Allyloxycarbonyl group
Allyloxycarbonyl group: chlorocarbonic acid allyloxy ester (Alloc-Cl, above), as well as the general formula of an Alloc-protected primary amine (middle) and Alloc-protected glycine (below). The allyloxycarbonyl residue is marked in blue ; R is an organyl radical ( alkyl radical, aryl radical, alkylaryl radical, etc.).
The allyloxycarbonyl group , usually abbreviated to Alloc in specialist circles , is similar to the benzyloxycarbonyl group (Cbz group) and is used as a protective group in the chemical synthesis of peptides .
The Alloc protective group is used to protect α-amino groups, but also to protect side groups, especially in the synthesis of cyclic peptides. The Alloc protecting group is stable under basic and acidic conditions and can be split off by the action of tetrakis (triphenylphosphine) palladium (0) and a suitable nucleophile.
The Alloc group is mostly used as a chlorocarbonic acid ester to protect amino groups.
Individual evidence
- ↑ Sherine N. Khattab, Ramon Subirós-Funosas, Ayman El-Faham, Fernando Albericio: O xime Carbonates: Novel Reagents for the Introduction of Fmoc and Alloc Protecting Groups, Free of Side Reactions , Eur. J. Org. Chem. 2010 , 3275-3280.
- ↑ P. Gómez-Martinez, M. Dessolin, F. Guibé, F. Albericio, J. Chem. Soc. Perkin Trans. I 1999 , 2871-2874.