Premium
Highly Efficient Synthetic Method on Pyroacm Resin Using the Boc SPPS Protocol for C‐terminal Cysteine Peptide Synthesis
Author(s) -
Juvekar Vinayak,
Kim KangTae,
Gong YoungDae
Publication year - 2017
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11045
Subject(s) - cysteine , peptide , cleavage (geology) , chemistry , peptide synthesis , combinatorial chemistry , native chemical ligation , side chain , solid phase synthesis , organic chemistry , biochemistry , materials science , enzyme , fracture (geology) , composite material , polymer
A very effective process on Pyroacm resin was developed for solid‐phase peptide synthesis ( SPPS ) of C‐terminal cysteine and cysteine ester peptides. The process uses cysteine side chain anchoring to the Pyroacm resin and the Boc protocol for SPPS . The Pyroacm resin showed remarkable stability under standard trifluoromethanesulfonic acid ( TFMSA ) cleavage condition. TFMSA cleavage of protecting groups generates a peptide‐linked resin, which can be subjected to peptide modification reactions. Finally, the peptide can be cleaved from the resin using methoxycarbonylsulfenyl chloride. The utility of this protocol was demonstrated by its applications to the synthesis of model peptides, key intermediates in the preparation of natural products riparin 1.2 and a‐factor.