Bioorganic Chemistry
A.Y. 2026/2027
Learning objectives
Aim of the course Is to illustrate how the principles of organic chemistry can be applied to the study of the reactions involved in metabolic processes. It provides knowledges about the fundamentals of enzymatic catalysis by illustrating the application of conceptual tools, experimental techniques and informatics tools to the study of enzyme-catalyzed reactions. Part of the course will be devoted to the use of enzymes for preparative purposes in organic synthesis.
Expected learning outcomes
Students will acquire knowledges about the most common enzymatic mechanisms used by Nature. Students will also be able to apply the already acquired knowledges in Organic Chemistry and the interdisciplinary tools from Bioorganic Chemistry in order to formulate hypothesis about an enzyme-catalyzed reaction and to propose experiments aimed at verifying the postulated hypotheses. Finally, students will acquire knowledge about the possible use of enzymes as catalysts in organic synthesis.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
Second semester
Course syllabus
Objectives and tools of Bioorganic Chemistry.
Structure and functions of enzymes: recapitulation on the structure of proteins; the active site.
Mechanisms in enzymatic catalysis.
Cofactors and coenzymes.
The IUBMB classification of enzymes.
Computer tools and online resources for the study of enzymes and bioorganic chemistry.
Application of the tools of Bioorganic Chemistry previously described through the case studies of:
- enzymatic group transfer reactions: hydrolysis, phosphorylation;
- biocatalyzed carbon-carbon bond forming and bond breaking reactions (aldol, Claisen and unpolung carbonyl condensations);
- reactions catalyzed by pyridoxalphosphate- and thiaminediphosphate-dependent enzymes;
- decarboxylations and carboxylations;
- oxidation-reduction reactions involving nicotinamide coenzymes; formal transfer of hydride ions.
- reactions catalyzed by flavin-dependent enzymes such as oxidases and oxygenases;
- reactions catalyzed by enzymes containing the heme group;
- biocatalyzed radical reactions.
Biocatalysis and biocatalyzed organic synthesis: main characteristics, advantages, and disadvantages; reaction media engineering; kinetic resolutions vs. asymmetric synthesis.
Application of the concepts of Bioorganic Chemistry and enzymatic catalysis in synthetic and retrosynthetic case studies of fine chemicals through enzymatic and chemo-enzymatic processes.
Structure and functions of enzymes: recapitulation on the structure of proteins; the active site.
Mechanisms in enzymatic catalysis.
Cofactors and coenzymes.
The IUBMB classification of enzymes.
Computer tools and online resources for the study of enzymes and bioorganic chemistry.
Application of the tools of Bioorganic Chemistry previously described through the case studies of:
- enzymatic group transfer reactions: hydrolysis, phosphorylation;
- biocatalyzed carbon-carbon bond forming and bond breaking reactions (aldol, Claisen and unpolung carbonyl condensations);
- reactions catalyzed by pyridoxalphosphate- and thiaminediphosphate-dependent enzymes;
- decarboxylations and carboxylations;
- oxidation-reduction reactions involving nicotinamide coenzymes; formal transfer of hydride ions.
- reactions catalyzed by flavin-dependent enzymes such as oxidases and oxygenases;
- reactions catalyzed by enzymes containing the heme group;
- biocatalyzed radical reactions.
Biocatalysis and biocatalyzed organic synthesis: main characteristics, advantages, and disadvantages; reaction media engineering; kinetic resolutions vs. asymmetric synthesis.
Application of the concepts of Bioorganic Chemistry and enzymatic catalysis in synthetic and retrosynthetic case studies of fine chemicals through enzymatic and chemo-enzymatic processes.
Prerequisites for admission
Successful attendance requires some basic knowledge from completing a bachelor's degree. A fundamental prerequisite is knowledge of the structure, properties, and reactivity of organic chemistry functional groups; knowledge of the chemistry of the main classes of biologically relevant compounds such as carbohydrates, amino acids, and peptides is recommended. These requirements should derive from the Organic Chemistry 1, 2 and 3 teachings of the Bachelor's Degree. Knowledge of acid-base theories, the foundations of stereochemistry, and the principles of chemical kinetics (teachings in General Chemistry, Organic Chemistry, and Physical Chemistry from the Bachelor's Degree) is also required. Knowledge of the basic biochemistry of proteins (primary, secondary, tertiary and quaternary structure and the concept of folding) and of the main metabolic pathways (teaching of Biological Chemistry from the Bachelor's Degree) is desirable. Knowledge of the most common spectroscopic techniques (UV-vis; IR; NMR; mass spectrometry) deriving from the courses in Analytical Chemistry and Instrumental Methods for Structural and Thermal Analysis of the Bachelor's Degree is useful but not essential.
Teaching methods
Traditional classroom lessons with the support of projected materials and explanations on the blackboard; teaching attendance is strongly recommended.
Teaching Resources
- TDH Bugg. Introduction to enzyme and coenzyme chemistry, Third Edition. Wiley, 2012.
For the use of enzymes as biocatalysts in organic synthesis:
- References to reviews and original articles are provided at the bottom of the illustrative material distributed through the Ariel teaching website.
For consultation:
- RB Silvermann. The organic chemistry of enzyme-catalyzed reactions. Academic Press, 2000.
- J. McMurry, T. Begley. Bio-organic chemistry. Zanichelli, 2007
The illustrative material used during the lessons will be made available through the Ariel site of the teaching.
For the use of enzymes as biocatalysts in organic synthesis:
- References to reviews and original articles are provided at the bottom of the illustrative material distributed through the Ariel teaching website.
For consultation:
- RB Silvermann. The organic chemistry of enzyme-catalyzed reactions. Academic Press, 2000.
- J. McMurry, T. Begley. Bio-organic chemistry. Zanichelli, 2007
The illustrative material used during the lessons will be made available through the Ariel site of the teaching.
Assessment methods and Criteria
Oral: the exam will consist of an interview that, starting from a topic covered in class, will develop subsequently so as to allow the evaluation of:
- degree of understanding and knowledge of the topics covered;
- properties of language and clarity of exposition;
- ability to connect between different topics;
- degree of mastery of the conceptual and experimental tools available to the bioorganic chemist;
- the candidate's ability to address issues different from those addressed in class based on the skills acquired.
- degree of understanding and knowledge of the topics covered;
- properties of language and clarity of exposition;
- ability to connect between different topics;
- degree of mastery of the conceptual and experimental tools available to the bioorganic chemist;
- the candidate's ability to address issues different from those addressed in class based on the skills acquired.
CHEM-05/A - Organic Chemistry - University credits: 6
Lessons: 48 hours
Professors:
Bassanini Ivan, Morelli Carlo
Shifts:
Professor(s)
Reception:
from Monday to Friday by appointment
Professor's office, Department of Chemistry.