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The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

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Minimum Set of Cytochromes P450 for Reconstituting the Biosynthesis of Camalexin, a Major Arabidopsis Antibiotic

inferredcites →https://doi.org/10.1002/jlcr.2580140504openalex-snapshot

Chemical synthesis of labelled intermediates in cyanogenic glucoside biosynthesis

inferredcites →https://doi.org/10.1006/abbi.1995.0024openalex-snapshot

The Primary Sequence of Cytochrome P450tyr, the MultifunctionalN-Hydroxylase Catalyzing the Conversion ofL-Tyrosine top-Hydroxyphenylacetaldehyde Oxime in the Biosynthesis of the Cyanogenic Glucoside Dhurrin inSorghum bicolor(L.) Moench

inferredcites →https://doi.org/10.1006/abbi.1998.1068openalex-snapshot

Substrate Specificity of the Cytochrome P450 Enzymes CYP79A1 and CYP71E1 Involved in the Biosynthesis of the Cyanogenic Glucoside Dhurrin inSorghum bicolor(L.) Moench

inferredcites →https://doi.org/10.1007/s007260200014openalex-snapshot

Biosynthesis and metabolic engineering of glucosinolates.

inferredcites →https://doi.org/10.1007/s10886-006-9205-xopenalex-snapshot

Cyanide in the Chemical Arsenal of Garlic Mustard, Alliaria petiolata

inferredcites →https://doi.org/10.1007/s10886-014-0509-yopenalex-snapshot

Glucosinolate-Related Glucosides in Alliaria petiolata: Sources of Variation in the Plant and Different Metabolism in an Adapted Specialist Herbivore, Pieris rapae

inferredcites →https://doi.org/10.1007/s11101-006-9033-1openalex-snapshot

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

inferredcites →https://doi.org/10.1016/0003-2697(77)90700-xopenalex-snapshot

Intermediates in the biosynthesis of cyanogenic glucosides determined by use of a gas chromatograph coupled with a gas proportional counter

inferredcites →https://doi.org/10.1016/j.bbapap.2007.04.010openalex-snapshot

Purification and partial characterization of N-hydroxy-l-phenylalanine decarboxylase/oxidase from Bacillus sp. strain OxB-1, an enzyme involved in aldoxime biosynthesis in the “aldoxime–nitrile pathway”

inferredcites →https://doi.org/10.1016/j.pbi.2010.01.009openalex-snapshot

Functional diversifications of cyanogenic glucosides

inferredcites →https://doi.org/10.1016/j.phytochem.2007.06.033openalex-snapshot

Metabolon formation in dhurrin biosynthesis

inferredcites →https://doi.org/10.1016/j.phytochem.2008.01.022openalex-snapshot

Diversification of an ancient theme: Hydroxynitrile glucosides

inferredcites →https://doi.org/10.1016/j.phytochem.2008.02.019openalex-snapshot

Cyanogenesis in plants and arthropods

inferredcites →https://doi.org/10.1016/j.phytochem.2008.04.018openalex-snapshot

Hydroxynitrile glucosides

inferredcites →https://doi.org/10.1016/j.phytochem.2008.08.014openalex-snapshot

Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes

inferredcites →https://doi.org/10.1016/j.phytochem.2012.01.020openalex-snapshot

Biosynthesis of rhodiocyanosides in Lotus japonicus: Rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile

inferredcites →https://doi.org/10.1016/j.toxlet.2009.05.007openalex-snapshot

Effects of oximes on mitochondrial oxidase activity

inferredcites →https://doi.org/10.1016/j.tplants.2013.01.001openalex-snapshot

Plant chemical defense: at what cost?

inferredcites →https://doi.org/10.1016/s0021-9258(17)45334-8openalex-snapshot

The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate.

inferredcites →https://doi.org/10.1016/s0021-9258(19)47140-8openalex-snapshot

The biosynthesis of cyanogenic glucosides in higher plants

inferredcites →https://doi.org/10.1016/s0021-9258(19)85850-7openalex-snapshot

The biosynthesis of cyanogenic glucosides in higher plants. Channeling of intermediates in dhurrin biosynthesis by a microsomal system from Sorghum bicolor (linn) Moench.

inferredcites →https://doi.org/10.1016/s0021-9258(19)86931-4openalex-snapshot

The biosynthesis of cyanogenic glucosides in higher plants. N-Hydroxytyrosine as an intermediate in the biosynthesis of dhurrin by Sorghum bicolor (Linn) Moench.

