Bioorganic Chemistry: A Chemical Approach to Enzyme Action by Hermann Dugas

By Hermann Dugas

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II S-C-CH /NH2 "CH-CH 3 I CH 3 .......... - heavy;::::' enz. 5 Biological Synthesis of Proteins The next step involves an "arm" on the heavy enzyme. This arm "picks up" or attacks the tripeptide via its thiol function. It is then attacked by ornithine to form a tetrapeptide, but picks up the tetrapeptide (via the same thiol) and is attacked by leucine to form a penta peptide. The arm again retrieves the pentapeptide, but this time the penta peptide is attacked by a complementary pentapeptide (attached to another arm) to give rise to the cyclic decapeptide.

This dipeptide could then be treated with phenylisothiocyanate so that the second amino acid residue could be identified as its thiohydantoin derivative. 4 Acylations S II~. ( HN Y NH "Ph S 0 t1 HN N- Y S Ph + starting from the N-terminus. This procedure is referred to as the Edman degradation. Other acylation reactions are of importance for the protection of the amino function during protein synthesis. These shall be discussed shortly. The amide bond resulting from the acylation of amino acids is a planar hybrid structure, with an approximately equal distribution between two resonance forms.

1) and amino acids are not peculiar in this regard. For example, halogenation of acetic acid produces an even stronger acid so that acid strength increases in the order acetic acid < monochloro- < dichloro- < trichloroacetic acid. This reflects the inductive (Ie) pull, or withdrawal of electron density from the carboxyl, by the electronegative chlorine atoms through the covalent linkages of the acid molecule. A perturbation or change in electron density through the (J bonds may be imagined. 2 Dissociation Behavior Hence, replacement of three chlorine atoms with three more electronegative fluorine atoms results in an even stronger acid: trifluoroacetic acid.

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