| 17803257 |
Taniguchi A, Yoshiya T, Abe N, Fukao F, Sohma Y, Kimura T, Hayashi Y, Kiso Y: 'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. J Control Release. 2008 May 8;127(3):267-72. Epub 2008 Feb 15.
'O-Acyl isopeptide method' is an efficient synthetic method for peptides. We designed 'O-acyl isodipeptide units', Boc-Ser/Thr (Fmoc-Xaa)-OH, as important building blocks to enable routine use of the O-acyl isopeptide method. In the synthesis of an Abeta1-42 isopeptide using O-acyl isodipeptide unit Boc-Ser (Fmoc-Gly)-OH, a side reaction, resulting in the deletion of Ser (26) in the O-acyl isopeptide structure, was noticed during coupling of the unit. We observed that the side reaction occurred during the activation step and was solvent-dependent. In DMF or NMP, an intramolecular side reaction, originating from the activated species of the unit, occurred during the activation step. In non-polar solvents such as CHCl (3) or CH (2) Cl (2), the side reaction was less likely to occur. Using CH (2) Cl (2) as solvent in coupling the unit, the target Abeta1-42 isopeptide was synthesized with almost no major side reaction. |
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