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Synthesis of protected norcysteines for SPPS compatible with Fmoc-strategy
Manoj P Samant1, Jean E Rivier
1The Clayton Foundation Laboratories for Peptide Biology, The Salk Institute, La Jolla, California 92037, USA.
Abstract:
We report the synthesis of racemic Alloc-Ncy(Tmob)-OH, the resolution of its methyl ester, and demonstrate its application to form a norcystine bridge in octreotide-amide using the Fmoc-strategy on solid phase. N-Alloc and S-Tmob protections of norcysteine (Ncy) were found to be a preferred choice for Fmoc-strategy over three other protected norcysteines synthesized i.e. Fmoc-Ncy(tBu)-OH, Alloc-Ncy(tBu)-OH and Alloc-Ncy(Trt)-OH.
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