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Extra info for Bioorganic Chemistry: A Chemical Approach to Enzyme Action

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Furthermore, the thiol is a much better leaving group than the corresponding alcohol. 1). * For the most recent chemical synthesis of gramicidin S, see reference 364. :::;- 6 / :"J- ~ light~ " CH2 Ad~j 0 : I 0II (B NH3 S-C-CH / 0 "C enz. ;:: -AMP f ~ HO OH In the next step, proline attached to the heavy enzyme by a thiol ester linkage attacks the light enzyme, thus transferring the dipeptide to the heavy enzyme. The function of the light enzyme is terminated. ~ ~ :~:~y@ q H:\ 13 ~--O N S-C . S V ~.

First, specificity or sequential coupling of the amino acids must be achieved. Unwanted side reactions must be avoided. Consider, for example, the synthesis of the dipeptide glycylalanine (Gly-Ala). It is not possible to mix the two amino acids together and let them react as the desired sequence will not be the only product. 6 Chemical Synthesis of Proteins 55 react with itself to give the dipeptide glycylglycine. In fact, the number of possible dipeptides is four (Gly-Gly, Gly-Ala, Ala-Gly, Ala-Ala), of which only one is the correct sequence.

Puromycin will act equally well on protein synthesis in mammalian cells and so is not a practical antibacterial agent. On the other hand, the antibiotic chloramphenicol binds to the bacterial ribosomes, but not the larger ribosomes of animals, thereby showing greater specificity. This inhibits peptide bond formation. Chloramphenicol is relatively nontoxic, but it still must be used with caution as side effects such as anemia can result. Other antibiotics which inhibit protein synthesis include the tetracyclines, streptomycin, and cycloheximide.

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