Ch_322b_24.09

Ch_322b_24.09 - Synthesis of Polypeptides Simple...

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Synthesis of Polypeptides Simple Polypeptide Synthesis Small polypeptides may be synthesized by properly introducing protecting and activating groups before the coupling step. example: Ala.Leu H 3 NCHCO 2 - CH 3 + Ala H 3 NCHCO 2 - + CH 2 CH(CH 3 ) 2 Leu protection of N-terminal group in Ala H 3 NCHCO 2 - CH 3 + + C 6 H 5 CH 2 OCCl O = benzyl chloroformate HO - 25 o C C 6 H 5 CH 2 OC NHCHCOOH O CH 3 N-benzyloxylcarbonyl activation of carbonyl C 6 H 5 CH 2 OC NHCHCOOH O CH 3 (i) Et 3 N: (ii) ClCOC 2 H 5 O Q Q NHCHC OCOC 2 H 5 CH 3 O O active leaving group
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coupling Q NHCHC OCOC 2 H 5 CH 3 O = O H 3 NCHCO 2 - + CH 2 CH(CH 3 ) 2 Leu + N-protected and activated Ala Q NHCHCNHCHCOOH CH 3 O CH 2 CH(CH 3 ) 2 Q-Ala.Leu deprotection C 6 H 5 CH 2 OC NHCHCNHCHCOOH O CH 3 O CH 2 CH(CH 3 ) 2 H 2 /Pd H 3 NCHCNHCHCO 2 - CH 3 + O CH 2 CH(CH 3 ) 2 Ala.Leu + C 6 H 5 CH 3 + CO 2
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Automated Peptide Synthesis: The Merrifield Method In the 1960s, R. Bruce Merrifield developed an automated peptide synthesis method at Rockefeller University. This computer-controlled process allows polypeptides with a hundred or more amino acid residues to be synthesized by a machine. Commercial instruments quickly became available that revolutionized peptide synthesis. Merrifield received the Nobel Prize in Chemistry in 1984 for his
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This note was uploaded on 01/23/2011 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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Ch_322b_24.09 - Synthesis of Polypeptides Simple...

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