Structure and Functions of Biomolecules
A.Y. 2024/2025
Learning objectives
The aim of the course is an in-depth discussion of the structure-property and structure-activity relationships of the main classes of biomolecules of particular interest for the agri-food sector. Green and sustainable chemical strategies for their recovery, valorisation and transformation in value-added compounds will be also presented and discussed, together with relevant application for bioeconomy. Main spectroscopic techniques (UV and NMR) for chemical structural analysis will be presented.
Expected learning outcomes
The student will be able to critically discuss the structure-property and structure-activity relationships of biomolecules of particular interest for the agri-food sector. He will also acquire knowledge and skills on the most important extraction, preparation/purification, and transformation techniques with emphasis on green and sustainable methodologies. Students will be able to use combined UV and NMR spectroscopic data to assign and discuss the molecular structures of simple bioactive compounds. Finally, the student will be able to use the main experimental and computational methodologies for understanding the interactions of bioactives with macromolecules.
Lesson period: First 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
First semester
Course syllabus
Lessons: Amino acids and peptides. Structure and properties of amino acids and peptides. Nitrogen protecting groups: insertion and removal. Possible secondary reactions. Protecting groups of carboxylic and hydroxyl groups. Methods for activation and coupling. Possible racemization phenomena and mechanisms. Methods of solid phase synthesis. Resins and cleavage conditions. Fundamentals of Amino acid biosynthesis and metabolism. Amino acids as biosynthetic precursors. Primary structure determination of proteins. (1.5 CFU)
Carbohydrates. Structure, properties, nomenclature. Anomeric effect. Oxidation and reduction reactions. Glycosylation reactions: concept of glycosyl donor and glycosyl acceptor, promoters, protecting groups. Chemo-enzymatic synthesis of glycosidic bond. Oligosaccharide and glycoconjugates synthesis on solid phase. Structural polysaccharides: cellulose and chitin. Storage polysaccharides: starch and glycogen. Carbohydrates as renewable raw material for fine chemicals. (1.5 CFU)
Nucleic acids. Structure, properties and nomenclature. Nucleosides and nucleotides. Purine and pyrimidine heterocycles. DNA bases. Acid-base characteristics, tautomeric forms, and reactivity. Nucleosides: structure and biological properties. Phosphate, pyrophosphate and triphosphate esters. Nucleotides. Nucleic acids. Polynucleotide structure. Chemical stability and main reactions of DNA and RNA: hydrolysis, oxidation and alkylation. Chemical sequencing of DNA and its scope of use. Chemical synthesis of DNA and DNA, protecting groups. (0.5 CFU)
Lipids. Structure and properties. Lipid classification. Auto-oxidation and photo-oxidation reactions. Synthesis of complex lipids: some examples. Phospholipids and glycolipids. Micelles and liposomes. Main classes of non-saponifiable lipids. (1 CFU)
Lessons: Green chemical technologies for sustainable recovery and transformation of bioactives from agri-food waste and residues (1.5 CFU)
Lessons: Main spectroscopic techniques for chemical structural analysis. The mechanism of interaction between radiation and matter. The electromagnetic spectrum. Fundamental and excited states. Absorption and emission spectroscopies. Ultraviolet-Visible (UV-VIS) Spectroscopy and Chiroptical methods Electronic transitions and UV-vis absorbance. Electronic, vibrational and rotational energy levels. Molecular orbitals and electronic transitions in isolated and conjugated alkenes, in carbonyl compounds, in benzene and heteroaromatic compounds. Spectral features of purines, pyrimidines, aromatic aminoacids. (0.5 CFU)
Lessons: Nuclear Magnetic Resonance (NMR). Magnetic properties of the atomic nucleus. Energy and frequency of nuclear spin transitions. Pulsed NMR and Fourier Transform NMR. The chemical shift. Structural factors influencing the chemical shift. Signal multiplicity. Geminal and vicinal couplings. "long range" couplings. Chemical and magnetic equivalence. Examples of analysis of the main spin-systems. The Nuclear Overhauser Effect for the determination of proton-proton distances. Heteronuclear spectroscopy: 13C-NMR. 31P-NMR, 15N-NMR. Coupled and decoupled spectra. Application examples in the biotechnology and food industry. Introduction to 2D-NMR spectroscopy. (0,5 CFU)
Class tutorials. Structure determination of unknown compounds by joint analysis of UV and 1H/13C-NMR spectra. Class tutorials. (0.5 CFU)
Lab. Tutorials. Biodiesel preparation through biocatalytic approaches and product characterization by spectroscopic and chromatography techniques (TLC, UV, NMR); application of UV methodologies for the determination of the enzymatic specific activity. (0.5 CFU)
Carbohydrates. Structure, properties, nomenclature. Anomeric effect. Oxidation and reduction reactions. Glycosylation reactions: concept of glycosyl donor and glycosyl acceptor, promoters, protecting groups. Chemo-enzymatic synthesis of glycosidic bond. Oligosaccharide and glycoconjugates synthesis on solid phase. Structural polysaccharides: cellulose and chitin. Storage polysaccharides: starch and glycogen. Carbohydrates as renewable raw material for fine chemicals. (1.5 CFU)
Nucleic acids. Structure, properties and nomenclature. Nucleosides and nucleotides. Purine and pyrimidine heterocycles. DNA bases. Acid-base characteristics, tautomeric forms, and reactivity. Nucleosides: structure and biological properties. Phosphate, pyrophosphate and triphosphate esters. Nucleotides. Nucleic acids. Polynucleotide structure. Chemical stability and main reactions of DNA and RNA: hydrolysis, oxidation and alkylation. Chemical sequencing of DNA and its scope of use. Chemical synthesis of DNA and DNA, protecting groups. (0.5 CFU)
