BIOORGANIC CHEMISTRY - MOD. 1

This course is part of the core activities of the Master’s Degree in Chemistry and Sustainable Technologies, curriculum Biomolecular Chemistry.

Learning Objectives
The course aims to provide students with both theoretical knowledge and practical skills necessary to understand and analyze organic processes of biological interest, integrating fundamental concepts of Organic Chemistry with the study of reactions occurring in living systems. Through lectures, students acquire theoretical concepts, while laboratory activities allow them to apply this knowledge in practice, developing experimental and analytical skills. The teaching approach also includes exercises, discussions, and group work to foster critical thinking and independent judgment. Assessment is based on written exams, oral examinations, and laboratory reports, ensuring a comprehensive and structured learning process.

By the end of the course, students will be able to:
• apply a chemical approach to the interpretation of biological reactions;
• critically compare organic reactions in biological systems with those typical of synthetic organic chemistry, highlighting similarities and differences in terms of reactivity and mechanisms;
• perform basic laboratory experiments involving biologically relevant organic compounds and/or biocatalysts;
• characterize the studied compounds in terms of structure, stereochemistry, and function;
• understand the reaction mechanisms associated with the studied biological systems.

Course Content
The course is structured into two modules, each including both theoretical lessons and practical laboratory activities. The lectures cover fundamental principles of organic reactivity in biological systems, while the lab sessions offer hands-on application of the acquired concepts, with particular focus on:
• organic reactions in biological contexts;
• use of biocatalysts;
• structural characterization techniques;
• study of stereochemical and biological properties of the compounds under investigation.

Knowledge and Understanding
At the end of the course, students are expected to:
• demonstrate a solid understanding of the fundamental concepts of organic chemistry, with particular reference to the main reaction pathways and supramolecular interactions underlying the chemical processes occurring in living systems;
• recognize the main classes of biological and biomimetic reactions, as well as the key chemical interactions (both covalent and non-covalent) that govern their mechanisms;
• understand the principles of organic reactivity that drive the functioning of biological systems and underpin the design of biomimetic systems.

Applying Knowledge and Understanding
Students will be able to:
• appropriately and flexibly apply the acquired knowledge to analyze and represent biosynthetic and biomimetic reactions using standard chemical notation and symbols;
• translate theoretical knowledge into practical skills through laboratory experiments involving biologically relevant reactions, including: a) monitoring reaction progress, b) developing methods for quantification and purification of biologically derived compounds, c) determining the regioselectivity and stereoselectivity of enzymatic reactions, d) performing key biochemical transformations using synthetic biomimetic catalysts.

Autonomy of Judgment
Students will develop critical thinking skills and will be expected to:
• identify and articulate meaningful correlations between the reactivity of organic compounds and biological systems;
• apply these correlations to solve practical problems in the laboratory and to contribute to the conceptual development of biomimetic systems.

Communication Skills
Upon successful completion of the course, students will be able to:
• use chemical terminology and notation appropriately and effectively;
• engage actively and constructively in discussions with peers and instructors, both during lectures and laboratory sessions;
• communicate experimental procedures and results with clarity, precision, and chemical relevance, using concise and scientifically accurate language;
• collaborate effectively within laboratory groups, maintaining a high level of focus and scientific rigor throughout all experimental activities.

Learning Skills
Students are expected to:
• take structured and meaningful notes, highlighting key concepts and organizing content by relevance;
• integrate course materials with their own notes in a coherent and comprehensive manner;
• critically discuss course topics, both in written and oral form, using appropriate and effective arguments;
• accurately record experimental results and observations (including macroscopic and chromatic changes) and relate them to theoretical concepts and laboratory instructions;
• write concise yet comprehensive group laboratory reports (a few pages in length), clearly presenting the objective of the experiment, the collected data, and the related discussion.

To ensure a full understanding of the laboratory module, it is strongly recommended that students have already acquired the learning outcomes of the fundamental courses in Organic Chemistry and Biochemistry. In particular, students are expected to be familiar with:
• the reactivity of major functional groups;
• the physicochemical properties of mono- and polyfunctional organic compounds;
• the main classes of biologically relevant molecules and their role in primary metabolism.
It is therefore advisable that students have successfully completed Organic Chemistry I, Organic Chemistry II, and Biochemistry, or possess equivalent knowledge and skills.

