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Fmoc-L-His(MBom)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-pi-(4-methoxybenzyloxymethyl)-L-histidine // Synonyms: Fmoc-His(MBom)-OH, (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-((4-methoxybenzyloxy)methyl)-1H-imidazol-5-yl)propanoic acid
- Product code:FAA7530
- CAS No.:1327338-56-6
- Formula:C30H29N3O6
- Storage temperature:-20°C
- Molecular weight:527.57 g/mol
from $487.50
description
MBom (4-Methoxybenzyloxymethyl) as protecting group on the pi position of the imidazole ring of histidine was found to prevent side-chain-induced racemization during incorporation of the His residue even at elevated temperature, as in the case of MW-assisted SPPS. Furthermore, at low acidic conditions, like 1% TFA in DCM or AcOH/TFE/DCM (1:1:3) MBom remains fully detached to histidine, while standard protecting group tau-trityl already is partially being cleaved. Back alkylation of MBom is being prevented by addition of scavengers, e.g. Reagent K (TFA/water/phenol/thioanisole/EDT [82.5:5:5:5:2.5]) or with MeONH2*HCl and addition of thiophenol.
references
Synthesis and application of N-alpha-Fmoc-N-pi-4-methoxybenzyloxymethylhistidine in solid phase peptide synthesis; Hajime Hibino, Yasuyoshi Miki and Yuji Nishiuchi; J. Pept. Sci. 2012; 18: 763–769. DOI 10.1002/psc.2464
4-Methoxybenzyloxymethyl group as an N-pi-protecting group for histidine to eliminate side-chain-induced racemization in the Fmoc strategy; Hajime Hibino and Yuji Nishiuchi, Tetrahedron Lett. 2011; 52: 4947-4949. DOI: 10.1016/j.tetlet.2011.07.065
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