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. Issue 25 (19th April 2017)

• Record Type: Journal Article
• Authors: Munneke, Stefan; Hill, Jaimé C.; Timmer, Mattie S. M.; Stocker, Bridget L.
• Is Part Of: European journal of organic chemistry. Issue 25(2017)
• Page Start: 3722
• Page End: 3728
• Publication Date: 2017-04-19
• Subjects: Carbohydrates -- Glycoconjugates -- Conjugation -- Oxyamines -- Hydrolysis -- Reaction mechanisms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601534
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : A direct comparison of N ‐ vs. O ‐methyloxyamine linkers for carbohydrates is presented, including optimised synthetic routes, glycan conjugations, and studies into hydrolytic stabilities. We demonstrate that pH, glycan concentration, and buffer strength influence hydrolysis rates, and provide insight into the acid‐catalysed hydrolysis mechanism.