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Information on EC 2.4.1.85 - cyanohydrin beta-glucosyltransferase
for references in articles please use BRENDA:EC2.4.1.85
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EC Tree 2 Transferases
2.4 Glycosyltransferases
2.4.1 Hexosyltransferases
2.4.1.85 cyanohydrin beta-glucosyltransferase
IUBMB Comments
Acts on a wide range of substrates in vitro, including cyanohydrins, terpenoids, phenolics, hexanol derivatives and plant hormones, in a regiospecific manner . This enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum, along with EC 1.14.14.36, tyrosine N-monooxygenase and EC 1.14.14.37, 4-hydroxyphenylacetaldehyde oxime monooxygenase. This reaction prevents the disocciation and release of toxic hydrogen cyanide .
The enzyme appears in viruses and cellular organisms
- 2.4.1.85
- sorghum
-
cyanogenic
- dhurrin
- bicolor
-
glucosylates
- cyp71e1
-
three-fold
-
bitterness
-
stereo-selectively
-
r-mandelonitrile
-
quantitative-pcr
- diglucoside
- testa
-
mill
- amygdalus
- kernels
- batsch
-
prunus
- prunasin
-
metabolons
-
compartmentalised
-
non-bitter
- dulcis
- rosaceae
- almond
-
erratum
-
hypervariable
-
regiospecificity
- geraniol
- udp-glucosyltransferase
- agriculture
- biotechnology
- synthesis
Reaction Schemes
showSynonyms
ugt85b1, udp-glucose:p-hydroxymandelonitrile-o-glucosyltransferase, mandelonitrile glucosyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
glucosyltransferase, uridine diphosphoglucose-p-hydroxymandelonitrile
-
-
-
-
UDP-glucose-p-hydroxymandelonitrile glucosyltransferase
-
-
-
-
UGT85B1
uridine diphosphoglucose-cyanohydrin glucosyltransferase
-
-
-
-
uridine diphosphoglucose-p-hydroxymandelonitrile glucosyltransferase
-
-
-
-
uridine diphosphoglucose:aldehyde cyanohydrin beta-glucosyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + (S)-4-hydroxymandelonitrile = UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
dhurrin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
UDP-D-glucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase
Acts on a wide range of substrates in vitro, including cyanohydrins, terpenoids, phenolics, hexanol derivatives and plant hormones, in a regiospecific manner [3]. This enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum, along with EC 1.14.14.36, tyrosine N-monooxygenase and EC 1.14.14.37, 4-hydroxyphenylacetaldehyde oxime monooxygenase. This reaction prevents the disocciation and release of toxic hydrogen cyanide [3].
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CAS REGISTRY NUMBER
COMMENTARY
55354-52-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-alpha-D-glucose + phenol
UDP + phenyl beta-D-glucopyranoside
-
Substrates: very poor substrate
Products: -
Products: -
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDP-glucose + (R,S)-mandelonitrile
UDP + prunasin
Substrates: -
Products: -
Products: -
ir
UDP-glucose + 1-hexanol
UDP + hexyl beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 2-hydroxy-2-methylbutyronitrile
UDP + ?
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 2-hydroxy-3-methoxybenzyl alcohol
UDP + ?
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 3-methyl-2-buten-1-ol
UDP + 3-methyl-2-butenyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 3-methyl-3-buten-1-ol
UDP + 3-methyl-3-butenyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-formylphenyl beta-D-glucopyranoside
-
Substrates: poor substrate, mixture of 4-hydroxybenzaldehyde with NaCN: good substrate
Products: -
Products: -
?
UDP-glucose + 4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + alpha-terpinol
UDP + alpha-terpinyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + benzyl alcohol
UDP + benzyl beta-D-glucoside
Substrates: -
Products: -
Products: -
?
UDP-glucose + beta-citronellol
UDP + beta-citronellol beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + cis-3-hexen-1-ol
UDP + cis-3-hexenyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + farnesol
UDP + farnesyl beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + geraniol
UDP + geranyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + linalool
UDP + linalool beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + mandelonitrile
UDP + 2-(beta-D-glucopyranosyl)-2-phenylacetonitrile
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + mandelonitrile
UDP + mandelonitrile beta-D-glucoside
Substrates: specific for UDP-glucose
Products: -
Products: -
?
UDP-glucose + nerol
UDP + nerol beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + trans-2-hexen-1-ol
UDP + trans-2-hexenyl-beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + vanillic acid
UDP + vanillic acid beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDP-glucose + vanillin
UDP + vanillin beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDPalpha-D-glucose + benzoic acid
UDP + 1-O-benzoyl-beta-D-glucose
Substrates: at 4% of the rate with p-hydroxymandelonitrile
Products: -
Products: -
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDPglucose + 4-hydroxybenzoic acid
UDP + glucosyl-4-hydroxybenzoate
-
Substrates: poor substrate
Products: -
Products: -
?
