Aminolysis of Succinimido Esters by Unprotected Amino Acids or Peptides

21 AMINOLYSIS OF SUCCINIMIDO ESTERS BY UNPROTECTED AMINO ACIDS OR PEPTIDES 

FIGURE 7.31 Aminolysis of a succinimido ester by (A) an amino-acid anion generated by base [Anderson et al., 1974] and (B) a peptide anion that is in equilibrium with the peptide.114 Pg = protecting group. Appropriate solvents are tetrahydrofuran, acetone, or dimethylforma-mide with water. 

JW Anderson, JE Zimmerman, FM Callahan. The use of esters of A-hydroxy suc-cinimide in peptide synthesis. J Am Chem Soc 86, 1839, 1964. 

L Moroder, W Gohring, P Lucietto, J Musiol, R Schaarf, P Thamm, G Bovermann, G Wiinsch, J Lundberg, G Tatemoto. Synthesis of porcine intestinal peptide PHI and its 24-glutamine analog, (aminolysis without base). Hoppe Seyler s Z Physiol Chem 364, 1563, 1983. 

NL Benoiton, YC Lee, FMF Chen. Racemization during aminolysis of activated esters of A-alkoxycarbonylamino acids by amino acid anions in partially aqueous solvents and a tactic to minimize it. Int J Pept Prot Res 41, 512, 1993. 

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