Solid phase peptide synthesis using 2-(4-Nitrophenyl)-sulfonylethoxycarbonyl (NSC) amino acids for Luteinizing hormone-releasing hormone (LHRH)

Abstract

The Nα-9-fluorenylmethoxycarbonyl (Fmoc) amino acid groups are base labile. This characteristics have been widely applied to the solid phase peptide synthesis to replace acid-labile t-butoxycarbonyl(BOC) amino protecting groups. However, the extreme base sensitivity of Nα-Fmoc-protected group unstable in neutral aprotic solvents is one of the disadvantages of Fmoc-amino acids. 2-(4-Nitrophenyl) sulfonylethoxycarbonyl (Nsc) group can be used as the appropriate protecting group for Na-amino acids in SPPS application and liquid phase peptide synthesis [1]. Base-labile Nscand Fmoc-protecting groups are compared as temporary Nα-amino protection in the automated SPPS of Luteinizing hormone-releasing hormone (LHRH) and (D -Trp6 )– LHRH on MilliGen 9050+ PepSynthesizer