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A compact trialkyne platform with a silyl-protected 1,3-butadiynyl sulfide moiety and a terminal alkyne group has been developed for sequential regioselective transition metal-catalyzed triazole formation reactions with three azides. This method enabled the facile construction of a low-molecular-weight triazole library and the synthesis of middle-molecular-weight trifunctional probes for protein modification. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

Front Cover: Efficient Synthesis of Antigenic Trisaccharides Containing N-Acetylglucosamine: Protection of NHAc as NAc2 (Eur. J. Org. Because NAc SB 2 sb protected fragments cannot form intermolecular hydrogen bonding, this strategy can improve the reactivity in glycosylation to realize the efficient construction of glycans. Because NAc SB 2 sb protected fragments cannot form intermolecular hydrogen bonding, this strategy can improve the reactivity in glycosylation to realize the efficient construction of glycans. [Extracted from the article]

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. [ABSTRACT FROM AUTHOR]

Cancer treatment with antibodies (Abs) is one of the most successful therapeutic strategies for obtaining high selectivity. In this study, α-gal-Ab conjugates were developed that dramatically increased cellular cytotoxicity by recruiting natural Abs through the interaction between α-gal and anti-gal Abs. The potency of the α-gal-Ab conjugates depended on the amount of α-gal conjugated to the antibody: the larger the amount of α-gal introduced, the higher the level of cytotoxicity observed. The conjugation of antibodies with an α-gal dendrimer allowed the introduction of large amounts of α-gal to the Ab, without loss of affinity for the target cell. The method described here will enable the re-development of Abs to improve their potency., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)