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Efficient Synthesis of Antigenic Trisaccharides Containing N ‐Acetylglucosamine: Protection of NHAc as NAc 2
Author(s) -
Tsutsui Masato,
Sianturi Julinton,
Masui Seiji,
Tokunaga Kento,
Manabe Yoshiyuki,
Fukase Koichi
Publication year - 2020
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.201901809
Subject(s) - chemistry , n acetylglucosamine , diacetyl , glycosylation , epitope , acetylglucosamine , acetylation , reactivity (psychology) , glucosamine , antigen , oligosaccharide , glycan , glycoprotein , biochemistry , stereochemistry , combinatorial chemistry , enzyme , immunology , medicine , alternative medicine , pathology , gene , biology
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 NAc 2 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 NAc 2 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.
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