Efficient Synthesis of Antigenic Trisaccharides Containing N‐Acetylglucosamine: Protection of NHAc as NAc2

The antigenic trisaccharides, α‐gal epitope and H antigen, containing N‐acetyl‐d‐glucosamine (GlcNAc) were synthesized using a diacetyl strategy, in which NHAc is tentatively converted to NAc2 during oligosaccharide construction. Acetylation of NHAc in GlcNAc significantly improved the reactivity in...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-03, Vol.2020 (12), p.1802-1810
Main Authors: Tsutsui, Masato, Sianturi, Julinton, Masui, Seiji, Tokunaga, Kento, Manabe, Yoshiyuki, Fukase, Koichi
Format: Article
Language:English
Subjects:
Acetylation
Antigens
Elongation
Glycan antigen
Glycosylation
Hydrogen bonds
Microflow
Oligosaccharides
Protecting groups
Strategy
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Summary:The antigenic trisaccharides, α‐gal epitope and H antigen, containing N‐acetyl‐d‐glucosamine (GlcNAc) were synthesized using a diacetyl strategy, in which NHAc is tentatively converted to NAc2 during oligosaccharide construction. Acetylation of NHAc in GlcNAc significantly improved the reactivity in glycosylation reactions. The diacetyl strategy allowed to achieve the efficient synthesis of α‐gal through a sequential one‐pot and one‐flow procedure. Meanwhile, H antigen was synthesized by stepwise elongation from the reducing end side of GlcNAc. The enhancement of the reactivity by NAc2 protection was observed in both glycosylations at proximal and distal positions to GlcNAc. This diacetyl strategy is expected to be applicable to the synthesis of a wide range of glycans. Acetamide (NHAc) is tentatively converted to diacetylimide (NAc2) during oligosaccharide construction. Formation of hydrogen bonds through NHAc in GlcNAc was confirmed by NMR measurements, and N,N‐diacetyl protection improved the reactivity in glycosylation to realize the efficient construction of glycans.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901809