UDPglucose + 4-hydroxybenzyl alcohol
UDP + 4-hydroxybenzyl glucoside
-
Substrates: at 36% the rate of 4-hydroxymandelonitrile
Products: -
Products: -
?
UDPglucose + benzyl alcohol
UDP + benzylglucoside
Substrates: at 13% of the rate with p-hydroxymandelonitrile
Products: -
Products: -
?
UDPglucose + geraniol
UDP + geraniol glucoside
Substrates: at 11% of the rate with p-hydroxymandelonitrile
Products: -
Products: -
?
UDPglucose + hydroquinone
UDP + hydroquinone glucoside
-
Substrates: at 41% the rate of 4-hydroxymandelonitrile
Products: -
Products: -
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: -
Products: i.e. dhurrin
Products: i.e. dhurrin
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: the glucosylation stabilizes the labile cyanohydrin
Products: i.e. dhurrin
Products: i.e. dhurrin
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: -
Products: i.e. dhurrin
Products: i.e. dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: -
Products: identical with dhurrin
Products: identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: C-terminal region encodes the UDPglucose binding domain
Products: identical with dhurrin
Products: identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: stereospecific for the S-enantiomer
Products: identical with dhurrin
Products: identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: stereospecific for the S-enantiomer
Products: identical with dhurrin
Products: identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: involved in dhurrin biosynthesis
Products: dhurrin is the cyanogenic glucoside characteristic of Sorghum species
Products: dhurrin is the cyanogenic glucoside characteristic of Sorghum species
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: endogenous substrate is p-hydroxymandelonitrile, final step in the biosynthesis of dhurrin, transformation of the labile cyanohydrin into a stable storage form
Products: -
Products: -
?
UDPglucose + (S)-mandelonitrile
UDP + (S)-mandelonitrile beta-D-glucoside
Substrates: at 78% of the rate with p-hydroxymandelonitrile
Products: -
Products: -
?
UDPglucose + (S)-mandelonitrile
UDP + (S)-mandelonitrile beta-D-glucoside
-
Substrates: as good as 4-hydroxymandelonitrile
Products: -
Products: -
?
additional information
?
-
-
Substrates: final enzyme of dhurrin biosynthesis
Products: -
Products: -
?
additional information
?
-
Substrates: UGT85B1 has a broad substrate specificity
Products: -
Products: -
?
additional information
?
-
-
Substrates: UGT85B1 has a broad substrate specificity
Products: -
Products: -
?
additional information
additional information
-
-
Substrates: reaction is specific for an aromatic group, but not for a p-hydroxy substituent on the aromatic group, no substrates: catechol, resorcinol, phloroglucinol, fructose, glucose, dhurrin, acetone cyanohydrin, acetaldehyde cyanohydrin, GDPglucose, TDPglucose, ADPglucose
Products: no product: taxiphyllin
Products: no product: taxiphyllin
?
additional information
additional information
-
Substrates: exclusively specific for the presence of a benzyl group in the substrate, no substrate: acetone cyanohydrin, hydroquinone, p-hydroxybenzaldehyde, gentisic acid, caffeic acid, 2-hydroxy cinnamic acid, resveratrol, salicylic acid, p-hydroxymandelic acid, quercetin, caynidin, biochanin A, naringenin, apigenin, indole acetic acid, tomatidine
Products: -
Products: -
?
additional information
additional information
-
-
Substrates: exclusively specific for the presence of a benzyl group in the substrate, no substrate: acetone cyanohydrin, hydroquinone, p-hydroxybenzaldehyde, gentisic acid, caffeic acid, 2-hydroxy cinnamic acid, resveratrol, salicylic acid, p-hydroxymandelic acid, quercetin, caynidin, biochanin A, naringenin, apigenin, indole acetic acid, tomatidine
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDP-glucose + (R,S)-mandelonitrile
UDP + prunasin
Substrates: -
Products: -
Products: -
ir
UDP-glucose + 4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: -
Products: -
Products: -
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
additional information
?
