4-Methoxybenzyloxymethyl group as an N π-protecting group for histidine to eliminate side-chain-induced racemization in the Fmoc strategy

The search for a new Fmoc-His derivative that displays no racemization in activating and coupling steps showed that the MBom ( N π-MBom) group possessed all of the chemical properties required for Fmoc chemistry. The 4-methoxybenzyloxymethyl (MBom) group was introduced at the N π-position of histidi...

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Bibliographic Details
Published in:Tetrahedron letters 2011-09, Vol.52 (38), p.4947-4949
Main Authors: Hibino, Hajime, Nishiuchi, Yuji
Format: Article
Language:English
Subjects:
4-Methoxybenzyloxymethyl (MBom) group
Histidine
Protecting group
Racemization
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Summary:The search for a new Fmoc-His derivative that displays no racemization in activating and coupling steps showed that the MBom ( N π-MBom) group possessed all of the chemical properties required for Fmoc chemistry. The 4-methoxybenzyloxymethyl (MBom) group was introduced at the N π-position of histidine, and its utility was examined under the conditions for peptide synthesis by Fmoc strategy. The N π-MBom group proved to prevent the risk of racemization during incorporation of the His residue and to possess all of the chemical properties required for Fmoc chemistry. The side reaction associated with formaldehyde generated from the N π-MBom group upon acidolysis could be effectively prevented by performing the standard TFA treatment in the presence of methoxyamine·hydrochloride (MeONH 2·HCl).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.07.065