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Fmoc-L-His(MBom)-OH
Nom chimique: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-pi-(4-methoxybenzyloxymethyl)-L-histidine // Synonymes: Fmoc-His(MBom)-OH, (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-((4-methoxybenzyloxy)methyl)-1H-imidazol-5-yl)propanoic acid
- n° Art.:FAA7530
- n° CAS:1327338-56-6
- Formule:C30H29N3O6
- Storage temperature:-20°C
- Masse moléculaire:527,57 g/mol
from 390,00 €
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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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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