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Lecture 39

CHE 322 Lecture 39: Ch 25: thioesters, organophosphates
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Department
Chemistry
Course
CHE 322
Professor
Dale Drukheimmer
Semester
Spring

Description
Lecture 38 Throeste ond Organophosphates LAI H 412% /20 (1 OH SEt HMG-CoA H.2NADP CH-CH S-coA 2, 2H30+ NADPH COA SH OHA NADH and NADPH ore hydri e sources in biochemistry Thio esters react similarly to esters Soponification reachvity similar to esters HSCH2CH C C pKa th spra alcohol) Thiol Sh be better lea g group a hon thio Stab ers is weaker than that of esters einahe dra ediate is better stab a by more electro ative LO than by less ele Honeg ative. pKa & resonance stabilizarion are evened out by stabilization Antermo diate. Acid catalyzed hydrolysis strong acid re Thio ester oxygen is less nucleophilic than ester oxygen- Transesterification tert thiol th10 thioester t alcohol Acetylc holin terase & Nerve Agents (muscle is releas n to synapses to trigger a response nt action alter release It mu bo broken down apidly by enzt AChE to prevent co ued response Phosphoric acid Derivatives dimethyl phosphate methyl phosphate acid o CH30 OCH3 OH CH30 0H 2.3 tt 1.4 phosphates can be H20 CH30 OCH rauw er encu Vale CH30 S possible CH30 30 S KJ/mol ATP- CAG Base -promoted Ccompare to car boxylate ester hyarolysis) Addition Eliminated Mechanism 10 Lecture 38 Throeste ond Organophosphates LAI H 412% /20 (1 OH SEt HMG-CoA H.2NADP CH-CH
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