inferredcites →https://doi.org/10.1016/s0031-9422(00)00316-2openalex-snapshot

The chemical diversity and distribution of glucosinolates and isothiocyanates among plants

inferredcites →https://doi.org/10.1021/bi00191a008openalex-snapshot

Dehydration of Alkyl- and Arylaldoximes as a New Cytochrome P450-Catalyzed Reaction: Mechanism and Stereochemical Characteristics

inferredcites →https://doi.org/10.1021/bi991598uopenalex-snapshot

Novel Heme-Containing Lyase, Phenylacetaldoxime Dehydratase from Bacillus sp. Strain OxB-1: Purification, Characterization, and Molecular Cloning of the Gene,

inferredcites →https://doi.org/10.1021/ja981805yopenalex-snapshot

New Catalytic Properties of Iron Porphyrins: Model Systems for Cytochrome P450-Catalyzed Dehydration of Aldoximes

inferredcites →https://doi.org/10.1021/jo00045a014openalex-snapshot

A Beckmann-type dehydration of n-butyraldoxime catalyzed by cytochrome P-450

inferredcites →https://doi.org/10.1021/jp205944eopenalex-snapshot

Aldoxime Dehydratase: Probing the Heme Environment Involved in the Synthesis of the Carbon–Nitrogen Triple Bond

inferredcites →https://doi.org/10.1023/a:1006064202774openalex-snapshot

The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates

inferredcites →https://doi.org/10.1038/nchembio.185openalex-snapshot

Glucosinolate engineering identifies a γ-glutamyl peptidase

inferredcites →https://doi.org/10.1046/j.1365-313x.1999.00642.xopenalex-snapshot

Metabolic engineering of p‐hydroxybenzylglucosinolate in Arabidopsis by expression of the cyanogenic CYP79A1 from Sorghum bicolor

inferredcites →https://doi.org/10.1046/j.1365-313x.2003.01679.xopenalex-snapshot

CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis

inferredcites →https://doi.org/10.1073/pnas.0409233102openalex-snapshot

Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome

inferredcites →https://doi.org/10.1073/pnas.88.2.487openalex-snapshot

2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

inferredcites →https://doi.org/10.1073/pnas.91.21.9740openalex-snapshot

Isolation of the heme-thiolate enzyme cytochrome P-450TYR, which catalyzes the committed step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

inferredcites →https://doi.org/10.1074/jbc.270.8.3506openalex-snapshot

Cytochrome P-450TYR Is a Multifunctional Heme-Thiolate Enzyme Catalyzing the Conversion of L-Tyrosine to p-Hydroxyphenylacetaldehyde Oxime in the Biosynthesis of the Cyanogenic Glucoside Dhurrin in Sorghum bicolor (L.) Moench

inferredcites →https://doi.org/10.1074/jbc.274.50.35483openalex-snapshot

The UDP-glucose:p-Hydroxymandelonitrile-O-Glucosyltransferase That Catalyzes the Last Step in Synthesis of the Cyanogenic Glucoside Dhurrin in Sorghum bicolor

inferredcites →https://doi.org/10.1074/jbc.275.19.14659openalex-snapshot

Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the Conversion of l-Phenylalanine to Phenylacetaldoxime in the Biosynthesis of Benzylglucosinolate

inferredcites →https://doi.org/10.1074/jbc.275.3.1966openalex-snapshot

Cytochromes P-450 from Cassava (Manihot esculentaCrantz) Catalyzing the First Steps in the Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin

inferredcites →https://doi.org/10.1074/jbc.m109.018762openalex-snapshot

X-ray Crystal Structure of Michaelis Complex of Aldoxime Dehydratase

inferredcites →https://doi.org/10.1074/jbc.m407681200openalex-snapshot

Desulfoglucosinolate Sulfotransferases from Arabidopsis thaliana Catalyze the Final Step in the Biosynthesis of the Glucosinolate Core Structure

inferredcites →https://doi.org/10.1074/jbc.m410474200openalex-snapshot

Regulation of Aldoxime Dehydratase Activity by Redox-dependent Change in the Coordination Structure of the Aldoxime-Heme Complex

inferredcites →https://doi.org/10.1074/jbc.m502332200openalex-snapshot

Elucidation of Gene-to-Gene and Metabolite-to-Gene Networks inArabidopsis by Integration of Metabolomics andTranscriptomics

inferredcites →https://doi.org/10.1104/pp.001263openalex-snapshot

Leucine-Derived Cyano Glucosides in Barley

inferredcites →https://doi.org/10.1104/pp.103.038059openalex-snapshot

Biosynthesis of the Nitrile Glucosides Rhodiocyanoside A and D and the Cyanogenic Glucosides Lotaustralin and Linamarin in Lotus japonicus

inferredcites →https://doi.org/10.1104/pp.110.164053openalex-snapshot

Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin in Cassava: Isolation, Biochemical Characterization, and Expression Pattern of CYP71E7, the Oxime-Metabolizing Cytochrome P450 Enzyme

inferredcites →https://doi.org/10.1104/pp.123.4.1437openalex-snapshot

Transgenic Tobacco and Arabidopsis Plants Expressing the Two Multifunctional Sorghum Cytochrome P450 Enzymes, CYP79A1 and CYP71E1, Are Cyanogenic and Accumulate Metabolites Derived from Intermediates in Dhurrin Biosynthesis

inferredcites →https://doi.org/10.1104/pp.127.1.108openalex-snapshot

The Involvement of Two P450 Enzymes, CYP83B1 and CYP83A1, in Auxin Homeostasis and Glucosinolate Biosynthesis

