title: Bichromophoric fluorescent photolabile protecting group for alcohols and carboxylic acids.
abstract: Novel bichromophoric fluorescent photolabile protecting group, (5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl (DNS-NQMP), allows for the independent photochemical release and fluorescent imaging of caged substrates. Irradiation of DNS-NQMP-caged alcohols and carboxylic acids with 300 or 350 nm light results in fast (k(release) ~ 10(5) s(-1)), efficient (Φ = 0.2), and quantitative release of the substrates. This uncaging chemistry is compatible with aqueous media and DNS-NQMP-protected hydroxy compounds are hydrolytically stable at neutral pH. Upon excitation with 400 nm light, caged compounds show intense green emission (λ(max) = 559 nm) with 21% fluorescence quantum yield. Fluorescent readout conducted using 400 nm or longer wavelengths does not cause substrate release. The DNS-NQMP chromophore retains its fluorescent properties after photo-uncaging reaction.
authors.affiliation: Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
authors.forename: Selvanathan
authors.initials: S
authors.lastname: Arumugam
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Popik
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D005453:Fluorescence; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D010782:Photolysis
chemical_list: C574903:(5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl; D000438:Alcohols; D002264:Carboxylic Acids; D009281:Naphthalenes