title: Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives.
abstract: The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK.
authors.forename: Alexander G
authors.initials: AG
authors.lastname: Russell
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Sadler
authors.forename: Helen J
authors.initials: HJ
authors.lastname: Laidlaw
authors.forename: Agustín
authors.initials: A
authors.lastname: Gutiérrez-Loriente
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Wharton
authors.forename: David
authors.initials: D
authors.lastname: Carteau
authors.forename: Dario M
authors.initials: DM
authors.lastname: Bassani
authors.forename: John S
authors.initials: JS
authors.lastname: Snaith
mesh_terms: D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D010782:Photolysis; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009574:Nitro Compounds; C553213:alpha-carboxy-6-nitroveratryl; D014443:Tyrosine