The course covers the following main topics:
• Functional groups in biological chemistry
• Prebiotic chemistry
• Weak interactions and their role in biological systems
• Molecular self-assembly
• Stereochemistry of biological molecules
• Reactivity of monosaccharides
• Enzyme nomenclature and classification
• Enzyme activity and enzyme kinetics
• General and specific acid/base catalysis
• Introduction to laboratory experiences
• Analysis and interpretation of experimental data

Additionally, three laboratory sessions are scheduled, totaling 18 hours and divided into three separate sessions. Laboratory activities attendance is mandatory.
• Experiment 1: Study of glucose mutarotation using NMR analysis;
• Experiment 2: Applications of supramolecular chemistry: cyclodextrins as complexing agents;
• Experiment 3: Structural characterization of a dipeptide using mono- and bi-dimensional NMR analysis.

Richard B. Smith “Biochemistry. An Organic Chemistry Approach” CRC Press, 2020, ISBN: 978-0-8153-6713-0
David Van Vraken, Gregory A. Weiss "Introduction to Bioorganic Chemistry and Chemical Biology" Garland Science, 2012, ISBN: 978-0-8153-4214-4

The assessment is common to both modules of the course and is structured in several stages, aimed at evaluating both the theoretical knowledge and the practical skills acquired by students.
A single written exam lasting 2 hours is scheduled, consisting of multiple-choice and open-ended questions, designed to assess the understanding of the topics covered in the theoretical modules.
Passing the written exam with a minimum score of 18/30 is required to access the oral exam, during which:
• students’ understanding and critical analysis of theoretical topics will be assessed;
• the laboratory experiences carried out will be discussed;
• the group laboratory reports will be evaluated.
The assessment of the laboratory activities will be based on:
• active and informed participation in experimental activities (attendance is mandatory);
• the ability to process and discuss the experimental data obtained;
• the preparation of group laboratory reports, presenting clearly, concisely, and scientifically the objectives, methods, results, and their interpretation.
The submission of laboratory reports is a mandatory prerequisite for admission to both the written and oral exams.

written and oral

The final grade for the course is expressed on a scale of 30 and is determined by a weighted average of the different assessment components, as follows:
• 70%: average of the written and oral exams, which assess theoretical knowledge, critical understanding of the content, and mastery of scientific language;
• 30%: evaluation of laboratory activities, based on active participation, processing of experimental data, and the quality of laboratory reports.
To pass the course, students must achieve a satisfactory evaluation in both components (theoretical exam and laboratory work). The final grade reflects not only the acquisition of theoretical content, but also the development of practical skills and transversal competences acquired during the course.

The course combines theoretical lectures with practical laboratory sessions, aimed at integrating conceptual knowledge with experimental skills.
• Lectures: Delivered in a traditional format, these sessions are focused on presenting the theoretical foundations of the course and introducing the experimental techniques used in the laboratory.
• Laboratory activities: The course includes 18 hours of hands-on laboratory work, divided into multiple sessions and held at the Organic Chemistry Teaching Laboratory (Beta Building, 1st floor). These sessions are preceded by introductory theoretical lessons that present the experimental procedures and provide a concise overview of the analytical techniques involved.
• Safety training: At the beginning of the first laboratory session, the main individual and collective safety regulations will be reviewed, with emphasis on the proper use of personal protective equipment and the safe handling of chemical substances.
• Learning materials: All course materials will be made available on the university’s Moodle platform, including PDF copies of the lecture slides, experimental protocols for the lab sessions, and data files collected during the experiments.
• Self-assessment: To support reflective learning and help students monitor their progress, a series of anonymous self-assessment quizzes (via Socrative) will be administered during the course and discussed in class.
• Active learning: The course also includes group-based activities such as problem solving, bibliographic research, and flipped classroom sessions, designed to foster student engagement, critical thinking, and independent learning.

Accessibility, Disability and Inclusion

Accommodations and Support Services for students with disabilities or with specific learning disabilities:
Ca 'Foscari applies Italian law (Law 17/1999; Law 170/2010) for support and accommodation services available to students with disabilities or with specific learning disabilities. In case of motor, visual, hearing or other disabilities (Law 17/1999) or a specific learning disorder (Law 170/2010) and you need support (classroom assistance, technological aids for carrying out exams or individualized exams, material in accessible format, recovery of notes, specialized tutoring to support the study, interpreters or other), contact the Disability and SLD office. disabilita@unive.it.