Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:38:10 UTC |
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Updated at | 2021-08-12 19:51:53 UTC |
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NP-MRD ID | NP0002696 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | beta-gentiobiose |
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Provided By | BMRB |
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Description | Beta-D-Glcp-(1->6)-beta-D-Glcp is also known as b-D-GLC-(1->6)-b-D-GLC or beta-gentiobiose. beta-gentiobiose is found in Gentiana andrewsii, Gentiana macrophylla and Gentianopsis grandis. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on beta-D-Glcp-(1->6)-beta-D-Glcp (PMID: 19443021) (PMID: 25568069) (PMID: 31537530) (PMID: 34606556) (PMID: 34597702). |
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Structure | OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 |
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Synonyms | Value | Source |
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6-O-beta-D-Glucopyranosyl-beta-D-glucopyranose | ChEBI | beta-D-GLC-(1->6)-beta-D-GLC | ChEBI | beta-D-Glucosyl-(1->6)-beta-D-glucose | ChEBI | beta-Gentiobiose | ChEBI | GLCB1-6GLCB | ChEBI | Glcbeta1-6glcbeta | ChEBI | 6-O-b-D-Glucopyranosyl-b-D-glucopyranose | Generator | 6-O-Β-D-glucopyranosyl-β-D-glucopyranose | Generator | b-D-GLC-(1->6)-b-D-GLC | Generator | Β-D-GLC-(1->6)-β-D-GLC | Generator | b-D-Glucosyl-(1->6)-b-D-glucose | Generator | Β-D-glucosyl-(1->6)-β-D-glucose | Generator | b-Gentiobiose | Generator | Β-gentiobiose | Generator | b-D-GLCP-(1->6)-b-D-GLCP | Generator | Β-D-GLCP-(1->6)-β-D-GLCP | Generator | Amygdalose | PhytoBank, MeSH | D-Gentiobiose | PhytoBank, MeSH | 6-O-beta-D-Glucopyranosyl-D-glucose | PhytoBank | 6-O-β-D-Glucopyranosyl-D-glucose | PhytoBank | 6-(beta-D-Glucosido)-D-glucose | PhytoBank | 6-(β-D-Glucosido)-D-glucose | PhytoBank | 6-O-beta-D-glucopyranosyl-D-glucopyranose | PhytoBank | 6-O-β-D-glucopyranosyl-D-glucopyranose | PhytoBank | beta-D-Glc-(1->6)-D-Glc | PhytoBank | β-D-Glc-(1→6)-D-Glc | PhytoBank | beta-D-Glcp-(1->6)-D-Glcp | PhytoBank | β-D-Glcp-(1→6)-D-Glcp | PhytoBank | beta-D-glucopyranosyl-(1->6)-D-glucose | PhytoBank | β-D-glucopyranosyl-(1→6)-D-glucose | PhytoBank | beta-D-glucosyl-(1->6)-D-glucose | PhytoBank | β-D-glucosyl-(1→6)-D-glucose | PhytoBank | D-Glc(beta1->6)D-Glc | PhytoBank | D-Glc(β1→6)D-Glc | PhytoBank | beta-D-Glc-(1→6)-D-Glc | PhytoBank | beta-D-Glcp-(1→6)-D-Glcp | PhytoBank | beta-D-glucopyranosyl-(1→6)-D-glucose | PhytoBank | beta-D-glucosyl-(1→6)-D-glucose | PhytoBank | D-Glc(beta1→6)D-Glc | PhytoBank |
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Chemical Formula | C12H22O11 |
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Average Mass | 342.2970 Da |
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Monoisotopic Mass | 342.11621 Da |
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IUPAC Name | (2R,3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol |
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Traditional Name | gentiobiose |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 |
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InChI Key | DLRVVLDZNNYCBX-LIZSDCNHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Classification | Not classified |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS: Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. J Allergy Clin Immunol. 2009 Jun;123(6):1268-76.e15. doi: 10.1016/j.jaci.2009.03.013. Epub 2009 May 13. [PubMed:19443021 ]
- Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S: The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Sci Transl Med. 2015 Jan 7;7(269):269ra1. doi: 10.1126/scitranslmed.3010524. [PubMed:25568069 ]
- Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S: The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies. Blood. 2019 Nov 28;134(22):1941-1950. doi: 10.1182/blood.2019001705. [PubMed:31537530 ]
- Li J, Wu H, Liu Y, Nan J, Park HJ, Chen Y, Yang L: The chemical structure and immunomodulatory activity of an exopolysaccharide produced by Morchella esculenta under submerged fermentation. Food Funct. 2021 Oct 4;12(19):9327-9338. doi: 10.1039/d1fo01683k. [PubMed:34606556 ]
- Feng X, Du C, Wang C: Structural characterization of polysaccharide from yellow sweet potato and ameliorates DSS-induced mice colitis by active GPR41/MEK/ERK 1/2 signaling pathway. Int J Biol Macromol. 2021 Sep 28. pii: S0141-8130(21)02103-6. doi: 10.1016/j.ijbiomac.2021.09.175. [PubMed:34597702 ]
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