Chemistry 30A3 Fall 2011 Labs Dr. Troendle 40

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 40 - the polymer...

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Chemical Biology 3OA3, September 2009 Page 40 Many advances on the original Merrifield procedure have been developed. In this experiment, you will use the Rink Tentagel amide resin to synthesize your peptide amide. This methodology uses fluorenylmethoxycarbonyl (Fmoc) groups to protect the amino groups of each amino acid, rather than the tBoc group used by Merrifield; these Fmoc groups are more quickly and efficiently removed when needed, using piperidine in DMF. The Rink resin arrives with an Fmoc group attached, so this reaction is the first chemistry you’ll perform on your resin, after washing and swelling. Removal of the Fmoc group on the resin yields a free amine attached to
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Unformatted text preview: the polymer support, and you are ready to attach the first amino acid. N H O O NH OMe OMe O O H N H N H O O NH 2 OMe OMe N H O O NH OMe OMe O R1 NHFmoc R1 O O H NHFmoc N N N O N+Me 2 Me 2 N N N N R1 O O NHFmoc PF 6-N H O O NH OMe OMe O R1 N H O R2 N H O R3 etc. ...NH 2 N H O O OMe OMe OH CF 3 CO 2 H NH 2 O R1 N H O R2 N H O R3 etc. ...NH 2 N Resin Bead (Polystyrene) Rink Resin as Supplied Piperidine, DMF } Fmoc group + Amino acid #1 HBTU (1) Piperidine, DMF (2) Amino acid #2 plus HBTU, etc. (3) Piperidine, DMF Peptide Amide Spent Resin + mix mix (TFA) + DIPEA (a base)...
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