153140-16-0

2-Aminopyridine derivatives having a bifunctional or unifunctional structure and capable of serving as reactants in synthetically converting organic compounds, such as carbohydrates, proteins, lipids or polymer resins, to desired conjugated structures sui

2-Aminopyridine derivatives having a bifunctional or unifunctional structure and capable of serving as reactants in synthetically converting organic compounds, such as carbohydrates, proteins, lipids or polymer resins, to desired conjugated structures suited for various purposes and detectable by fluorescence spectrometry with high sensitivity, a fluorescent labeling agent comprising the same, and methods of their production are disclosed.

New bifunctional reagents, 2-amino-6-carboxyethylpyridine and 2-amino-6-cyanoethylpyridine, were designed and synthesized in order to provide a novel procedure for preparation of neoglycoconjugates from fluorescence-labeled and purified sugar chains.Labeling of model sugar chains with these reagents was effected by reductive amination using BH3*Me2NH to give corresponding 6-carboxyethylpyridylaminated (CEPA-) and 6-cyanoethylpyridylaminated (CNEPA-) derivatives, which were readily purified by reversed phase HPLC.The reagent parts of the labeled products possess the functional groups which then serve as linkers for coupling with matrices such as proteins and polymers.A CEPA-derivative of glucose was directly coupled with the ε-amino group of a Lys derivative to give a neoglycoprotein model.CNEPA-sugars were hydrogenated to give 6-aminopropylpyridylaminated (APPA-) derivatives, which can then be readily used for the preparation of various types of neoglycoconjugates by use of appropriate spacers as exemplified by the coupling of APPA-maltotriose with bovine serum albumin (BSA), biotin, and acrylic acid.The reaction of APPA-maltotriose with succinimidyl 3-(3-nitro-2-pyridyldithio)propionate gave the corresponding amide to be used for a disulfide formation with BSA.Condensation with biotin was effected by use of N-hydroxysuccinimidobiotin.The conjugation of APPA-maltotriose with acrylic acid was carried out by use of 4-acryloyloxyphenyldimethylsulfonium methylsulfate to give the corresponding acrylamide, which can be used for the preparation of sugar-acrylamide copolymers.