Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-05-24 10:24:09 UTC |
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Update Date | 2021-09-14 15:45:58 UTC |
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HMDB ID | HMDB0006567 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Neolactotetraose |
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Description | Neolactotetraose (CAS: 13007-32-4), also known as lacto-N-neotetraose (LNnt), is a common oligosaccharide present in human breast milk. After lactose and lipids, human milk oligosaccharides (HMOs) are quantitatively the third largest and most diverse component of breast milk. These small mass HMOs are selectively metabolized by select bifidobacterial strains and represent a potential new class of bioactive molecules functioning as prebiotics to facilitate protective gut colonization in breast-fed newborns. The oligosaccharide composition of human milk varies among individuals. The geographical origin of the donors is one of the factors that account for this variability. This can be explained by genetically determined traits that are not uniformly distributed (PMID: 10420591 , 10697138 , 1370278 , 14533820 , 16239538 , 16441441 , 17101655 , 17372007 , 1910009 , 2452383 , 2474254 , 2988366 , 3926023 , 6083447 , 6798116 , 6874813 , 8193150 , 8416736 , 9353017 ). |
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Structure | CC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@@H]1O InChI=1S/C26H45NO21/c1-6(32)27-11-14(35)20(46-25-18(39)15(36)12(33)7(2-28)43-25)10(5-31)45-24(11)48-22-13(34)8(3-29)44-26(19(22)40)47-21-9(4-30)42-23(41)17(38)16(21)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32)/t7-,8-,9-,10-,11-,12+,13+,14-,15+,16-,17-,18-,19-,20-,21-,22+,23-,24+,25+,26+/m1/s1 |
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Synonyms | Value | Source |
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beta-D-Gal-(1->4)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-beta-D-GLC | ChEBI | beta-D-Galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose | ChEBI | BetaGal(1->4)betaglcnac(1->3)betagal(1->4)betaglc | ChEBI | Galb1-4glcnacb1-3galb1-4GLCB | ChEBI | Galbeta1-4glcnacbeta1-3galbeta1-4glcbeta | ChEBI | WURCS=2.0/3,4,3/[a2122h-1b_1-5][a2112h-1b_1-5][a2122h-1b_1-5_2*ncc/3=o]/1-2-3-2/a4-b1_b3-c1_c4-D1 | ChEBI | b-D-Gal-(1->4)-b-D-glcnac-(1->3)-b-D-gal-(1->4)-b-D-GLC | Generator | Β-D-gal-(1->4)-β-D-glcnac-(1->3)-β-D-gal-(1->4)-β-D-GLC | Generator | b-D-Galactosyl-(1->4)-N-acetyl-b-D-glucosaminyl-(1->3)-b-D-galactosyl-(1->4)-b-D-glucose | Generator | Β-D-galactosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->3)-β-D-galactosyl-(1->4)-β-D-glucose | Generator | Gal(beta1->4)glcnac(beta1->3)gal(beta1->4)GLC | HMDB | Gal(β1→4)glcnac(β1→3)gal(β1→4)GLC | HMDB | Gal-glcnac-gal-GLC | HMDB | Galp(beta1->4)glcpnac(beta1->3)galp(beta1->4)GLCP | HMDB | Galp(β1→4)glcpnac(β1→3)galp(β1→4)GLCP | HMDB | LNNT | HMDB | Lacto-N-neotetraose | HMDB | N-Neotetraose | HMDB | O-beta-D-Galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucose | HMDB | O-beta-D-Galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose | HMDB | O-Β-D-galactopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-glucose | HMDB | O-Β-D-galactopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose | HMDB | beta-D-Gal-(1->4)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-D-GLC | HMDB | beta-D-Galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucose | HMDB | beta-Neolactotetraose | HMDB | Β-D-gal-(1→4)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-D-GLC | HMDB | Β-D-gal-(1→4)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-β-D-GLC | HMDB | Β-D-galactosyl-(1→4)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-D-glucose | HMDB | Β-D-galactosyl-(1→4)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-β-D-glucose | HMDB | Β-neolactotetraose | HMDB | Galp-glcpnac-galp-GLCP | HMDB | beta-D-Galactopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-D-glucopyranose | HMDB | beta-D-Galactopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose | HMDB | beta-D-Galp-(1->4)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-D-GLCP | HMDB | beta-D-Galp-(1->4)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-beta-D-GLCP | HMDB | Β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-D-glucopyranose | HMDB | Β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose | HMDB | Β-D-galp-(1→4)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-D-GLCP | HMDB | Β-D-galp-(1→4)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-β-D-GLCP | HMDB | b-D-Galp-(1->4)-b-D-glcnacp-(1->3)-b-D-galp-(1->4)-b-D-GLCP | Generator | Β-D-galp-(1->4)-β-D-glcnacp-(1->3)-β-D-galp-(1->4)-β-D-GLCP | Generator |
