Synthesis of peptides containing three disulfide bonds: can it be fully automated?

I have experimented a lot with disulfide rich peptides lately, finding conditions that work well for not only the linear synthesis, but also for on-resin cysteine oxidations.  Although simple scaffolds are useful for determining orthogonal protecting group removal and cysteine oxidation conditions, many of the peptides of interest today are much more complex – three or more disulfide bonds, and often head-to-tail cyclization.

In today’s post, I put to use three orthogonal protection strategies to optimize a fully automated synthesis of linaclotide.

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