215F07-notes-12-3-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 3. Date: December 3, 2007 (5) Solid-Phase Peptide Synthesis (Chapter 21.8, pp 900-906) Developed by Robert Merrifield in 1969; has been automated. A large number of polypeptides have been prepared by the use of automated peptide synthesizers. The most significant difference between solution-phase and solid-phase peptide synthesis lies in the fact that the solid-phase synthesis of peptides is carried out in the opposite direction, starting with the C -terminus attached to the solid support and proceed toward the N -terminus, i.e., from right to left as the peptide chain is drawn. Synthesis of Val-Ala-Gly as an example : After each reaction step, the product attached to the polymer bead is collected by filtration and all reagents, etc. dissolved in the solvent are thus removed. The product attached to the bead is then exposed to the new reagents dissolved in the solvent for the next reaction step. styrene polystyrene (polymer; solid support) polymerization H 2 C H 2 C Cl Cl ClCH 2 OCH 3 SnCl 4 CHCl 3 (solvent) Comments : 1. Heterogenous reaction 2. Friedel-Crafts alkylation involving +CH 2 OCH 3 (or CH 2 =O + -CH 3 ).
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