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Chemical Formula | C26H45NO21 |
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Average Molecular Weight | 707.632 |
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Monoisotopic Molecular Weight | 707.248407473 |
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IUPAC Name | N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide |
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Traditional Name | N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide |
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CAS Registry Number | 86594-19-6 |
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SMILES | CC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@@H]1O |
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InChI Identifier | InChI=1S/C26H45NO21/c1-6(32)27-11-14(35)20(46-25-18(39)15(36)12(33)7(2-28)43-25)10(5-31)45-24(11)48-22-13(34)8(3-29)44-26(19(22)40)47-21-9(4-30)42-23(41)17(38)16(21)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32)/t7-,8-,9-,10-,11-,12+,13+,14-,15+,16-,17-,18-,19-,20-,21-,22+,23-,24+,25+,26+/m1/s1 |
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InChI Key | IEQCXFNWPAHHQR-OEMKBTDYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Oligosaccharides |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- N-acyl-alpha-hexosamine
- Glycosyl compound
- O-glycosyl compound
- Oxane
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Polyol
- Organopnictogen compound
- Primary alcohol
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Organonitrogen compound
- Carbonyl group
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | - beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:61844 )
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_12) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_13) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_14) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 10V, Positive-QTOF | splash10-0a4l-0004034900-16054e9d7f89f9d98131 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 20V, Positive-QTOF | splash10-054p-0204049300-1a81876938a3915e1a6b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 40V, Positive-QTOF | splash10-029t-9400136000-b29b059cf9da831bce48 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 10V, Negative-QTOF | splash10-0a4j-1000009600-6aab2a0e0fbe18f02e3b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 20V, Negative-QTOF | splash10-0bvi-6702019200-22402278dcf6155c35a8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neolactotetraose 40V, Negative-QTOF | splash10-052f-9100132000-8f6ec29931c13ab9ba56 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Aly MR, Ibrahim el-S I, Ashry el-S H, Schmidt RR: Synthesis of lacto-N-neotetraose and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group. Carbohydr Res. 1999 Mar 31;316(1-4):121-32. [PubMed:10420591 ]
- Bush CA, Panitch MM, Dua VK, Rohr TE: Carbon nuclear magnetic resonance spectra of oligosaccharides isolated from human milk and ovarian cyst mucin. Anal Biochem. 1985 Feb 15;145(1):124-36. [PubMed:2988366 ]
- Erney RM, Malone WT, Skelding MB, Marcon AA, Kleman-Leyer KM, O'Ryan ML, Ruiz-Palacios G, Hilty MD, Pickering LK, Prieto PA: Variability of human milk neutral oligosaccharides in a diverse population. J Pediatr Gastroenterol Nutr. 2000 Feb;30(2):181-92. [PubMed:10697138 ]
- Hengge UR, Kirschfink M, Konig AL, Nicklas W, Roelcke D: Characterization of I/F1 glycoprotein as a receptor for Mycoplasma pneumoniae. Infect Immun. 1992 Jan;60(1):79-83. [PubMed:1370278 ]
