Abstract
Automated and manual deprotection methods for allyl/allyloxycarbonyl (Allyl/Alloc) were evaluated for the preparation of side-chain-to-side-chain cyclic peptides. Using a standard Allyl/Alloc deprotection method, a small library of cyclic peptides with lactam bridges (with seven amino acids) was prepared on an automatic peptide synthesizer. We demonstrate that the Guibé method for removing Allyl/Alloc protecting groups under specific neutral conditions [Pd(PPh3)4/PhSiH3)/DCM] can be a useful, efficient and reliable method for preparing long cyclic peptides on a resin. We have also manually synthesized a cyclic glucagon analogue containing 24 amino acid residues. These results demonstrated that properly controlled palladium-mediated deprotection of Allyl/Alloc protecting groups can be used to prepare cyclic peptides on the resin using an automated peptide synthesizer and cyclic peptides with a long chain.
Original language | English (US) |
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Pages (from-to) | 250-256 |
Number of pages | 7 |
Journal | Journal of Peptide Research |
Volume | 57 |
Issue number | 3 |
DOIs | |
State | Published - 2001 |
Externally published | Yes |
Keywords
- Allyl/Alloc strategy
- Automated synthesis
- Cyclic peptides
- Side-chain-to-side-chain cyclization
- Solid-phase synthesis
ASJC Scopus subject areas
- Biochemistry
- Endocrinology