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N ‐Carboxymethylated 6,7‐Dimethoxy‐4‐trifluoromethylcarbostyrils as Fluorescence Markers for Amino Acids, Peptides, Amino Carbohydrates and Amino Polysaccharides
Author(s) -
Badgujar Naresh S.,
Pazicky Marek,
Traar Pedro,
Terec Anamaria,
Uray Georg,
Stadlbauer Wolfgang
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500981
Subject(s) - chemistry , fluorescence , saponification , amino acid , aqueous solution , polysaccharide , aqueous medium , organic chemistry , peptide , biochemistry , physics , quantum mechanics
The highly fluorescent 6,7‐dimethoxy‐3‐trifluoromethylcarbostyril 2 was regioselectively carboxymethylated with bromoacetates 4 at N‐1 to give esters of type 5 in good yield. After saponification to 8 , succinimidoyl (OSu) esters 9 were prepared. Dyestuffs 9 were reacted in slightly basic aqueous media under mild conditions with free amino acids, esters and peptides to give the fluorescently labeled amino acid derivatives 11 and 13 in good yields. Similarly, aminoglucose and chitosane reacted to form the fluorescently labeled carbohydrates 15 and 17 . Fluorescence quantum yields of 0.3–0.4, their photostability and a pH‐independence between 3 and 10 make this class of compounds useful for linking to biological samples in aqueous media.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)