title: Synthesis of a 3'-naphthamido-LacNAc fluorescein conjugate with high selectivity and affinity for galectin-3.
abstract: Described is the synthesis of a fluorescent LacNAc derivative appended with a 3'-deoxy-3'-naphthamido functionality, 2-(fluorescein-5/6-amido)ethyl 3-deoxy-3-(2-naphthamido)-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside, which confers high affinity (Kd 170 nM) and selectivity for galectin-3 via a stacking interaction with Arg144. Its use as a selective and sensitive galectin-3 probe is demonstrated with fluorescence polarization measurements.
authors.affiliation: Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Karolina
authors.initials: K
authors.lastname: Aplander
authors.forename: Johan
authors.initials: J
authors.lastname: Tejler
authors.forename: Jörgen
authors.initials: J
authors.lastname: Toftered
authors.forename: Susanne
authors.initials: S
authors.lastname: Carlsson
authors.forename: Barbro
authors.initials: B
authors.lastname: Kahl-Knutsson
authors.forename: Anders
authors.initials: A
authors.lastname: Sundin
authors.forename: Hakon
authors.initials: H
authors.lastname: Leffler
authors.forename: Ulf J
authors.initials: UJ
authors.lastname: Nilsson
mesh_terms: D004187:Disaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D005452:Fluoresceins / Q000138:chemical synthesis* / Q000378:metabolism; D005454:Fluorescence Polarization; D037502:Galectin 3 / Q000032:analysis / Q000378:metabolism*
chemical_list: D004187:Disaccharides; D005452:Fluoresceins; D037502:Galectin 3