title: Utilization of the Heavy Atom Effect for the Development of a Photosensitive 8-Azacoumarin-Type Photolabile Protecting Group.
abstract: A remarkable improvement of the photochemical properties of coumarin-type photolabile protecting groups was achieved by iodine substitution. The newly identified 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged acetate showed excellent photolytic efficiency, significantly higher than that of the corresponding bromine-containing coumarin- and azacoumarin-type caging groups. The results provide a solid approach to improving the photosensitivity of photolabile protecting groups.
authors.affiliation: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Takano
authors.affiliation: Department of Applied Chemistry and Biochemical Engineering, Faculty of Engineering, Shizuoka University , Hamamatsu, Shizuoka 432-8561, Japan.
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Narumi
authors.affiliation: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Nomura
authors.affiliation: Department of Biomaolecular Science, Toho University , Funabashi, Chiba 274-8510, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Furuta
authors.affiliation: Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tamamura
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010782:Photolysis; D013449:Sulfonamides
chemical_list: D001372:Aza Compounds; D003374:Coumarins; D013449:Sulfonamides; C064991:N-(8-aminohexyl)-5-iodonaphthalene-1-sulfonamide; C030123:coumarin