Tetrahydropyranyl Backbone Protection for Enhanced Fmoc Solid-Phase Peptide Synthesis.

ABSTRACT: Fmoc solid-phase peptide synthesis has been indispensable for the efficient manufacture of research grade peptides and proteins, and peptide APIs. However, the solid-phase approach is still hampered by solubility issues and aggregation of the resin-bound peptide chain, which limits routine access to peptides > 40 amino acids in length. The use of backbone amide protecting groups, such as through the introduction of N-benzyl-based moieties and pseudoproline dipeptides, ameliorates this synthetic inefficiency somewhat. But benzyl groups can be difficult to remove postassembly, and pseudoprolines are limited to serine, threonine, and cysteine-rich peptide segments. To enhance the utility of backbone protection, we have evaluated the tetrahydropyranyl (Thp) group as a more acid labile alternat

SUBMITTER: Paravizzini SJ 

PROVIDER: S-EPMC12351424 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature