title: 4-Methoxybenzyloxymethyl group, a racemization-resistant protecting group for cysteine in Fmoc solid phase peptide synthesis.
abstract: The 4-methoxybenzyloxymethyl (MBom) group was introduced for sulfhydryl protection of Cys in combination with Fmoc chemistry. The MBom group proved to substantially suppress racemization of Cys during its incorporation mediated by phosphonium or uronium reagents. Furthermore, this group was found to significantly reduce racemization of the C-terminal Cys linked to a hydroxyl resin during repetitive base treatment, in comparison with the usually used trityl (Trt) and acetamidomethyl (Acm) groups.
authors.affiliation: SAITO Research Center, Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
authors.forename: Hajime
authors.initials: H
authors.lastname: Hibino
authors.forename: Yuji
authors.initials: Y
authors.lastname: Nishiuchi
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005449:Fluorenes; D010455:Peptides; D003545:Cysteine