Highly Efficient Synthetic Method on Pyroacm Resin Using the Boc SPPS Protocol for C‐terminal Cysteine Peptide Synthesis

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...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2017, 38(1), , pp.54-62
Main Authors: Juvekar, Vinayak, Kim, Kang‐Tae, Gong, Young‐Dae
Format: Article
Language:English
Subjects:
C‐terminal cysteine
Side chain anchoring
Solid‐phase peptide synthesis
Thiol‐sulfenyl protection
β‐Elimination
화학
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Summary: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.
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.11045