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N Use By Plants
Nitrate Assimilation
Ammonia Assimilation
Glu, Gln, Asn, Gly, Ser
Aminotransferases
Asp, Ala, GABA
Val, Leu, Ileu, Thr, Lys
Pro, Arg, Orn
Polyamines
Non-protein AAs
Alkaloids
Sulfate Assimilation
Cys, Met, AdoMet, ACC
His, Phe, Tyr, Tryp
Secondary Products
Onium Compounds
Enzymes
Methods
Simulation
References
HORT640 - Metabolic Plant Physiology

References, DAHP or heptulosonate

Ahmad S, Jensen RA. The phylogenetic origin of the bifunctional tyrosine-pathway protein in the enteric lineage of bacteria. Mol. Biol. Evol. 5: 282-297 (1988).

Akowski JP, Bauerle R. Steady-state kinetics and inhibitor binding of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (tryptophan sensitive) from Escherichia coli. Biochemistry 36: 15817-15822 (1997).

Balderas-Hernandez VE, Sabido-Ramos A, Silva P, Cabrera-Valladares N, Hernandez-Chavez G, Baez-Viveros JL, Martinez A, Bolívar F, Gosset G. Metabolic engineering for improving anthranilate synthesis from glucose in Escherichia coli. Microb. Cell Fact. 8: 19 (2009).

Berry A, Ahmad S, Liss A, Jensen RA. Enzymological features of aromatic amino acid biosynthesis reflect the phylogeny of mycoplasmas. J. Gen. Microbiol. 133: 2147-2154 (1987).

Berry A, Jensen RA, Hendry AT. Enzymic arrangement and allosteric regulation of the aromatic amino acid pathway in Neisseria gonorrhoeae. Arch. Microbiol. 149: 87-94 (1987).

Bischoff M, Schaller A, Bieri F, Kessler F, Amrhein N, Schmid J. Molecular characterization of tomato 3-dehydroquinate dehydratase-shikimate:NADP oxidoreductase. Plant Physiol. 125: 1891-1900 (2001).

Byng GS, Berry A, Jensen RA. Evolutionary implications of features of aromatic amino acid biosynthesis in the genus Acinetobacter. Arch. Microbiol. 143: 122-129 (1985).

Byng GS, Whitaker RJ, Shapiro CL, Jensen RA. The aromatic amino acid pathway branches at L-arogenate in Euglena gracilis. Mol. Cell Biol. 1: 426-438 (1981).

Cameron DC, Chaplen FW. Developments in metabolic engineering. Curr. Opin. Biotechnol. 8: 175-80 (1997).

Chen CC, Liao CC, Hsu WH. The cloning and nucleotide sequence of a Corynebacterium glutamicum 3-deoxy-D-arabinoheptulosonate-7-phosphate synthase gene. FEMS Microbiol. Lett. 107: 223-229 (1993).

Dyer WE, Weaver LM, Zhao JM, Kuhn DN, Weller SC, Herrmann KM. A cDNA encoding 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Solanum tuberosum L. J. Biol. Chem. 265: 1608-1614 (1990).

Entus R, Poling M, Herrmann KM. Redox regulation of Arabidopsis 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase. Plant Physiol. 129: 1866-1871 (2002).

Fiske MJ, Kane JF. Regulation of phenylalanine biosynthesis in Rhodotorula glutinis. J. Bacteriol. 160: 676-681 (1984).

Fiske MJ, Whitaker RJ, Jensen RA. Hidden overflow pathway to L-phenylalanine in Pseudomonas aeruginosa. J. Bacteriol. 154: 623-631 (1983).

Flores N, Xiao J, Berry A, Bolivar F, Valle F. Pathway engineering for the production of aromatic compounds in Escherichia coli. Nat. Biotechnol. 14: 620-623 (1996).

Forlani G. Properties of the 5-enol-pyruvyl-shikimate-3-phosphate synthase isoforms isolated from maize cultured cells. J. Plant Physiol. 150: 369-375 (1997).

