title: Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose conjugates linked by direct B-O-C bonds.
abstract: We report the first O-BODIPY-glucose conjugates, in which the sugar is directly attached to the BODIPY boron through covalent B-O-C bonds. The reaction of Cl-BODIPY with glucose in acetonitrile produced the 1 : 1 α-glucofuranose BODIPY (1), 1 : 2 α-glucofuranose BODIPY (2) and 1 : 2 α-glucoseptanose BODIPY (3) esters. Compound 3 is a rare instance of the unnatural septanose form of glucose, and the first example of a septanose borate.
authors.affiliation: School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand. p.brothers@auckland.ac.nz.
authors.forename: Bowen
authors.initials: B
authors.lastname: Liu
authors.forename: Nina
authors.initials: N
authors.lastname: Novikova
authors.forename: M Cather
authors.initials: MC
authors.lastname: Simpson
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.forename: Tilo
authors.initials: T
authors.lastname: Söhnel
authors.forename: David C
authors.initials: DC
authors.lastname: Ware
authors.forename: Penelope J
authors.initials: PJ
authors.lastname: Brothers
mesh_terms: D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002244:Carbon / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D008958:Models, Molecular; D010100:Oxygen / Q000737:chemistry*; D000073893:Sugars / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D005663:Furans; D000073893:Sugars; D002244:Carbon; D005947:Glucose; D001895:Boron; D010100:Oxygen