Acceleration of the N alpha-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1.
In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile alpha-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N alpha-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and NG-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.
Tamamura
H
H
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Nakamura
J
J
Noguchi
K
K
Funakoshi
S
S
Fujii
N
N
D000595:Amino Acid Sequence; D023181:Antimicrobial Cationic Peptides; D003408:Cresols / Q000737:chemistry*; D006801:Humans; D008698:Mesylates / Q000737:chemistry*; D008969:Molecular Sequence Data; D010187:Pancreatic Hormones / Q000138:chemical synthesis*; D010446:Peptide Fragments / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*; D029867:Xenopus Proteins
D023181:Antimicrobial Cationic Peptides; D003408:Cresols; D008698:Mesylates; D010187:Pancreatic Hormones; D010446:Peptide Fragments; D010455:Peptides; D029867:Xenopus Proteins; C053300:magainin 1 peptide, Xenopus; C071103:pancreastatin-29; C045880:methanesulfonic acid; C042041:3-cresol