Forlani G, Kafarski P, Lejczak B, Boduszek B, Gancarz R, Torreilles C, Soloducho J, Wojtasek H, Hafner J, Korf J, Wieczorek P. Herbicidally active derivatives of aminomethylenebisphosphonic acid: mode of action and structure - activity relationship. Phosphorus Sulfur Silicon Relat. Elem. 110: 353-356 (1996).

Forlani G, Lejczak B, Kafarski P. The herbicidally active compound N-2-(6-methyl-pyridyl)- aminomethylene bisphosphonic acid inhibits in vivo aromatic biosynthesis. J. Plant Growth Regul. 18: 73-79 (1999).

Forlani G, Lejczak B, Kafarski P. N-pyridyl-aminomethylene-bisphosphonic acids inhibit the first enzyme in the shikimate pathway, 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase. Pest. Biochem. Physiol. 55: 180-188 (1996).

Forlani G, Lejczak B, Kafarski P. The herbicidally active compound N-2-(5-chloro-pyridyl) aminomethylene bisphosphonic acid acts by inhibiting both glutamine and aromatic amino acid biosynthesis. Aust. J. Plant Physiol. 27: 677-683 (2000).

Fukuda K, Watanabe M, Asano K, Ouchi K, Takasawa S. A mutated ARO4 gene for feedback-resistant DAHP synthase which causes both o-fluoro-DL-phenylalanine resistance and beta-phenethyl-alcohol overproduction in Saccharomyces cerevisiae. Curr. Genet. 20: 453-456 (1991).

Furdui C, Zhou L, Woodard RW, Anderson KS. Insights into the mechanism of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (DAHP synthase) (Phe) from E. coli using a transient kinetic analysis. J. Biol. Chem. 279: 45618-45625 (2004).

Ger YM, Chen SL, Chiang HJ, Shiuan D. A single Ser-180 mutation desensitizes feedback inhibition of the phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthetase in Escherichia coli. J. Biochem. (Tokyo) 116: 986-990 (1994).

Gorlach J, Beck A, Henstrand JM, Handa AK, Herrmann KM, Schmid J, Amrhein N. Differential expression of tomato (Lycopersicon esculentum L.) genes encoding shikimate pathway isoenzymes. I. 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase. Plant Mol. Biol. 23: 697-706 (1993).

Gorlach J, Raesecke HR, Rentsch D, Regenass M, Roy P, Zala M, Keel C, Boller T, Amrhein N, Schmid J. Temporally distinct accumulation of transcripts encoding enzymes of the prechorismate pathway in elicitor-treated, cultured tomato cells. Proc. Natl. Acad. Sci. U.S.A. 92: 3166-3170 (1995).

Gorlach J, Schmid J, Amrhein N. Abundance of transcripts specific for genes encoding enzymes of the prechorismate pathway in different organs of tomato (Lycopersicon esculentum L.) plants. Planta 193: 216-223 (1994).

Hall GC, Flick MB, Gherna RL, Jensen RA. Biochemical diversity for biosynthesis of aromatic amino acids among the cyanobacteria. J. Bacteriol. 149: 65-78 (1982).

Hartmann M, Heinrich G, Braus GH. Regulative fine-tuning of the two novel DAHP isoenzymes aroFp and aroGp of the filamentous fungus Aspergillus nidulans. Arch. Microbiol. 175: 112-121 (2001).

Janzik I, Preiskowski S, Kneifel H. Ozone has dramatic effects on the regulation of the prechorismate pathway in tobacco (Nicotiana tabacum L. cv. Bel W3). Planta 223: 20-27 (2005).

Jelesko JG, Lara JC, Leigh JA. Rhizobium meliloti mutants with decreased DAHP synthase activity are sensitive to exogenous tryptophan and phenylalanine and form ineffective nodules. Mol. Plant Microbe Interact. 6: 135-143 (1993).

Keith B, Dong XN, Ausubel FM, Fink GR. Differential induction of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase genes in Arabidopsis thaliana by wounding and pathogenic attack. Proc. Natl. Acad. Sci. U.S.A. 88: 8821-8825 (1991).

