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Ma Y, Jiang Q, Wang X, Xiao G
Total Synthesis of Cordyceps militaris Glycans via Stereoselective Orthogonal One-Pot Glycosylation and α-Glycosylation Strategies
Organic Letters 24(43) (2022)
7950-7954
|
a-D-Glcp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-+ b-D-Galp-(1-4)-a-D-Glcp-(1-3)-+
| |
-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1- |
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Cordyceps militaris
(NCBI TaxID 73501,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 36286593Publication DOI: 10.1021/acs.orglett.2c03081Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: G. Xiao <xiaoguozhi
mail.kib.ac.cn>
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Kunming 650201, China, Department of Chemistry, Kunming University, 2 Puxing Road, Kunming 650214, China
Cordyceps militaris glycans with potent antioxidant activities have been efficiently and collectively synthesized. The synthetic approach features the following: (1) a stereoselective orthogonal one-pot glycosylation strategy for both 1,2-trans- and 1,2-cis-glycosidic linkages; (2) a merged reagent modulation and remote anchimeric assistance (RMRAA) α-glucosylation strategy; (3) DMF-modulated α-glucosylation; (4) convergent [3 + 4 + 6] orthogonal one-pot assembly of the target tridecasaccharide.
synthesis, glycan, glycosylation, Antioxidant activity, Cordyceps militaris
Structure type: polymer chemical repeating unit
Location inside paper: scheme 1(A)
Trivial name: polysaccharide P70-1
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_142487,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153201,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_156493,IEDB_190606,IEDB_76933,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_198,SB_44,SB_6,SB_67,SB_7,SB_72,SB_88
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical synthesis, glycosylation, optical rotation measurement, orthogonal one-pot glycosylation
Related record ID(s): 51789
NCBI Taxonomy refs (TaxIDs): 73501
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There is only one chemically distinct structure:
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Ma Y, Jiang Q, Wang X, Xiao G
Total Synthesis of Cordyceps militaris Glycans via Stereoselective Orthogonal One-Pot Glycosylation and α-Glycosylation Strategies
Organic Letters 24(43) (2022)
7950-7954
|
a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-+ b-D-Galp-(1-4)-a-D-Glcp-(1-3)-+
| |
a-D-Glcp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1--/(CH2)5NH2/ |
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Cordyceps militaris
(NCBI TaxID 73501,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 36286593Publication DOI: 10.1021/acs.orglett.2c03081Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: G. Xiao <xiaoguozhi
mail.kib.ac.cn>
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Kunming 650201, China, Department of Chemistry, Kunming University, 2 Puxing Road, Kunming 650214, China
Cordyceps militaris glycans with potent antioxidant activities have been efficiently and collectively synthesized. The synthetic approach features the following: (1) a stereoselective orthogonal one-pot glycosylation strategy for both 1,2-trans- and 1,2-cis-glycosidic linkages; (2) a merged reagent modulation and remote anchimeric assistance (RMRAA) α-glucosylation strategy; (3) DMF-modulated α-glucosylation; (4) convergent [3 + 4 + 6] orthogonal one-pot assembly of the target tridecasaccharide.
synthesis, glycan, glycosylation, Antioxidant activity, Cordyceps militaris
Structure type: oligomer ; 2210.7922 [M+H]+
C
83H
143NO
66H
Location inside paper: abstract, scheme 1(B), p. S36, structure 1
Aglycon: (CH2)5NH2
Trivial name: polysaccharide P70-1
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_142487,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153201,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_156493,IEDB_190606,IEDB_76933,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_198,SB_44,SB_6,SB_67,SB_7,SB_72,SB_88
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical synthesis, glycosylation, optical rotation measurement, orthogonal one-pot glycosylation
Synthetic data: chemical
Comments, role: A tridecasaccharide repeating unit 1
Related record ID(s): 51648
NCBI Taxonomy refs (TaxIDs): 73501
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1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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