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Synthesis and Hydrolytic Stability of N ‐ and O ‐Methyloxyamine Linkers for the Synthesis of GlycoconjugatesSynthesis and Hydrolytic Stability of N ‐ and O ‐Methyloxyamine Linkers for the Synthesis of Glycoconjugates
Author(s) -
Munneke Stefan,
Hill Jaimé C.,
Timmer Mattie S. M.,
Stocker Bridget L.
Publication year - 2017
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.201601534
Subject(s) - chemistry , hydrolysis , linker , glycan , combinatorial chemistry , glycoconjugate , stereochemistry , organic chemistry , biochemistry , computer science , glycoprotein , operating system
A comparison of the merits of N ‐ and O ‐methyloxyamines as linkers for carbohydrates is presented for the first time. In particular, optimized synthetic routes for each linker type are given, and the ease of glycan conjugation is described. The hydrolytic stabilities of the respective oxyamine glycoconjugates under a variety of different conditions are reported. This provides insight into the factors that influence hydrolysis rates, and sheds light on the acid‐catalysed hydrolysis mechanism.