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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Pathway: dhurrin biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Nitrogen-Containing Secondary Compounds Biosynthesis Nitrogen-Containing Glucosides Biosynthesis Cyanogenic Glucosides Biosynthesis

Some taxa known to possess this pathway include ? : Sorghum bicolor

Expected Taxonomic Range: Magnoliophyta

Summary:
Dhurrin is a cyanogenic glucoside produced by seedlings of Sorghum bicolor. It functions as a plant defense compound. [Celenza01, Jones99]


References

Celenza01: Celenza JL (2001). "Metabolism of tyrosine and tryptophan--new genes for old pathways." Curr Opin Plant Biol 2001;4(3);234-40. PMID: 11312134

Jones99: Jones PR, Moller BL, Hoj PB (1999). "The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity." J Biol Chem 1999;274(50);35483-91. PMID: 10585420

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bairoch93a: Bairoch A, Boeckmann B (1993). "The SWISS-PROT protein sequence data bank, recent developments." Nucleic Acids Res. 21:3093-3096. PMID: 8332529

Bak98: Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA (1998). "Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin." Plant Mol Biol 36(3);393-405. PMID: 9484480

Busk02: Busk PK, Moller BL (2002). "Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants." Plant Physiol 129(3);1222-31. PMID: 12114576

Halkier90: Halkier BA, Moller BL (1990). "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." J Biol Chem 265(34);21114-21. PMID: 2250015

Hosel80: Hosel W, Nahrstedt A (1980). "In vitro biosynthesis of the cyanogenic glucoside taxiphyllin in Triglochin maritima." Arch Biochem Biophys 203(2);753-7. PMID: 7458352

Kahn97b: Kahn RA, Bak S, Svendsen I, Halkier BA, Moller BL (1997). "Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum." Plant Physiol 1997;115(4);1661-70. PMID: 9414567

Kahn99: Kahn RA, Fahrendorf T, Halkier BA, Moller BL (1999). "Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench." Arch Biochem Biophys 1999;363(1);9-18. PMID: 10049494

Koch95: Koch BM, Sibbesen O, Halkier BA, Svendsen I, Moller BL (1995). "The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench." Arch Biochem Biophys 1995;323(1);177-86. PMID: 7487064

Kristensen05: Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S (2005). "Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome." Proc Natl Acad Sci U S A 102(5);1779-84. PMID: 15665094

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

MacFarlane75: MacFarlane IJ, Lees EM, Conn EE (1975). "The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor." J Biol Chem 250(12);4708-13. PMID: 237909

Nielsen00: Nielsen JS, Moller BL (2000). "Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima." Plant Physiol 122(4);1311-21. PMID: 10759528

Nielsen99: Nielsen JS, Moller BL (1999). "Biosynthesis of cyanogenic glucosides in Triglochin maritima and the involvement of cytochrome P450 enzymes." Arch Biochem Biophys 368(1);121-30. PMID: 10415119

Reay74: Reay PF, Conn EE (1974). "The purification and properties of a uridine diphosphate glucose: aldehyde cyanohydrin beta-glucosyltransferase from sorghum seedlings." J Biol Chem 1974;249(18);5826-30. PMID: 4416442

Shimada77: Shimada M, Conn EE (1977). "The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile." Arch Biochem Biophys 180(1);199-207. PMID: 193443

Sibbesen94: Sibbesen O, Koch B, Halkier BA, Moller BL (1994). "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." Proc Natl Acad Sci U S A 1994;91(21);9740-4. PMID: 7937883

Sibbesen95: Sibbesen O, Koch B, Halkier BA, Moller BL (1995). "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." J Biol Chem 1995;270(8);3506-11. PMID: 7876084

Thorsoe05: Thorsoe KS, Bak S, Olsen CE, Imberty A, Breton C, Lindberg Moller B (2005). "Determination of catalytic key amino acids and UDP sugar donor specificity of the cyanohydrin glycosyltransferase UGT85B1 from Sorghum bicolor. Molecular modeling substantiated by site-specific mutagenesis and biochemical analyses." Plant Physiol 139(2);664-73. PMID: 16169969


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Dec 21, 2014, BIOCYC13A.