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Pathway to Shikimic acid, Biosynthetic Precursors, Downstream Products.
Typology: Lecture notes
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Shikimic Acid Pathway and Aromatic Amino Acid Biosynthesis
1. Define : Pathway to shikimic acid , from which the aromatic amino acids Trp , Tyr , Phe are derived. 2. Why is it important? Why study this pathway? - among the essential amino acids we derive from our diet. Plants, microbes can synthesize them - biosynthetic precursors for bioactive secondary plant metabolites ( phenylpropanoids such as lignin,
flavonoids, some alkaloids)
popular and controversial herbicide acts on one enzyme of this pathway
3. Biosynthetic Precursors: - phospho-enol-pyruvat e (derived from glycolysis) - erythrose- 4 - phosphate (a 4C sugar, from oxidative pentose phosphate pathway) - nitrogen is derived from several other amino acids: glu , gln , **ser
i) DAHP synthase (3-deoxy-arabino-heptulosonate- 7 - phosphate = DAHP) (= entry point)
ii) EPSP synthase (enolpyruvyl shikimate- 3 - phospate)
iii) chorismate synthase (chorismate) )("fork" - branch point in the pathway)
iv) anthranilate synthase (branch specific for Trp)
v) chorismate mutase ( makes prephenate )
iv) glutamate prephenate aminotransferase (adds amino group, to make arogenate)
5. Localization : two locations for parallel pathways (although this is somewhat disputed) - chloroplast, functions to provide amino acids for protein synthesis - cytoplasmic, where Phe is required in large quantities for phenylpropanoid synthesis (lignin and
secondary metabolites)
6. Regulation depends on the downstream products
i) feedback control (allosteric) by end products:
Trp - inhibits anthranilate synthase , ups chorismate mutase Phe and Tyr downregulate chorismate mutase
Phe also downregulates arogenate dehydratase
Arogenate (intermediate) inibits DAHP synthase
ii) environmental control:
example 1: DAHP synthase and shikimate dehydrogenase are elicitor-induced
example 2: anthranilate synthases (AnS) in Ruta graveolen s, required for inducible defense chemicals
AnSa2 is trp - inhibited, but not elicitor-sensitive, AnSa1 is very elicitor-sensitive, but not trp - inhibited.
Why might different regulatory mechanism be important?
For Discussion:
Genetically engineered herbicide-resistant crops of various types are commonly used in modern 'industrial'
agriculture. Roundup Ready Canola is very common on the Canadian prairies, and is very popular among
growers. The benefits and costs or dangers have been discussed.
Do you think you have ingested any herbicide resistant plant products? Do you think or worry about it?
What are the benefits of herbicide resistant crops?
Do you see any obvious health risks?
What are the potential problems associated with herbicide resistant crops? What are the big environmental
issues, if any. Any agronomic problems?