-
-
Substrates: final enzyme of dhurrin biosynthesis
Products: -
Products: -
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: -
Products: i.e. dhurrin
Products: i.e. dhurrin
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: the glucosylation stabilizes the labile cyanohydrin
Products: i.e. dhurrin
Products: i.e. dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
Substrates: involved in dhurrin biosynthesis
Products: dhurrin is the cyanogenic glucoside characteristic of Sorghum species
Products: dhurrin is the cyanogenic glucoside characteristic of Sorghum species
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
Substrates: endogenous substrate is p-hydroxymandelonitrile, final step in the biosynthesis of dhurrin, transformation of the labile cyanohydrin into a stable storage form
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxybenzaldehyde
potent inhibitor, 1 mg/ml bovine serum albumin protects
4-hydroxymandelonitrile
possibly an inhibitor, 1 mg/ml bovine serum albumin protects
mandelonitrile
potent inhibitor, 1 mg/ml bovine serum albumin protects
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
activity is 3fold greater in bitter almonds than in non-bitter types
brenda
additional information
-
68% of enzyme activity in epidermal and 32% in mesophyllic tissue
brenda
-
71% of enzyme activity in epidermal and 29% in mesophyllic tissue
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
UGT85B1 is found mainly in the soluble stroma fraction
brenda
transient expression of a fluorescent fusion protein in Sorghum bicolor epidermal cells as monitored by confocal laser scanning microscopy shows that UGT85B1-YFP accumulates in the cytoplasm in the absence of CYP79A1 or CYP71E1
brenda
transient expression of a fluorescent fusion protein in Sorghum bicolor epidermal cells as monitored by confocal laser scanning microscopy shows that UGT85B1-YFP in the presence of CYP79A1 and CYP71E1 shifts towards the surface of the ER membrane in the periphery of biosynthetic active cells
brenda
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
plant tcd2 mutants deficient in the enzyme have reduced vigor, being dwarfed, with poor root development and low fertility. The mutant plants accumulate numerous dhurrin pathway-derived metabolites, some of which are similar to those observed in transgenic Arabidopsis thaliana expressing the CYP79A1 and CYP71E1 genes. The tcd2 mutant suffers from self-intoxication because Sorghum does not have a feedback mechanism to inhibit the initial steps of dhurrin biosynthesis when the glucosyltransferase activity required to complete the synthesis of dhurrin is lacking. Phenotype, detailed overview
metabolism
physiological function
metabolism
glucosylation of R-mandelonitrile to prunasin which is a precursor of amygdalin
metabolism
-
UGT85B1 is an important step in product channelling because a rapid glucosylation of the labile p-hydroxymandelonitrile product of CYP71E1 is necessary to avoid its dissociation into p-hydroxybenzaldehyde and hydrogen cyanide
metabolism
dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase
metabolism
dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase. Dhurrin biosynthesis in Sorghum and the formation of products derived from the different intermediates as part of the detoxification processes or as putative turnover products identified in the tcd2 mutant, overview
physiological function
enzyme UGT85B1 is essential for formation of dhurrin in sorghum with no co-expressed endogenous UDP-glucosyltransferases able to replace it. Presence of metabolites in the tcd2 mutant which are suggested to be derived from dhurrin via endogenous pathways for nitrogen recovery, indicating which enzymes may be involved in such pathways, metabolites identification by LC-MS
physiological function
-
key gene involved in salt tolerance due to its possible role in dhurrin biosynthesis under salt stress
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E410A
glucosylation of mandelonitrile is 225fold reduced compared to wild-type enzyme
R201A
glucosylation of mandelonitrile is 20fold reduced compared to wild-type enzyme
S391A
glucosylation of mandelonitrile is 185fold reduced compared to wild-type enzyme
additional information
additional information
transgenic Arabidopsis thaliana plants that produce dhurrin are obtained by co-expression of CYP79A1/CYP71E1-CFP (cyan fluorescent protein)/UGT85B1-YFP (yellow fluorescent protein) and of CYP79A1/CYP71E1/UGT85B1-YFP (yellow fluorescent protein)
additional information
-
transgenic Arabidopsis thaliana plants that produce dhurrin are obtained by co-expression of CYP79A1/CYP71E1-CFP (cyan fluorescent protein)/UGT85B1-YFP (yellow fluorescent protein) and of CYP79A1/CYP71E1/UGT85B1-YFP (yellow fluorescent protein)
additional information
engineering for introduction of the dhurrin biosynthesis pathway, starting with L-tyrosine and comprising the enzymes CYP79A1, CYP71E1, and UGT85B1 into Nicotiana tabacum. Integration of genes CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the Nicotiana tabacum chloroplast genome and functional expression, overview. The enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor
additional information
-
engineering for introduction of the dhurrin biosynthesis pathway, starting with L-tyrosine and comprising the enzymes CYP79A1, CYP71E1, and UGT85B1 into Nicotiana tabacum. Integration of genes CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the Nicotiana tabacum chloroplast genome and functional expression, overview. The enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor
additional information
