8B-handout-feb20-aspirin

8B-handout-feb20-aspirin - Chem 8B, Handout for Feb 18,...

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Chem 8B, Handout for Feb 18, 2009, Aspirin: Mechanism of Pain Relief Sections 12.3-12.13, 19.2 and 13.4 Recall, the synthesis of aspirin is the acetylation of salicyclic acid: OH OH O O OH O H 3 C O CH 3 O O O H 3 C salicylic acid acetylsalicylic acid aspirin TM acetylation reaction O CH 3 O H + acetic acid acetic anhydride alcohol nucleophiile carbonyl electrophile substitution product is an ester acetic acid (vinegar) is the by-product (conjugate acid of the leaving group) Well… it turns out that the way our body reacts with aspirin to relieve pain is the reverse reaction that is used to synthesize the aspirin (see below and on page 306 in your Bruice Textbook for more information). A nucleophilic oxygen attacks the ester of the aspirin to transfer the acetyl group to a COX enzyme (a covalent, irreversible inhibition of the enzyme), and gives back the salicylic acid (see below). Specifically, a serine amino acid residue (Ser) is an example of a biological alcohol (an oxygen nucleophile) that can react with the ester electrophile on the aspirin molecule. However,
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This note was uploaded on 03/12/2009 for the course CHE 8B taught by Professor Lievens during the Winter '07 term at UC Davis.

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8B-handout-feb20-aspirin - Chem 8B, Handout for Feb 18,...

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