Kikuchi Y, Tsujimoto K, Kurahashi O. Mutational analysis of the feedback sites of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase of Escherichia coli. Appl. Environ. Microbiol. 63: 761-762 (1997).

Knaggs AR. The biosynthesis of shikimate metabolites. Nat. Prod. Rep. 18: 334-355 (2001).

Koll P, Bode R, Birnbaum D. Regulation of metabolic branch points of aromatic amino acid biosynthesis in Pichia guilliermondii. J. Basic Microbiol. 28: 619-627 (1988).

Kunzler M, Paravicini G, Egli CM, Irniger S, Braus GH. Cloning, primary structure and regulation of the ARO4 gene, encoding the tyrosine-inhibited 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Saccharomyces cerevisiae. Gene 113: 67-74 (1992).

Liu YJ, Li PP, Zhao KX, Wang BJ, Jiang CY, Drake HL, Liu SJ. Corynebacterium glutamicum contains 3-deoxy-D-arabino-heptulosonate 7-phosphate synthases that display novel biochemical features. Appl. Environ. Microbiol. 74: 5497-5503 (2008).

Logemann E, Tavernaro A, Schulz W, Somssich IE, Hahlbrock K. UV light selectively coinduces supply pathways from primary metabolism and flavonoid secondary product formation in parsley. Proc. Natl. Acad. Sci. U.S.A. 97: 1903-1907 (2000).

Luttik MA, Vuralhan Z, Suir E, Braus GH, Pronk JT, Daran JM. Alleviation of feedback inhibition in Saccharomyces cerevisiae aromatic amino acid biosynthesis: quantification of metabolic impact. Metab. Eng. 10: 141-153 (2008).

McCue KF, Conn EE. Induction of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase activity by fungal elicitor in cultures of Petroselinum crispum. Proc. Natl. Acad. Sci. U.S.A. 86: 7374-7377 (1989).

Mori T, Sakurai M, Sakuta M. Effects of conditioned medium on activities of PAL, CHS, DAHP synthase (DS-Co and DS-Mn) and anthocyanin production in suspension cultures of Fragaria ananassa. Plant Sci. 160: 355-360 (2001).

Nimmo GA, Coggins JR. The purification and molecular properties of the tryptophan-sensitive 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Neurospora crassa. Biochem. J. 197: 427-436 (1981).

Oldiges M, Kunze M, Degenring D, Sprenger GA, Takors R. Stimulation, monitoring, and analysis of pathway dynamics by metabolic profiling in the aromatic amino acid pathway. Biotechnol. Prog. 20: 1623-1633 (2004).

Park OK, Bauerle R. Metal-catalyzed oxidation of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli: inactivation and destabilization by oxidation of active-site cysteines. J. Bacteriol. 181: 1636-1642 (1999).

Pereira SA, Livi GP. Aromatic amino-acid biosynthesis in Candida albicans: identification of the ARO4 gene encoding a second DAHP synthase. Curr. Genet. 29: 441-445 (1996).

Pereira SA, Livi GP. Cloning and expression of the ARO3 gene encoding DAHP synthase from Candida albicans. Gene 132: 159-165 (1993).

Ramilo CA, Evans JN. Overexpression, purification, and characterization of tyrosine-sensitive 3-deoxy-D-arabino-heptulosonic acid 7-phosphate synthase from Escherichia coli. Protein Expr. Purif. 9: 253-261 (1997).

Ray JM, Bauerle R. Purification and properties of tryptophan-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli. J. Bacteriol. 173: 1894-1901 (1991).

Schmitz M, Hirsch E, Bongaerts J, Takors R. Pulse experiments as a prerequisite for the quantification of in vivo enzyme kinetics in aromatic amino acid pathway of Escherichia coli. Biotechnol. Prog. 18: 935-941 (2002).

Schnappauf G, Hartmann M, Kunzler M, Braus GH. The two 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase isoenzymes from Saccharomyces cerevisiae show different kinetic modes of inhibition. Arch. Microbiol. 169: 517-524 (1998).

