Docsity
Docsity

Prepare for your exams
Prepare for your exams

Study with the several resources on Docsity


Earn points to download
Earn points to download

Earn points by helping other students or get them with a premium plan


Guidelines and tips
Guidelines and tips

Shikimic Acid Pathway and Aromatic Amino Acid Biosynthesis, Lecture notes of Organic Chemistry

Pathway to Shikimic acid, Biosynthetic Precursors, Downstream Products.

Typology: Lecture notes

2020/2021

Uploaded on 05/24/2021

lovefool
lovefool 🇬🇧

4.5

(21)

293 documents

1 / 4

Toggle sidebar

This page cannot be seen from the preview

Don't miss anything!

bg1
Shikimate)Pathway)2017)p.))
1
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))
-)example)amino)acid)pathway)for)synthesis)and)regulation)via)feedbacks)
-)case)study)of)agricultural)biotechnology)and)herbicide)resistant)plants:)Glyphosate)(Roundup),)a)very)
popular)and)controversial)herbicide)acts)on)one)enzyme)of)this)pathway)
)
3.''Biosynthetic'Precursors:'
) -)phospho-enol-pyruvate)(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)
)
'
4.''Key'enzymes'and'intermediates:)
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))
)
pf3
pf4

Partial preview of the text

Download Shikimic Acid Pathway and Aromatic Amino Acid Biosynthesis and more Lecture notes Organic Chemistry in PDF only on Docsity!

Shikimate Pathway 2017 p. 1

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)

  • example amino acid pathway for synthesis and regulation via feedbacks
  • case study of agricultural biotechnology and herbicide resistant plants: Glyphosate (Roundup), a very

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

  1. Key enzymes and intermediates:**

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:

  • light induces the chloroplast enzymes via thioredoxin
  • pest and pathogen attack triggers the cytoplasmic' shikimate pathway (specialized for phenylpropanoids)

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?