Modular Synthesis of Nona‐Decasaccharide Motif from <i>Psidium guajava</i> Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy

Zhang, Yunqin; Chen, Zixi; Huang, Yingying; He, Shaojun; Yang, Xingkuan; Wu, Zhibing; Wang, Xiufang; Xiao, Guozhi

doi:10.1002/ange.202000992

Cited by 8 publications

(2 citation statements)

References 43 publications

(31 reference statements)

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“…While one-pot glycosylation protocol emerges as versatile strategy to synthesize complex oligo/polysaccharides of which the units are tethered by acetal linkages [49][50][51] , this strategy is not applicable to the assembly of conventionally synthesized bis-glycosyl phosphodiester which incorporate reactive functionality of phosphate anion. Gratifyingly, bis-glycosyl benzyl phosphotriesters readily prepared in our system could serve as attractive substrates for one-pot glycosylation, and described in Scheme 3 is an example, in which linker-tethered 5 was assembled in one pot via gold(I)-catalyzed glycosylation reaction and a follow-up orthogonal coupling promoted by NIS and TMSOTf.…”

Section: Scheme 2 Synthesis Of Phosphoglycopeptidementioning

confidence: 99%

A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

Zhu

Zhang

Yang

et al. 2021

Preprint

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A highly efficient and stereoselective approach to the synthesis of biologically important and complex α-glycosyl phosphosaccharides (GPSs) has been disclosed, employing direct gold(I)-catalyzed glycosylation of the weakly nucleophilic phosphoric acid acceptors. The broad substrate scope is demonstrated with more than 45 examples, including glucose (Glc), xylose, glucouronatose, galactose (Gal), mannose (Man), rhamnose (Rha), fucose (Fuc), 2-N3-2-dexoxymannose (ManN3), 2-N3-2-dexoxyglucose (GlcN3), 2-N3-2-dexoxygalactose (GalN3) and unnatural carbohydrates. Moreover, the glycosyl phosphotriester prepared herein was successfully applied to the one-pot synthesis of a GPS from Leishmania donovani, and an effective preparation of a trisaccharide diphosphate of GPS fragments from Hansenula capsulate via iterative elongation strategy is realized.

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Section: Scheme 2 Synthesis Of Phosphoglycopeptidementioning

confidence: 99%

A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

Zhu

Zhang

Yang

et al. 2021

Preprint

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“…[9] However, due to regio-and stereoselective issues, [10] the efficient synthesis of long, branched, and complex glycans with many 1,2-cis glycosidic linkages remains a formidable task. [11][12][13][14][15] Herein, we highlight the recent chemical synthesis and functional studies of LPS from the commensal gut microbiota, including Bacteroides vulgatus [16] (Figure 1B) and gut-associated lymphoid-tissue-resident Alcaligenes faecalis [17] (Figure 1C).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Chemical Synthesis of Structural Domains of Lipopolysaccharides from the Commensal Gut‐Associated Microbiota

Wang,

Xiao

2023

ChemBioChem

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Lipopolysaccharides from the commensal gut‐associated microbiota are interesting biomolecules for the treatment of various inflammatory diseases. Different from pathogenic lipopolysaccharides, commensal lipopolysaccharides have distinct chemical structures and mediate beneficial homeostasis with the immune system of host. However, the accessibility issues of homogenous and pure commensal lipopolysaccharides hampered the in‐depth studies of their functions. In this concept article, we highlight the recent synthesis of lipopolysaccharides from gut‐associated lymphoid‐tissue‐resident Alcaligenes faecalis and Bacteroides vulgatus, which hopes to inspire the more efforts devoting to this fantastic biomolecules.

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Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of α‐Glycans up to a 30‐mer

Zhang

Chen

et al. 2021

Angewandte Chemie

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The efficient synthesis of long, branched, and complex carbohydrates containing multiple 1,2‐cis glycosidic linkages is a long‐standing challenge. Here, we report a merging reagent modulation and 6‐O‐levulinoyl remote anchimeric assistance glycosylation strategy, which is successfully applied to the first highly stereoselective synthesis of the branched Dendrobium Huoshanense glycans and the linear Longan glycans containing up to 30 contiguous 1,2‐cis glucosidic bonds. DFT calculations shed light on the origin of the much higher stereoselectivities of 1,2‐cis glucosylation with 6‐O‐levulinoyl group than 6‐O‐acetyl or 6‐O‐benzoyl groups. Orthogonal one‐pot glycosylation strategy based on glycosyl ortho‐alkynylbenzoates and ortho‐(1‐phenylvinyl)benzoates has been demonstrated in the efficient synthesis of complex glycans, precluding such issues as aglycon transfer inherent to orthogonal one‐pot synthesis based on thioglycosides.

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Modular Synthesis of Nona‐Decasaccharide Motif from Psidium guajava Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy

Cited by 8 publications

References 43 publications

A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

Recent Advances in Chemical Synthesis of Structural Domains of Lipopolysaccharides from the Commensal Gut‐Associated Microbiota

Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of α‐Glycans up to a 30‐mer

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