Lipids. Structure and properties. Lipid classification. Auto-oxidation and photo-oxidation reactions. Synthesis of complex lipids: some examples. Phospholipids and glycolipids. Micelles and liposomes. Main classes of non-saponifiable lipids. (1 CFU)
Lessons: Green chemical technologies for sustainable recovery and transformation of bioactives from agri-food waste and residues (1.5 CFU)
Lessons: Main spectroscopic techniques for chemical structural analysis. The mechanism of interaction between radiation and matter. The electromagnetic spectrum. Fundamental and excited states. Absorption and emission spectroscopies. Ultraviolet-Visible (UV-VIS) Spectroscopy and Chiroptical methods Electronic transitions and UV-vis absorbance. Electronic, vibrational and rotational energy levels. Molecular orbitals and electronic transitions in isolated and conjugated alkenes, in carbonyl compounds, in benzene and heteroaromatic compounds. Spectral features of purines, pyrimidines, aromatic aminoacids. (0.5 CFU)
Lessons: Nuclear Magnetic Resonance (NMR). Magnetic properties of the atomic nucleus. Energy and frequency of nuclear spin transitions. Pulsed NMR and Fourier Transform NMR. The chemical shift. Structural factors influencing the chemical shift. Signal multiplicity. Geminal and vicinal couplings. "long range" couplings. Chemical and magnetic equivalence. Examples of analysis of the main spin-systems. The Nuclear Overhauser Effect for the determination of proton-proton distances. Heteronuclear spectroscopy: 13C-NMR. 31P-NMR, 15N-NMR. Coupled and decoupled spectra. Application examples in the biotechnology and food industry. Introduction to 2D-NMR spectroscopy. (0,5 CFU)
Class tutorials. Structure determination of unknown compounds by joint analysis of UV and 1H/13C-NMR spectra. Class tutorials. (0.5 CFU)
Lab. Tutorials. Biodiesel preparation through biocatalytic approaches and product characterization by spectroscopic and chromatography techniques (TLC, UV, NMR); application of UV methodologies for the determination of the enzymatic specific activity. (0.5 CFU)
Prerequisites for admission
Basic knowledge of the structure and nomenclature of the main functional groups in organic chemistry. Basic knowledge of biochemistry. For any question and further details please contact the teacher at [email protected] or [email protected].
For both attending and non-attending Students.
For both attending and non-attending Students.
Teaching methods
Lessons: 7CFU
Class tutorials: 0.5CFU
Laboratory tutorials: 0.5CFU
Class tutorials: 0.5CFU
Laboratory tutorials: 0.5CFU
Teaching Resources
a) E. Rossi, D. Nava, G. Abbiati, G. Celentano, S. Pandini "Structure determination of organic compounds, practical exercise" Ed. EdiSES; b) Biochemistry- 4th Edition Voet & Voet Wiley; c) Organic Chemistry - 4th Edition - Clayden, Greeves, Warren and Wothers-Oxford University Press, Wiley and Sons; d) Slides of lessons available through the Ariel Web Site
For both attending and non-attending Students.
For both attending and non-attending Students.
Assessment methods and Criteria
The examination is in the written form. Four questions will be asked: a) the student should be able to describe the structure of a simple organic molecule on the basis of the provided spectroscopic data; b) a theoretical question about general aspects of molecular spectroscopy; c and d) two questions related to synthetic aspects and the description of structure-activity relationships of specific classes of compounds described in the course. Students should answer to all questions within 2 hours. To each question a formal maximum value of 8 points will be assigned.
Examinations will be evaluated according to the following criteria:
1. Proof of understanding of the topics covered during lectures and laboratory practices.
2. Ability to answer, in a critical and integrated way, using the correct terminology and chemical drawings.
3. Completeness of the answers.
Laboratory reports will be considered as well for the final evaluation. At least 7 exam sessions per year will be guaranteed. The date of the exam will be published on SIFA platform.
Specific procedures for exams to students with disabilities or specific learning disabilities (DSA) will be applied. Here the complete information:
https://www.unimi.it/en/study/student-services/services-students-specific-learning-disabilities-sld
https://www.unimi.it/en/study/student-services/services-students-disabilities
In case you need specific procedures, please inform the teacher by mail at least 10 days before the exam, including in the addresses [email protected] or [email protected]
For both attending and non-attending Students.
Examinations will be evaluated according to the following criteria:
1. Proof of understanding of the topics covered during lectures and laboratory practices.
2. Ability to answer, in a critical and integrated way, using the correct terminology and chemical drawings.
3. Completeness of the answers.
Laboratory reports will be considered as well for the final evaluation. At least 7 exam sessions per year will be guaranteed. The date of the exam will be published on SIFA platform.
Specific procedures for exams to students with disabilities or specific learning disabilities (DSA) will be applied. Here the complete information:
https://www.unimi.it/en/study/student-services/services-students-specific-learning-disabilities-sld
https://www.unimi.it/en/study/student-services/services-students-disabilities
In case you need specific procedures, please inform the teacher by mail at least 10 days before the exam, including in the addresses [email protected] or [email protected]
For both attending and non-attending Students.
CHIM/10 - FOOD CHEMISTRY - University credits: 8
Practicals: 8 hours
Laboratories: 8 hours
Lessons: 56 hours
Laboratories: 8 hours
Lessons: 56 hours
Professors:
Contente Martina Letizia, Pinto Andrea
Shifts:
Educational website(s)
Professor(s)