CHEM 313 Chapter Notes -Oxazolone, Triethylamine, Bioorganic Chemistry

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Assuming a modest peptide has 50 amino acids, there will be 32x50 potential conformations of the polymer chain, i. e. , over 5 x 1047 conformations. However, in reality there are limits to the number of conformations observed. For a defined peptidic sequence there is a small set of conformations in which the ground level energy (most stable) has been minimized. Among different molecular forces, one is particularly important to stabilize in a directional fashion a particular set of conformations (most stable). The co2(g) gassing out drives the reaction to completion. Not only is it a good base, it also quenches the byproduct of the reaction. What problems affecting the peptide could occur when triethylamine is used in its place? (tertiary amines are slow in deprotection of fmoc-amino acids but if enough time is given, it will happen. However, sterically hindered tertiary amine, such triethylamine, is a poor nucleophile)