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102. N-Carboxymethylated 6,7-Dimethoxy-4-trifluoromethylcarbostyrils As Fluorescence Markers for Amino Acids, Peptides, Amino Carbohydrates and Amino Polysaccharides
N. S. Badgujar, M. Pazicky, P. Traar, A. Terec, G. Uray, W. Stadlbauer, Eur. J. Org. Chem., 2006, 2715-2722

Abstract:
The highly fluorescent 6,7-dimethoxy-3-trifluoromethylcarbostyril 2 could be 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 reacted in slightly basic aqueous media under mild conditions with free amino acids, their esters and with peptides to give fluorescence labeled amino acid derivatives 11 and 13 in good yields. Similar, aminoglucose and chitosane reacted to fluorescence labeled carbohydrates 15 and 17. Fluorescence quantum yields of 0.3-0.4, their photostability and pH independence between 3 and 10 make this class of compounds useful for linking to biological samples in aqueous media.


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