TY - JOUR
T1 - Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy
T2 - Potential for library synthesis
AU - Grieco, P.
AU - Gitu, P. M.
AU - Hruby, V. J.
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
KW - Allyl/Alloc strategy
KW - Automated synthesis
KW - Cyclic peptides
KW - Side-chain-to-side-chain cyclization
KW - Solid-phase synthesis
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U2 - 10.1111/j.1399-3011.2001.00816.x
DO - 10.1111/j.1399-3011.2001.00816.x
M3 - Article
C2 - 11298927
AN - SCOPUS:0035078547
SN - 1747-0277
VL - 57
SP - 250
EP - 256
JO - Chemical Biology and Drug Design
JF - Chemical Biology and Drug Design
IS - 3
ER -