Stereochemistry and chirality. Amino acids and peptides. Peptides having biological activity. Chemical synthesis of peptides: protecting groups, activating groups, in solution and in heterogeneous phase. Combinatorial chemistry applied to libraries of peptides. Analysis of the peptides and methods of biological screening. Bioconjugation techniques which allow the monitoring and the study of biomolecules through the formation of covalent bonds with molecules of easy detection and radionuclides.
V.Santagada and G.Caliendo, Peptidi e peptidemimetici. 2003 Piccin Nuova Libraria – Padova
Greg T. Hermanson, Bioconjugate Techniques. Academic Press USA
Introduction to Stereochemistry and Conformational Analysis. Eusebio Juaristi. ISBN: 978-0-471-54411-1. 352 pages. October 1991 Wiley
Materials provided by the teacher.
Learning Objectives
The aim of the course is to provide detailed knowledge of the properties of the main classes of biomolecules and their chemical behavior.
The student will be able to design a peptide synthesis and libraries of compounds with potential biological activity. In addition the student will recognize in the main biomolecules (peptides and proteins, sugars and polysaccharides, nucleic acids and oligonucleotides) the functional groups suitable for labeling with fluorophores or radionuclide and employable synthesis strategies to express on them functional groups not normally present. Know the main classes of fluorophores and their capabilities for bioconjugation.
Prerequisites
Courses recommended: General and Inorganic Chemistry, Organic Chemistry.
Teaching Methods
Total hours of the course: 150.
Hours reserved to private study and other individual formative activities: 102
Contact hours for Lectures: 48 hours including 8 hours for laboratory exercises.
Further information
Frequency of lectures and exercises: Highly recommended
Teaching tools: Power point presentations of the lectures, Moodle program.
Type of Assessment
The examination includes an oral text to ascertain the understanding and ability to explain in a clear and appropriate way the topics of the course. It will also be evaluated for their ability to apply their knowledge to some practical problems (synthesis design of biologically active molecules or traformation of functional groups present on biomolecules for labeling with the appropriate agents).
Course program
Fundamentals of stereochemistry, centers, axes and chiral planes, enantiomers and stereoisomers. Methods of obtaining enantiomers. Methods of characterization of enantiomers.
Peptides. Nomenclature. Cis-trans isomers of the peptide bond. Acidity in peptides, calculation of the isoelectric point. Hydrolysis in an acidic and in a basic environment. Examples of peptides having biological activity.
Chemical synthesis of peptides: protecting groups and activating groups, in solution methods and methods in solid phase, Boc and Fmoc strategies. Conjugated peptides, cyclic peptides, peptide-mimetics. Combinatorial chemistry applied to libraries of peptides. Analysis of the peptides.
Preparation of libraries of organic compounds and biological screening methods.
Bioconjugation techniques which allow the monitoring and the study of biomolecules through the formation of covalent bonds with molecules of easy detection and radionuclides; using special synthetic strategies the individual properties of the two components are combined and maintained unchanged. The bioconjugation techniques are used in all disciplines of the life sciences, allowing the dosage of micro quantities of materials, the in vivo labeling of molecules, modulation of specific biological processes, treatment of diseases, the study of the structure and function of the proteins, as well as the conformation of their active sites, and finally the purification, determination and localization of specific cellular components.
Analysis of the functional groups available for the bioconjugation and synthesis strategies employable to express from these functional groups not normally present in biomolecules of main interest, peptides and proteins, sugars and polysaccharides, nucleic acids and oligonucleotides. Survey of the functional groups that the easy molecule detectability should possess and of the functional groups that are formed as a result of bioconjugation. The properties used for detection will then be evaluated: absorption, radioactivity, fluorescence, biotin markers, followed by examining the main molecules capable of expressing these properties even in the light of their availability on the market. Particular emphasis will be finally given to modern fluorescence fluorophores that are one of the main properties used in bioconjugation: fluoresceine, rodamine, cyanine, coumarin.