ASUC chem 29

ASUC chem 29 - CHEMISTRY 3B Professor Peter Vollhardt...

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CHEMISTRY 3B Professor Peter Vollhardt 12/09/08 Lecture 29 ASUC Lecture Notes Online is the only authorized note-taking service at UC Berkeley. Do not share, copy or illegally distribute (electronically or otherwise) these notes. Our student-run program depends on your individual subscription for its continued existence. These notes are copyrighted by the University of California and are for your personal use only. D O N O T C O P Y Sharing or copying these notes is illegal and could end note taking for this course. LECTURE Synthesis of polypeptides We need protecting groups because of selectivity in building up the peptide sequence. a. Amino end protection with Cbz b. Amino end protection with Boc c. Carboxy end protection with esterification Simple methyl or ethyl esters. Alternatively, to avoid base (or acid) hydrolysis, benzyl esters. Formation of the amide bond for dipeptides uses a mild coupling reagent: DCC as a dehydrating species Mechanism: 1. Activation of carboxy group of N-protected amino acid 2. Coupling with amino end of carboxy end protected amino acid to give dipeptide
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ASUC chem 29 - CHEMISTRY 3B Professor Peter Vollhardt...

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