Solid phase synthesis and combinatorial technologies

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With the oral examination it will be possible to assess the competence of the students on the general principles of combinatorial chemistry and on the specific subject of solid-phase synthesis. Skip to main content. Study with us. Incoming students Courses Units Ph. Meteorological alert status. Teaching materials. OVERVIEW The course is aimed at giving basic knowledge about modern techniques and approaches to prepare large collections of compounds for applications in medicine, catalysis and material science.

These approaches can be all included in the term "Combinatorial chemistry" As combinatorial chemistry was introduced as a synthetic strategy in the drug discovery process, the first part of the course will mainly focus on organic chemistry aspects. AIMS AND LEARNING OUTCOMES The student at the end of the course will be able to: -use search engines to find -in the relevant literature- combinatorial applications in all fields of material science -collect articles and critically analyze them, for what concerns the combinatorial approaches which have been used -design a simple combinatorial experiment to prepare libraries of materials -individuate general analytical techniques needed to carachterize the libraries.

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Teaching methods Lectures, bibliographic search through serching engines, powerpoint presentations. Andrea Basso. Assessment methods The students will be asked to prepare a powerpoint presentation on a specific subject, chosen in agreement with the teacher. The student will present the work in front of the classroom and the evaluation will be mainly on four aspects 1. Equations displayed with MathJax. Right click equation to reveal menu options.

Solid phase peptide synthesis

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The combinatorial modification of yohimbinic acid, a natural alkaloid, was reported by Atuegbu et al. R 2 : from 22 carboxylic acids. The biological evaluation of the library was not reported. The commercially available natural scaffold is known to possess a wide range of biological activities, and the possibility to further expand the two monomer sets make such a primary library a likely source for new biologically active analogues.

There is a real possibility of building a preliminary structure activity relationship SAR and of finding substituents that favor different biological activities providing that the decoration of the natural product diversifies the library components enough. Another decoration pool library L23 was reported by Nestler 49 , who presented the appendage of a peptidic chain to the two hydroxylic functions of a steroid scaffold Fig.

The assay of the library as a source of artificial two-armed receptors for enkephalin-related peptides produced positives with micromolar affinity. Much larger libraries could be obtained by simply increasing the monomer sets and the length of the two arms; this could lead to a primary library of peptide-binding artificial receptors; similar scaffolds have been repeatedly exploited for combinatorial purposes 50— The natural scaffold, or a scaffold resembling a natural product, can also be built during the synthesis of the library.

An example presented by Nielsen and Lyngsoe 55 involved the synthesis of a library L26 inspired by the structure of balanol Fig. Introduction of modified building blocks aliphatic diacids or monoacids, acyclic or aromatic amino alcohols, etc. A more complex combinatorial strategy based on a natural scaffold was reported by Nicolaou et al.

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The library was prepared using a radiofrequency encoding technique 42 , and the final. R 1 : 3 primary amines n -propyl, benzyl and cyclohexyl. R 2 : 5 carboxylic acids acetic, benzoic, 4-pyridyl, phenylacetic and acrylic. R 3 : 2 carboxylic acids acetic and benzoic.

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The monomer sets consisted of three protected hydroxy aldehydes R 1 , three protected hydroxy keto acids R 2 , and five heterocyclic secondary alcohols R 3 prepared using published multistep routes, and the expansion of these sets would require significant synthetic effort. Once such an ambitious synthetic scheme has been set up, it would be desirable to move away from the initially used biased monomer sets and to introduce more diverse commercially available monomers to build larger, less epothilone-like libraries with the same synthetic strategy that could be used as primary libraries to search for other biological activities.

This example shows that even complex natural scaffolds can be dissected and reconstructed using appropriate reactions and monomer sets. Biological libraries can also be produced by combinatorial.

Solid–Phase Synthesis and Combinatorial Technologies

Some biological libraries are reported in Figs. An application of phage display libraries to the identification of peptidic sequences that selectively target tumor blood vessels was reported by Arap et al. Three cyclic peptide libraries were produced by inserting the corresponding degenerate oligonucleotide sequences into a vector fUSE 5 , then transforming MC cells by. All three of them delivered peptidic sequences preferentially to the tumor and seemed to bind to different tumor receptors. Their use as drug delivery systems for the development of targeted chemotherapy looks extremely promising.