [11] A representative chromatogram of headspace extract is shown in Figure 1 A. Besides 2, several structurally related diterpenes were identified as side-products of the CPS/KS, by knockout experiments.…”

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Genetic Dissection of Sesquiterpene Biosynthesis by Fusarium fujikuroi

et al. 2013

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“…Their biosynthetic pathways are now being extensively studied, [1][2][3] and the base sequences of plant genomes have also recently been attracting attention. 4) A large number of terpenoid skeletons that include rearrangements and bond fission reactions have been reported.…”

Section: Introductionmentioning

confidence: 99%

Terpenoid Composition and Base Sequences of <i>Ligularia virgaurea</i> (Asteraceae) Grown in the Hengduan Mountain Area in China and a Comment on Drawing Structures

Tori

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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A chemical analysis of 30 samples of Ligularia virgaurea (Asteraceae) collected in Sichuan province and its adjacent territories in China was reviewed. These samples afforded 146 compounds, 73 of which were novel, and the chemical constituents were classified into 8 categories: (1) simple eremophilanes (without ring C) and eudesmanes including nor-derivatives, (2) furanoeremophilanes and lactones with a 1(10)-saturated bond, (3) furanoeremophilanes and lactones with a 1(10)-unsaturated bond, 1,10-epoxide, or 10-ol, (4) furanoeremophilanes and lactones with 1(10)-en-2-one, 1(10)-en-2-ol, or 1-en-3-one, (5) furanoeremophilanes and lactones with 1(10)-en-9-one, 1(10)-en-9-ol, or 1,10-epoxy-9-one, (6) cacalol and their derivatives, (7) bakkanes and their derivatives, and (8) others, as shown in Tables 1-7. In these studies, five chemotypes were identified in addition to three clades from the DNA sequences of L. virgaurea. The structural determination of some compounds was also discussed and a comment on how to express the real structure was proposed, particularly for spiro compounds.

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Isoprenoids in three-dimensional space: the stereochemistry of terpene biosynthesis

Cited by 110 publications

References 169 publications

Improved selectivity of an engineered multi-product terpene synthase

Improved selectivity of an engineered multi-product terpene synthase

Genetic Dissection of Sesquiterpene Biosynthesis by Fusarium fujikuroi

Terpenoid Composition and Base Sequences of <i>Ligularia virgaurea</i> (Asteraceae) Grown in the Hengduan Mountain Area in China and a Comment on Drawing Structures

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