Preparation of ‘side‐chain‐to‐side‐chain’ cyclic peptides by Allyl and Alloc strategy: potential for library synthesis
- 1 March 2001
- journal article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 57 (3) , 250-256
- https://doi.org/10.1111/j.1399-3011.2001.00816.x
Abstract
Automated and manual deprotection methods for allyl/allyloxycarbonyl (Allyl/Alloc) were evaluated for the prepn. of side-chain-to-side-chain cyclic peptides. Using a std. Allyl/Alloc deprotection method, a small library of cyclic peptides with lactam bridges (with seven amino acids) was prepd. on an automatic peptide synthesizer. We demonstrate that the Guibe 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 prepg. long cyclic peptides on a resin. We have also manually synthesized a cyclic glucagon analog contg. 24 amino acid residues. These results demonstrated that properly controlled palladium-mediated deprotection of Allyl/Alloc protecting groups can be used to prep. cyclic peptides on the resin using an automated peptide synthesizer and cyclic peptides with a long chainKeywords
This publication has 28 references indexed in Scilit:
- Use of Alloc-amino acids in solid-phase peptide synthesis. Tandem deprotection-coupling reactions using neutral conditionsPublished by Elsevier ,1998
- HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and GlycopeptidesThe Journal of Organic Chemistry, 1997
- A Novel Allylic Anchor for Solid‐Phase Synthesis—Synthesis of Protected and Unprotected O‐Glycosylated Mucin‐Type GlycopeptidesAngewandte Chemie International Edition in English, 1995
- Allyl‐based groups for side‐chain protection of amino‐acidsInternational Journal of Peptide and Protein Research, 1993
- FMOC solid phase synthesis of an endothelin converting enzyme substrateInternational Journal of Peptide and Protein Research, 1992
- Potent and prolonged-acting cyclic lactam analogs of .alpha.-melanotropin: design based on molecular dynamicsJournal of Medicinal Chemistry, 1989
- Applications of BOP reagent in solid phase synthesisInternational Journal of Peptide and Protein Research, 1988
- Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesisThe Journal of Organic Chemistry, 1987
- Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)]Angewandte Chemie International Edition in English, 1987
- Synthesis of side‐chain to side‐chain cyclized peptide analogs on solid supportsInternational Journal of Peptide and Protein Research, 1985