5.4.99.41: lupeol synthase
This is an abbreviated version!
For detailed information about lupeol synthase, go to the full flat file.
Word Map on EC 5.4.99.41
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5.4.99.41
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triterpene
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triterpenoids
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cycloartenol
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cyclases
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beta-amyrin
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pentacyclic
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betulinic
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oleanolic
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epoxidase
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mangrove
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glycyrrhizin
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lanosterol
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taraxacum
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phytosterols
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dandelion
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oleanane
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kandelia
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glabra
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oleanane-type
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soyasaponins
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taraxerol
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bglus
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rhizophoraceae
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candel
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bruguiera
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gymnorrhiza
- 5.4.99.41
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triterpene
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triterpenoids
- cycloartenol
- cyclases
- beta-amyrin
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pentacyclic
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betulinic
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oleanolic
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epoxidase
- mangrove
- glycyrrhizin
- lanosterol
- taraxacum
- phytosterols
- dandelion
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oleanane
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kandelia
- glabra
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oleanane-type
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soyasaponins
- taraxerol
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bglus
- rhizophoraceae
- candel
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bruguiera
- gymnorrhiza
Reaction
Synonyms
2,3-oxidosqualene-triterpenoid cyclase, At1g78970, AtLUP1, BPY, LUP1, lupeol synthase, LUS, MdOSC5, OEW, OSC3, OSC5, RcLUS, TRW
ECTree
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Engineering
Engineering on EC 5.4.99.41 - lupeol synthase
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L256A
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mutation in region responsible for product differentiation. Mutant produces 3.8% beta-amyrin, 69.5% lupeol, 10% butyrospermol and 13.5% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
L256F
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mutation in region responsible for product differentiation. Mutant produces 9.8% beta-amyrin, 69.7% lupeol, 17.9% butyrospermol
L256H
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mutation in region responsible for product differentiation. Mutant produces 3.8% beta-amyrin, 69.5% lupeol, 10% butyrospermol and 13.5% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
L256W
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mutation in region responsible for product differentiation. Mutant produces 74.8% beta-amyrin, 6.9% lupeol, 9.9% butyrospermol and 8.4% germanicol
L256Y
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mutation in region responsible for product differentiation. Mutant produces 1.6% beta-amyrin, 54.8% lupeol, 22.7% butyrospermol and 18.7% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
Y258H
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mutation in region responsible for product differentiation. Mutant produces 43.6% lupeol, 6.2% butyrospermol and 42.4% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
yes
functional expression in Sacchaormyces cerevisiae results in production of lupeol
additional information
construction of chimera between Arabidopsis thaliana YUP8H12R.43 multifunctional triterpene synthase and LUP1 lupeol synthase. Mutant with N-terminal half of LUP1 and C-terminal half of YUP8H12R.43 gives a product pattern similar to native LUP1 with increased production of minor compounds. Mutant LUP1 containing amino acids corresponding to residues 184 to 398 from YUP8H12R.43 gives an almost identical product pattern with native LUP1. Mutant YUP8H12R.43 containing amino acids corresponding to residues 184 to 395 from LUP1 shows similar product multiplicity to that observed in YUP8H12R.43
additional information
construction of chimeric proteins using beta-amyrin synthase from Panax ginseng and lupeol synthase from Arabidopsis thaliana. Chimera with N-terminal half of beta-amyrin synthase and C-terminal half of lupeol synthase produces beta-amyrin and lupeol in ratio 3:1. Chimera with only the second quarter of the N-terminus from beta-amyrin synthase, produces beta-amyrin and lupeol in a 4:1 ratio, while another chimera created by mixed PCR produces beta-amyrin and lupeol in a 1:4 ratio
additional information
functional expression in Saccharomyces cerevisiae lacking lanosterol synthase activity results in production of lupeol
additional information
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functional expression in Saccharomyces cerevisiae lacking lanosterol synthase activity results in production of lupeol
additional information
2,3-oxidosqualene production is implemented and subsequently combined with different cyclization reactions catalyzed by the representative oxidosqualene cyclases CAS1 (cycloartenol synthase), LUP1 (lupeol synthase), THAS1 (thalianol synthase) and MRN1 (marneral synthase), derived from model plant Arabidopsis thaliana, in the two alternative hosts for biosynthesis of cyclic plant triterpenes, the metabolically versatile photosynthetic alpha-proteobacterium Rhodobacter capsulatus strain SB1003 and cyanobacterium Synechocystis sp. PCC 6803, triterpene pathway design, overview. While successful accumulation of 2,3-oxidosqualene can be detected by LC-MS analysis in both hosts, cyclase expression results in differential production profiles. CAS1 catalyzes conversion to only cycloartenol, but expression of LUP1 yields lupeol and a triterpenoid matching an oxidation product of lupeol, lupX, in both hosts. In contrast, THAS1 expression does not lead to cyclic product formation in either host, whereas MRN1-dependent production of marnerol and hydroxymarnerol is observed in Synechocystis but not in Rhodobacter capsulatus. 2,3-Oxidosqualene cyclization in heterologous phototrophic bacteria is basically feasible but efficient conversion depends on both the respective cyclase enzyme and individual host properties
additional information
functional expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase activity results in production of lupeol
additional information
functional expression in Saccharomyces cerevisiae results in production of lupeol
additional information
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functional expression in Saccharomyces cerevisiae results in production of lupeol
additional information
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functional expression in Saccharomyces cerevisiae mutant with disruption in oxidosqualene cyclase gene results in production of lupeol
additional information
transient expression of MdOSC1 and MdOSC5 together with CYP716A175 confirms the ratio between the different triterpene backbones observed after transient expression of MdOSC1 and MDOSC5 alone, overview
additional information
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transient expression of MdOSC1 and MdOSC5 together with CYP716A175 confirms the ratio between the different triterpene backbones observed after transient expression of MdOSC1 and MDOSC5 alone, overview
additional information
expression in Saccharomyces cerevisiae lacking in lanosterol synthase activity results in production of lupeol
additional information
expression in Saccharomyces cerevisiae lacking in lanosterol synthase activity results in production of lupeol
additional information
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expression in Saccharomyces cerevisiae lacking in lanosterol synthase activity results in production of lupeol