inferredcites →https://doi.org/10.1105/tpc.107.051383openalex-snapshot

ArabidopsisCytochrome P450 Monooxygenase 71A13 Catalyzes the Conversion of Indole-3-Acetaldoxime in Camalexin Synthesis

inferredcites →https://doi.org/10.1105/tpc.111.083998openalex-snapshot

Cytosolic γ-Glutamyl Peptidases Process Glutathione Conjugates in the Biosynthesis of Glucosinolates and Camalexin in Arabidopsis

inferredcites →https://doi.org/10.1105/tpc.113.118265openalex-snapshot

Two Herbivore-Induced Cytochrome P450 Enzymes CYP79D6 and CYP79D7 Catalyze the Formation of Volatile Aldoximes Involved in Poplar Defense

inferredcites →https://doi.org/10.1105/tpc.13.1.101openalex-snapshot

CYP83B1, a Cytochrome P450 at the Metabolic Branch Point in Auxin and Indole Glucosinolate Biosynthesis in Arabidopsis

inferredcites →https://doi.org/10.1105/tpc.7.9.1405openalex-snapshot

Superroot, a recessive mutation in Arabidopsis, confers auxin overproduction.

inferredcites →https://doi.org/10.1111/j.1365-313x.2011.04529.xopenalex-snapshot

A P450‐centric view of plant evolution

inferredcites →https://doi.org/10.1111/j.1365-313x.2011.04685.xopenalex-snapshot

Genomic clustering of cyanogenic glucoside biosynthetic genes aids their identification in Lotus japonicus and suggests the repeated evolution of this chemical defence pathway

inferredcites →https://doi.org/10.1111/j.1439-0418.2007.01177.xopenalex-snapshot

Olfactory response of a predatory mirid to herbivore induced plant volatiles: multiple herbivory vs. single herbivory

inferredcites →https://doi.org/10.1111/j.1467-7652.2011.00646.xopenalex-snapshot

A combined biochemical screen and TILLING approach identifies mutations in Sorghum bicolor L. Moench resulting in acyanogenic forage production

inferredcites →https://doi.org/10.1111/j.1742-4658.2011.08469.xopenalex-snapshot

Possible evolution of alliarinoside biosynthesis from the glucosinolate pathway in Alliaria petiolata

inferredcites →https://doi.org/10.1111/tpj.12541openalex-snapshot

Comparative analysis of A rabidopsis UGT 74 glucosyltransferases reveals a special role of UGT 74C1 in glucosinolate biosynthesis

inferredcites →https://doi.org/10.1111/tpj.12711openalex-snapshot

Herbivore‐induced poplar cytochrome P450 enzymes of the CYP 71 family convert aldoximes to nitriles which repel a generalist caterpillar

inferredcites →https://doi.org/10.1126/science.1062249openalex-snapshot

Resistance to an Herbivore Through Engineered Cyanogenic Glucoside Synthesis

inferredcites →https://doi.org/10.1126/science.1191634openalex-snapshot

Insects Betray Themselves in Nature to Predators by Rapid Isomerization of Green Leaf Volatiles

inferredcites →https://doi.org/10.1126/science.1194971openalex-snapshot

Dynamic Metabolons

inferredcites →https://doi.org/10.1128/aem.66.6.2290-2296.2000openalex-snapshot

Distribution of Aldoxime Dehydratase in Microorganisms

inferredcites →https://doi.org/10.1146/annurev-arplant-050213-040027openalex-snapshot

Cyanogenic Glycosides: Synthesis, Physiology, and Phenotypic Plasticity

inferredcites →https://doi.org/10.1146/annurev.arplant.57.032905.105228openalex-snapshot

BIOLOGY AND BIOCHEMISTRY OF GLUCOSINOLATES

inferredcites →https://doi.org/10.1186/gb-2000-1-6-reviews3003openalex-snapshot

Cytochromes P450: a success story.

inferredcites →https://doi.org/10.1186/s12870-015-0526-1openalex-snapshot

The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation

inferredcites →https://doi.org/10.1271/bbb.69.2254openalex-snapshot

Purification and Characterization of Aldoxime Dehydratase of the Head Blight Fungus,Fusarium graminearum

inferredcites →https://doi.org/10.2307/2446366openalex-snapshot

Parallel evolution of glucosinolate biosynthesis inferred from congruent nuclear and plastid gene phylogenies

inferredcites →https://doi.org/10.4161/psb.27640openalex-snapshot

Identification and characterization of CYP79D6v4, a cytochrome P450 enzyme producing aldoximes in black poplar (Populus nigra)

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Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Cyanogenic Glycosides and Biogenetically Related Compounds in Higher Plants and Animals

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The case for sporadic cyanogenic glycoside evolution in plants

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The CYP79A1 catalyzed conversion of tyrosine to (E)-p-hydroxyphenylacetaldoxime unravelled using an improved method for homology modeling

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Additional file 2 of Integrated pathway mining and selection of an artificial CYP79-mediated bypass to improve benzylisoquinoline alkaloid biosynthesis

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Biosynthesis and Role of Dhurrin in Forage Sorghum

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