Schneider TR, Hartmann M, Braus GH. Crystallization and preliminary X-ray analysis of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (tyrosine inhibitable) from Saccharomyces cerevisiae. Acta Crystallogr. D. Biol. Crystallogr. 55: 1586-1588 (1999).

Shiio I, Sugimoto S. Altered prephenate dehydratase in phenylalanine-excreting mutants of Brevibacterium flavum. J. Biochem. (Tokyo) 79: 173-183 (1976).

Shiio I, Sugimoto S. Two components of chorismate mutase in Brevibacterium flavum. J. Biochem. (Tokyo) 86: 17-25 (1979).

Shumilin IA, Kretsinger RH, Bauerle RH. Crystal structure of phenylalanine-regulated 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli. Structure Fold. Des. 7: 865-875 (1999).

Simpson RJ, Davidson BE. Studies on 3-deoxy-D-arabinoheptulosonate-7-phosphate synthetase(phe) from Escherichia coli K12. 2. Kinetic properties. Eur. J. Biochem. 70: 501-507 (1976).

Simpson RJ, Davidson BE. Studies on 3-deoxy-D-arabinoheptulosonate-7-phosphate synthetase(phe) from Escherichia coli K12. 1. Purification and subunit structure. Eur. J. Biochem. 70: 493-500 (1976).

Stephens CM, Bauerle R. Essential cysteines in 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli. Analysis by chemical modification and site-directed mutagenesis of the phenylalanine-sensitive isozyme. J. Biol. Chem. 267: 5762-5767 (1992).

Stephens CM, Bauerle R. Analysis of the metal requirement of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli. J. Biol. Chem. 266: 20810-20817 (1991).

Stuart F, Hunter IS. Purification and characterization of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Streptomyces rimosus. Biochim. Biophys. Acta 1161: 209-215 (1993).

Subramaniam P, Bhatnagar R, Hooper A, Jensen RA. The dynamic progression of evolved character states for aromatic amino acid biosynthesis in gram-negative bacteria. Microbiology 140: 3431-3440 (1994).

Sugimoto S, Shiio I. Purification and properties of dissociable chorismate mutase from Brevibacterium flavum. J. Biochem. (Tokyo) 88: 167-176 (1980).

Sundaram AK, Howe DL, Sheflyan GY, Woodard RW. Probing the potential metal binding site in Escherichia coli 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (phenylalanine-sensitive). FEBS Lett. 441: 195-199 (1998).

Tribe DE, Pittard J. Hyperproduction of tryptophan by Escherichia coli: genetic manipulation of the pathways leading to tryptophan formation. Appl. Environ. Microbiol. 38: 181-190 (1979).

Wagner T, Shumilin IA, Bauerle R, Kretsinger RH. Structure of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli: comparison of the Mn(2+)*2-phosphoglycolate and the Pb(2+)*2-phosphoenolpyruvate complexes and implications for catalysis. J. Mol. Biol. 301: 389-399 (2000).

Walker GE, Dunbar B, Hunter IS, Nimmo HG, Coggins JR. Evidence for a novel class of microbial 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase in Streptomyces coelicolor A3(2), Streptomyces rimosus and Neurospora crassa. Microbiology 142: 1973-1982 (1996).

Whitaker RJ, Berry A, Byng GS, Fiske MJ, Jensen RA. Clues from Xanthomonas campestris about the evolution of aromatic biosynthesis and its regulation. J. Mol. Evol. 21: 139-149 (1984).

Yu TW, Muller R, Muller M, Zhang X, Draeger G, Kim CG, Leistner E, Floss HG. Mutational analysis and reconstituted expression of the biosynthetic genes involved in the formation of 3-amino-5-hydroxybenzoic acid, the starter unit of rifamycin biosynthesis in Amycolatopsis mediterranei S699. J. Biol. Chem. 276: 12546-12555 (2001).

Zhao J, Weaver LM, Herrmann KM. Translocation of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase precursor into isolated chloroplasts. Planta 216: 180-186 (2002).

Number of references = 67

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