A Divergent Method to Prepare 5‐Amino‐, 5‐N‐Acetamido‐, and 5‐N‐Glycolylsialosides. Issue 24 (12th July 2013)

• Record Type: Journal Article
• Authors: Boltje, Thomas J.; Heise, Torben; Rutjes, Floris P. J. T.; van Delft, Floris L.
• Is Part Of: European journal of organic chemistry. Issue 24(2013)
• Page Start: 5257
• Page End: 5261
• Publication Date: 2013-07-12
• Subjects: Natural products -- Carbohydrates -- Sialosides -- Sialic acids -- Glycosylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300664
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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. Herein, we report a divergent chemical approach to enable the synthesis of the aforementioned 5‐ N ‐substituted sialosides by using a single sialic acid building block.