Alkylation of Peptide Bonds to Decrease Aggregation 2-Hydroxybenzyl Protectors

5 ALKYLATION OF PEPTIDE BONDS TO DECREASE AGGREGATION 2-HYDROXYBENZYL PROTECTORS 

FIGURE 8.7 Synthesis of a protected tripeptide containing a 2-hydroxy-4-methoxybenzyl-protected peptide bond.38 (A) Acylation of the carboxy-terminal residue, (B) removal of both protecting groups, (C) O-acylation of the benzyl-protector by the symmetrical anhydride of the amino-terminal residue, and (D) migration of the protected amino-terminal residue from the oxygen atom to the amino group of the dipeptide ester. 

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