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Synthesis of Fluorescence‐Labelled Glycosidic Prodrugs Based on the Cytotoxic Antibiotic Duocarmycin
Author(s) -
Tietze Lutz F.,
Behrendt Frank,
Major Felix,
Krewer Birgit,
von Hof J. Marian
Publication year - 2010
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.201000966
Subject(s) - chemistry , succinimides , glycosidic bond , prodrug , stereochemistry , fluorescence , ring (chemistry) , combinatorial chemistry , organic chemistry , biochemistry , physics , quantum mechanics , enzyme
The synthesis of the glycosidic prodrugs (1 S )‐ 30a , (1 S ,10 R )‐ 30b and (1 S ,10 R )‐ 32 labelled with different fluorescence dyes at different positions at the aromatic A‐ring in 2 is described; the compounds are structurally based on the cytotoxic antibiotic duocarmycin SA. For binding, the amino compounds (1 S )‐ 3a and (1 S ,10 R )‐ 3b were treated with the commercially available succinimides of the dyes 5‐SFX ( 29 ) and D10162 ( 31 ), respectively.