construction of a knockout mutant by use of targeted induced local lesions in genomes (TILLING) to identify a line with a mutation resulting in a premature stop codon in the N-terminal region of UGT85B1. Plants homozygous for this mutation do not produce dhurrin and are designated tcd2 (totally cyanide deficient 2) mutants. Phenotype, detailed overview
additional information
-
construction of a knockout mutant by use of targeted induced local lesions in genomes (TILLING) to identify a line with a mutation resulting in a premature stop codon in the N-terminal region of UGT85B1. Plants homozygous for this mutation do not produce dhurrin and are designated tcd2 (totally cyanide deficient 2) mutants. Phenotype, detailed overview
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
activity is largely uneffected by both freezing at -80°C and addition of glycerol, DTT stabilizes
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 2 days, lowering the concentration of DTT from 5 to 2 mM results in a 10fold decrease in activity
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
420fold, native and recombinant enzyme, expressed in Escherichia coli JM109
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning of a full-length cDNA encoding enzyme, expression in Escherichia coli JM109, 492-amino acids translation product
gene UGT85B1, DNA and amino acid sequence determination and analysis of wild-type and mutant tcd2 genes. The CYP79A1, CYP71E1 and UGT85B1 genes required for dhurrin synthesis are clustered
recombinant expression in Nicotiana tabacum chloroplasts, coexpression with CYP79A1 and CYP71E1 linked in a tricistronic operon construct with the essential regulatory elements
transgenic Arabidopsis thaliana plants expressing the entire biosynthetic pathway for the tyrosine-derived cyanogenic glucoside dhurrin as accomplished by insertion of CYP79A1, CYP71E2, and UFT85B1 are shown to accumulate 4% dry-weight dhurrin with marginal inadvertent effects on plant morphology, free amino acid pools, transcriptome, and metabolome
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
-
it is possible to engineer plants (Arabidopsis thaliana) which express the high flux pathway for dhurrin synthesis
biotechnology
integration of genes CYP79A1, CYP71E1, and UGT85B1 in Nicotiana tabacum chloroplast genome and functional expression, the enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor. Plant P450s involved in the synthesis of economically important compounds can be engineered into the thylakoid membrane of chloroplasts, and their full catalytic cycle can be driven directly by photosynthesis-derived electrons
synthesis
integration of genes CYP79A1, CYP71E1, and UGT85B1 in Nicotiana tabacum chloroplast genome and functional expression, the enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor. Plant P450s involved in the synthesis of economically important compounds can be engineered into the thylakoid membrane of chloroplasts, and their full catalytic cycle can be driven directly by photosynthesis-derived electrons
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kojima, M.; Poulton, J.E.; Thayer, S.S.; Conn, E.E.
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brenda
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Sorghum bicolor
brenda
Surkin Wurtele, E.; Thayer, S.S.; Conn, E.E.
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Sorghum bicolor
brenda
Jones, P.R.; Moller, B.L.; Hoj, P.B.
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Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
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Sorghum bicolor
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Thorsoe, K.S.; Bak, S.; Olsen, C.E.; Imberty, A.; Breton, C.; Moller, B.L.
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Sorghum bicolor (Q9SBL1), Sorghum bicolor
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Kristensen, C.; Morant, M.; Olsen, C.E.; Ekstrom, C.T.; Galbraith, D.W.; Moller, B.L.; Bak, S.
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome
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2005
Sorghum bicolor
brenda
Nielsen, K.A.; Tattersall, D.B.; Jones, P.R.; Muller, B.L.
Metabolon formation in dhurrin biosynthesis
Phytochemistry
69
88-98
2008
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Franks, T.; Yadollahi, A.; Wirthensohn, M.; Guerin, J.; Kaiser, B.; Sedgley, M.; Ford, C.
A seed coat cyanohydrin glucosyltransferase is associated with bitterness in almond (Prunus dulcis) kernels
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35
236-246
2008
Prunus dulcis (B2XBQ5)
-
brenda
Jensen, K.; Osmani, S.A.; Hamann, T.; Naur, P.; Moller, B.L.
Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions
Phytochemistry
72
2113-2123
2011
Sorghum bicolor
brenda
Gnanasekaran, T.; Karcher, D.; Nielsen, A.Z.; Martens, H.J.; Ruf, S.; Kroop, X.; Olsen, C.E.; Motawie, M.S.; Pribil, M.; M?ller, B.L.; Bock, R.; Jensen, P.E.
Transfer of the cytochrome P450-dependent dhurrin pathway from Sorghum bicolor into Nicotiana tabacum chloroplasts for light-driven synthesis
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67
2495-2506
2016
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Blomstedt, C.K.; O'Donnell, N.H.; Bjarnholt, N.; Neale, A.D.; Hamill, J.D.; Moeller, B.L.; Gleadow, R.M.
Metabolic consequences of knocking out UGT85B1, the gene encoding the glucosyltransferase required for synthesis of dhurrin in Sorghum bicolor (L. Moench)
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57
373-386
2016
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Jeon, D.; Kim, J.B.; Kang, B.C.; Kim, C.
Deciphering the genetic mechanisms of salt tolerance in Sorghum bicolor L. key genes and SNP associations from comparative transcriptomic analyses
Plants (Basel)
12
2639
2023
Sorghum bicolor
brenda
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