Secondary Metabolism

Code:

Q0325

Acronym:

Q0325

Keywords
Classification	Keyword
OFICIAL	Chemistry

Instance: 2011/2012 - 1S

Active?	Yes
Web Page:	http://elearning2.fc.up.pt/aulasweb0910/course/view.php?id=2355
Responsible unit:	Department of Chemistry and Biochemistry
Course/CS Responsible:	Bachelor in Biochemistry

Cycles of Study/Courses

Acronym	No. of Students	Study Plan	Curricular Years	Credits UCN	Credits ECTS	Contact hours	Total Time
L:BQ	12	Plano de Estudos a partir de 2007	3	-	5	56	135

Teaching language

Portuguese

Objectives

This course fits in the basic formation of a biochemistry degree.
The living organisms, plants, bacteria, fungi, liquens, insects and animals, all produce an impressive array of compounds, with very diverse structures, which have enormous importance not only to the producers but also to mankind and are an immense reservoir of chemical diversity. Within this perspective and with the goal of complementing the knowledge acquired in passed years, we intend that the students have a basic knowledge about the different biogenetic pathways (acetate, mevalonate, non-mevalonate, shikimate…) linked to the production of natural products, their evolution and regulation as well as their integration with the basic or primary metabolism.
Following this premises our aims are that by the end of this course the students:
-Understand the key biosynthetic pathways for the biosynthesis of natural products,
-Recognise and be able to apply key biosynthetic reactions in order to predict how organisms make secondary metabolites,
-Understand the biological significance of secondary metabolites,
-Be able to work in natural product field,
-Have a better understanding of how works the inter- and intra-species relationships and their ecological importance.

Program

Part I – Secondary Metabolism Biosynthetic Pathways.
1. Secondary Metabolites derived from Acetate – Polyketides
1.1 – Relationship between Fatty Acids and Polyketides Biosynthetic Pathways.
1.1.1 - Fatty Acid Synthases (FAS) versus Polyketide Synthases (PKS).
1.1.2 - Processive and Iterative Type of Activity.
1.1.3 - Macrolides: Erythromycin.
1.2 – Polyphenolic Compounds Biosynthesis.
1.2.1 - Cyclization of linear polyketides: Polyphenols Formation.
1.2.2 - 4 C2 units: 6-Methylsalicilic acid (6-MSA)
1.2.3 - 5 C2 units: Citrinine.
1.2.4 - 6 C2 units: Naphthoquinones.
1.2.5 - 7 C2 units.
1.2.6 - 8 C2 units: Anthraquinones.
1.2.1 - Phenolic Oxidative Coupling. Usnic Acid.
1.3 – Oxidative Cleavage of Aromatic Rings.
1.4 – Methodologies to Study the Secondary Metabolites Biosynthesis.
2. Isoprenoids - Mevalonate and Non-Mevalonate Pathways
2.1 - Isoprene Rule and Terpenoid Classification.
2.2 – Mevalonate Pathway. Enzymes and their characteristics.
2.3 - Non-Mevalonate Pathway. Enzimes and their characteristics.
2.4 - IPP/DMAPP Isomerization. Diversity in the IPP/DMAPP Biosynthesis.
2.5 - Different Terpene Classes Biosynthesis. Enzymes and their characteristics.
2.5.1 – Hemiterpenes.
2.5.2 – Monoterpenes.
2.5.3 – Sesquiterpenes and Sesquiterpene Lactones.
2.5.4 – Diterpenes.
3. Shikimate Biosyntetic Pathway
3.1 - Biosynthetic Pathway to Amino acids Phenylalanine and Tirosine. Enzymes, their reactions e characteristics.
3.2 – Metabolites derivated from Phenylalanine. Enzymes, their reactions e characteristics.
3.2.1 – Phenylpropanoids.
3.2.2 – Lignins
3.2.3 – Lignans
3.2.4 – Coumarins
3.3 – Mixed Biosyntetic pathway Shiquimate-Acetate.
3.3.1 – Flavonoids
3.3.2 – Xantones
3.3.3 – Stilbenes
4. Alkaloids Biosynthetic Pathways
4.1 - Introduction
4.2 – Alkaloids Derived from Metabolism of Ornithine and Lysine
4.2.1 Pyrrolidine and Piperidine Alkaloids
4.2.1.1 – Hyoscyamine and scopolamine
4.2.1.2 – Cocaine
4.2.2 - Pyrrolizidíne and Quinolizidíne Alkaloids
4.2.3 – Pyridine Alkaloids
4.3 – Alkaloids Derived from Metabolism of Phenylalanine and Tyrosine
4.3.1 – Simple Monocyclic
4.3.2 – Isoquinolines
4.3.3 – Benzylisoquinolines and bis-benzylisoquinolines
4.3.4 – Amaryllidaceae Alkaloids
Parte II – General Aspects from the Secondary Metabolism (6 hours)
5. Primary and Secondary Metabolism
5.1 - Introduction
5.2 - Intermediary/Primary Metabolism
5.3 - Secondary Metabolism
6. Secondary Metabolites distinguishing characteristics
6.1 – Structural Diversity
6.2 – Accumulation of Secondary Metabolites
7. Secondary Metabolism Enzymology
7.1 – Plasticity of Reaction Pathways
7.2 - Enzyme Efficiency
7.3 – Enzyme Recruitment
7.4 – Induction and Regulation
8 - Shunt and Overflow Metabolism
Part III – Teorical - Practical Classes
9 - Strategies used to obtain Bioactive Natural Products. Isolation and Structural elucidation methods.
10 - Exercise resolution about biosynthetic mechanisms in the different pathways.
11 - Student Presentation of seminars according several themes such as: Ecological Biochemistry, Combinatorial Biosynthesis, Secondary Metabolites in Therapeutics.

Mandatory literature

Ana M. Lobo, Ana M. Lourenço; Biossíntese de Produtos Naturais, IST Press, 2007. ISBN: 978-972-8469-50-4
Natural Product Reports, Royal Society of Chemistry

Software

ChemSketch 12.0

Evaluation Type

Distributed evaluation with final exam

Assessment Components

Description	Type	Time (hours)	Weight (%)	End date
Attendance (estimated)	Participação presencial	60,00
	Total:	-	0,00

Eligibility for exams

According with the current regulations.

Calculation formula of final grade

Students are allowed to choose whether they wish to be evaluated through a single final exam or via two parcial exams.

For those who have chosen to be evaluated though a single final exam, their grade will be the grade obtained in this exam.

For those who have chosen to be evaluated via two parcial exams their grade will be the average of these two exams.

Examinations or Special Assignments

Are not provided

Special assessment (TE, DA, ...)

According with the current regulations.

Classification improvement

According with the current regulations.

Observations

Are recommended pre-requisites some knowledgement in General Chemistry, Physical Chemistry, Organic Chemistry and, above all, Biochemistry.