- Tsai CM: Molecular mimicry of host structures by lipooligosaccharides of Neisseria meningitidis: characterization of sialylated and nonsialylated lacto-N-neotetraose (Galbeta1-4GlcNAcbeta1-3Galbeta1-4Glc) structures in lipooligosaccharides using monoclonal antibodies and specific lectins. Adv Exp Med Biol. 2001;491:525-42. doi: 10.1007/978-1-4615-1267-7_35. [PubMed:14533820 ]
- Gulati S, Cox A, Lewis LA, Michael FS, Li J, Boden R, Ram S, Rice PA: Enhanced factor H binding to sialylated Gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in Gonococci. Infect Immun. 2005 Nov;73(11):7390-7. doi: 10.1128/IAI.73.11.7390-7397.2005. [PubMed:16239538 ]
- Steeghs L, van Vliet SJ, Uronen-Hansson H, van Mourik A, Engering A, Sanchez-Hernandez M, Klein N, Callard R, van Putten JP, van der Ley P, van Kooyk Y, van de Winkel JG: Neisseria meningitidis expressing lgtB lipopolysaccharide targets DC-SIGN and modulates dendritic cell function. Cell Microbiol. 2006 Feb;8(2):316-25. doi: 10.1111/j.1462-5822.2005.00623.x. [PubMed:16441441 ]
- Estabrook MM, Jarvis GA, McLeod Griffiss J: Affinity-purified human immunoglobulin G that binds a lacto-N-neotetraose-dependent lipooligosaccharide structure is bactericidal for serogroup B Neisseria meningitidis. Infect Immun. 2007 Feb;75(2):1025-33. doi: 10.1128/IAI.00882-06. Epub 2006 Nov 13. [PubMed:17101655 ]
- Madico G, Ngampasutadol J, Gulati S, Vogel U, Rice PA, Ram S: Factor H binding and function in sialylated pathogenic neisseriae is influenced by gonococcal, but not meningococcal, porin. J Immunol. 2007 Apr 1;178(7):4489-97. doi: 10.4049/jimmunol.178.7.4489. [PubMed:17372007 ]
- Tsai CM, Civin CI: Eight lipooligosaccharides of Neisseria meningitidis react with a monoclonal antibody which binds lacto-N-neotetraose (Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4Glc). Infect Immun. 1991 Oct;59(10):3604-9. [PubMed:1910009 ]
- Latov N, Hays AP, Donofrio PD, Liao J, Ito H, McGinnis S, Konstadoulakis M, Freddo L, Shy ME, et al.: Monoclonal IgM with unique specificity to gangliosides GM1 and GD1b and to lacto-N-tetraose associated with human motor neuron disease. Neurology. 1988 May;38(5):763-8. doi: 10.1212/wnl.38.5.763. [PubMed:2452383 ]
- Gooi HC, Veyrieres A, Alais J, Scudder P, Hounsell EF, Feizi T: Further studies of the specificities of monoclonal anti-i and anti-I antibodies using chemically synthesized, linear oligosaccharides of the poly-N-acetyllactosamine series. Mol Immunol. 1984 Nov;21(11):1099-104. [PubMed:6083447 ]
- Cheetham NW, Dube VE: Preparation of lacto-N-neotetraose from human milk by high-performance liquid chromatography. J Chromatogr. 1983 Jun 24;262:426-30. [PubMed:6874813 ]
- Wikstrand CJ, Longee DC, McLendon RE, Fuller GN, Friedman HS, Fredman P, Svennerholm L, Bigner DD: Lactotetraose series ganglioside 3',6'-isoLD1 in tumors of central nervous and other systems in vitro and in vivo. Cancer Res. 1993 Jan 1;53(1):120-6. [PubMed:8416736 ]
- Garin-Chesa P, Rettig WJ: Immunohistochemical analysis of LNT, NeuAc2----3LNT, and Lex carbohydrate antigens in human tumors and normal tissues. Am J Pathol. 1989 Jun;134(6):1315-27. [PubMed:2474254 ]
- Spitalnik SL, Schwartz JF, Magnani JL, Roberts DD, Spitalnik PF, Civin CI, Ginsburg V: Anti-My-28, an antigranulocyte mouse monoclonal antibody, binds to a sugar sequence in lacto-N-neotetraose. Blood. 1985 Aug;66(2):319-26. [PubMed:3926023 ]
- Kabat EA, Liao J, Shyong J, Osserman EF: A monoclonal IgM lambda macroglobulin with specificity for lacto-N-tetraose in a patient with bronchogenic carcinoma. J Immunol. 1982 Feb;128(2):540-4. [PubMed:6798116 ]
- Feizi T, Solomon JC, Yuen CT, Jeng KC, Frigeri LG, Hsu DK, Liu FT: The adhesive specificity of the soluble human lectin, IgE-binding protein, toward lipid-linked oligosaccharides. Presence of the blood group A, B, B-like, and H monosaccharides confers a binding activity to tetrasaccharide (lacto-N-tetraose and lacto-N-neotetraose) backbones. Biochemistry. 1994 May 24;33(20):6342-9. doi: 10.1021/bi00186a038. [PubMed:8193150 ]
- Estabrook MM, Griffiss JM, Jarvis GA: Sialylation of Neisseria meningitidis lipooligosaccharide inhibits serum bactericidal activity by masking lacto-N-neotetraose. Infect Immun. 1997 Nov;65(11):4436-44. [PubMed:9353017 ]
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