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A Divergent Method to Prepare 5‐Amino‐, 5‐ N ‐Acetamido‐, and 5‐ N ‐Glycolylsialosides
Author(s) -
Boltje Thomas J.,
Heise Torben,
Rutjes Floris P. J. T.,
van Delft Floris L.
Publication year - 2013
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.201300664
Subject(s) - chemistry , sialic acid , substituent , homogeneous , amine gas treating , block (permutation group theory) , stereochemistry , chemical synthesis , combinatorial chemistry , amino acid , biochemistry , organic chemistry , in vitro , physics , geometry , mathematics , thermodynamics
Sialic acids are essential mediators of biological processes involving carbohydrate recognition. A major determinant of sialic acid recognition is the N‐5 substituent, which can be an N ‐acetyl (human), N ‐glycolyl (non‐human), or amine (cancer associated) functionality. Access to homogeneous sialosides with distinct substitution patterns is essential to determine structure–activity relationships. Herein, we report a divergent chemical approach to enable the synthesis of a library of specifically substituted sialosides by using a single sialic acid building block.