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Wang J, Lan X, Zhang S, Cai C, Zhang Q, Feng Y, Chai Y
S-o-( p-Methoxyphenylethynyl)benzyl (SMPEB) Glycosides for Catalytic Glycosylation and Their Application in the Synthesis of Polyporus Umbellatus Polysaccharides
Organic Letters 25(33) (2023)
6116-6121
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b-D-Glcp-(1-3)-+ b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
| |
b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp |
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Polyporus umbellatus
(NCBI TaxID 158314,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
NCBI PubMed ID: 37578318Publication DOI: 10.1021/acs.orglett.3c02072Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Y. Feng < fengyingle
snnu.edu.cn>; Y. Chai <ychai
snnu.edu.cn>
Institutions: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Xi'an, Shaanxi 710119, P. R. China, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi 710119, P. R. China
We herein reported a new type of S-o-(p-methoxyphenylethynyl)benzyl donor for a highly efficient glycosylation method. The donor was activated by 10% Tf2O and underwent glycosylation with various acceptors to provide the corresponding glycosides in excellent yield. Furthermore, two repetitive fragments of Polyporus umbellatus polysaccharides (PUPs), isolated from traditional Chinese medicine 'Polyporus umbellatus', were prepared by combining the 'single-catalyst one-pot' and 'latent-active' strategies for the first time for future clear studies on the structure-activity relationship of PUPs.
synthesis, polysaccharides, structure-activity relationship, glycosylation, Polyporus umbellatus
Structure type: fragment of a bigger structure
Location inside paper: graphical abstract, decasaccharide fragment of RU
Trivial name: Polyporus umbellatus polysaccharide
Methods: 13C NMR, 1H NMR, NMR-2D, IR, chemical synthesis, optical rotation measurement, HR-ESI-MS, сolumn chromatography, catalytic glycosylation
Comments, role: decasaccharide fragment of Polyporus umbellatus polysaccharide
Related record ID(s): 41509
NCBI Taxonomy refs (TaxIDs): 158314
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Wang J, Lan X, Zhang S, Cai C, Zhang Q, Feng Y, Chai Y
S-o-( p-Methoxyphenylethynyl)benzyl (SMPEB) Glycosides for Catalytic Glycosylation and Their Application in the Synthesis of Polyporus Umbellatus Polysaccharides
Organic Letters 25(33) (2023)
6116-6121
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp |
Show graphically |
Polyporus umbellatus
(NCBI TaxID 158314,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
NCBI PubMed ID: 37578318Publication DOI: 10.1021/acs.orglett.3c02072Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Y. Feng < fengyingle
snnu.edu.cn>; Y. Chai <ychai
snnu.edu.cn>
Institutions: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Xi'an, Shaanxi 710119, P. R. China, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi 710119, P. R. China
We herein reported a new type of S-o-(p-methoxyphenylethynyl)benzyl donor for a highly efficient glycosylation method. The donor was activated by 10% Tf2O and underwent glycosylation with various acceptors to provide the corresponding glycosides in excellent yield. Furthermore, two repetitive fragments of Polyporus umbellatus polysaccharides (PUPs), isolated from traditional Chinese medicine 'Polyporus umbellatus', were prepared by combining the 'single-catalyst one-pot' and 'latent-active' strategies for the first time for future clear studies on the structure-activity relationship of PUPs.
synthesis, polysaccharides, structure-activity relationship, glycosylation, Polyporus umbellatus
Structure type: fragment of a bigger structure
Location inside paper: graphical abstract, nonasaccharide fragment of RU
Trivial name: Polyporus umbellatus polysaccharide
Methods: 13C NMR, 1H NMR, NMR-2D, IR, chemical synthesis, optical rotation measurement, HR-ESI-MS, сolumn chromatography, catalytic glycosylation
Comments, role: nonasaccharide fragment of Polyporus umbellatus polysaccharide
Related record ID(s): 41093
NCBI Taxonomy refs (TaxIDs): 158314
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There is only one chemically distinct structure:
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