Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-25 14:51:04 UTC |
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Update Date | 2021-09-14 15:18:58 UTC |
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HMDB ID | HMDB0006619 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Difucosyllacto-N-hexaose b |
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Description | Difucosyllacto-N-hexaose b is a fucosyl-oligosaccharide from human breast milk. For several years biochemical studies on the carbohydrate composition of human milk have concerned only the dosage of lactose. In fact, even though oligosaccharides had already been identified at the end of the 19th century, the methods available at that time did not allow further data to be obtained on their precise amounts. The availability of more advanced techniques has recently made it possible to establish the precise amount of oligosaccharides in human milk during the different phases of lactation. The results obtained so far have quantified the concentration of such substances at 20 to 23 g l-1 in colostrum and 12 to 14 g l-1 in mature milk; thus, from the quantitative point of view, oligosaccharides represent the third component of human milk, following lactose and lipids. However, even though improvements have been made regarding the total amount of oligosaccharides, knowledge on the amount of each oligosaccharide in human milk remains inadequate. From the biochemical point of view, such substances result from the sequential addition of monosaccharides to the molecule of lactose, by specific glycosyltransferases of the mammary gland. In particular, monosaccharidic units represented by fucose (Fuc), galactose (Gal), N-acetylglucosamine (GlcNac) and sialic acid (NANA) are added to lactose, forming oligosaccharides of different dimensions, with a linear or ramified molecular structure. Such a synthetic process leads to the formation of a significant number of oligosaccharides. More than 80 oligosaccharides have already been identified which, on the basis of their chemical composition, can be classified as follows: (i) "core" oligosaccharides, made up of Glc, Gal and GlcNac, representing the starting structures for the synthesis of more complex oligosaccharides; (ii) fucosyl-oligosaccharides, deriving from the addition to the core of one or more molecules of Fuc; (iii) sialyloligosaccharides, resulting from the addition to the core of one or more molecules of NANA; and (iv) sialylfucosyl-oligosaccharides, containing both Fuc and NANA. The presence and the quantity of different types of oligosaccharides in human milk are genetically determined and closely related to the secretor state A, B, H and Lewis, with significant differences among the different genotypes. The most common phenotype, present in 70% of the general population, is represented by subjects expressing both the secretor and Lewis gene. The milk produced by these mothers is the richest in oligosaccharides. It is evidently difficult to analyse oligosaccharides of human milk as they are numerous and have a particularly complex structure. The data available until now demonstrate that the majority of human milk oligosaccharides is made up of molecules with three to nine monosaccharidic units (trisaccharides to nonasaccharides). (PMID:10569230 ). |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](OC3[C@@H](O)C(CO[C@@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H](O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]5O)[C@H]4NC(C)=O)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C52H88N2O39/c1-12-25(65)31(71)35(75)48(81-12)89-42-21(10-60)86-47(24(54-15(4)62)44(42)92-51-38(78)34(74)29(69)19(8-58)84-51)93-45-30(70)22(87-52(39(45)79)88-40(17(64)6-56)27(67)16(63)5-55)11-80-46-23(53-14(3)61)43(91-49-36(76)32(72)26(66)13(2)82-49)41(20(9-59)85-46)90-50-37(77)33(73)28(68)18(7-57)83-50/h5,12-13,16-52,56-60,63-79H,6-11H2,1-4H3,(H,53,61)(H,54,62)/t12-,13-,16-,17+,18+,19+,20+,21+,22?,23+,24+,25+,26+,27+,28-,29-,30-,31+,32+,33-,34-,35-,36-,37+,38+,39+,40+,41+,42+,43+,44+,45?,46+,47-,48-,49-,50+,51-,52-/m0/s1 |
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Synonyms | Value | Source |
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O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)]-O-beta-D-galactopyranosyl-(1->4)- D-glucose | HMDB | O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)]-O-beta-delta-galactopyranosyl-(1->4)- D-glucose | HMDB | N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidate | HMDB |
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Chemical Formula | C52H88N2O39 |
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Average Molecular Weight | 1365.2451 |
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Monoisotopic Molecular Weight | 1364.496421084 |
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IUPAC Name | N-[(2S,3R,4R,5S,6R)-2-{[(3S,5R,6S)-2-({[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide |
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Traditional Name | N-[(2S,3R,4R,5S,6R)-2-{[(3S,5R,6S)-2-({[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide |
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CAS Registry Number | 98359-76-3 |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](OC3[C@@H](O)C(CO[C@@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H](O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]5O)[C@H]4NC(C)=O)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O[C@@H]2O[C@H](CO)[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/C52H88N2O39/c1-12-25(65)31(71)35(75)48(81-12)89-42-21(10-60)86-47(24(54-15(4)62)44(42)92-51-38(78)34(74)29(69)19(8-58)84-51)93-45-30(70)22(87-52(39(45)79)88-40(17(64)6-56)27(67)16(63)5-55)11-80-46-23(53-14(3)61)43(91-49-36(76)32(72)26(66)13(2)82-49)41(20(9-59)85-46)90-50-37(77)33(73)28(68)18(7-57)83-50/h5,12-13,16-52,56-60,63-79H,6-11H2,1-4H3,(H,53,61)(H,54,62)/t12-,13-,16-,17+,18+,19+,20+,21+,22?,23+,24+,25+,26+,27+,28-,29-,30-,31+,32+,33-,34-,35-,36-,37+,38+,39+,40+,41+,42+,43+,44+,45?,46+,47-,48-,49-,50+,51-,52-/m0/s1 |
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InChI Key | BCENFJUGBDUPJS-ZVOZPCDCSA-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
- Fatty acyl glycoside
- N-acyl-alpha-hexosamine
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Beta-hydroxy aldehyde
- Fatty acyl
- Oxane
- Acetamide
- Alpha-hydroxyaldehyde
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Aldehyde
- Primary alcohol
- Organic nitrogen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 | | Show more...
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Predicted Chromatographic Properties | Predicted Kovats Retention IndicesNot Available |
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 10V, Positive-QTOF | splash10-0f72-5879000000-8c6655645d06a5b7ea79 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 20V, Positive-QTOF | splash10-0pbi-9643001010-425099fb137d0ee57f61 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 40V, Positive-QTOF | splash10-0a4s-9423000000-4dcfedef179c20dcaed3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 10V, Negative-QTOF | splash10-0fg2-6449200050-3652ce31142dcff6d1ba | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 20V, Negative-QTOF | splash10-0f92-2539011333-79263915d37e5794ba0f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 40V, Negative-QTOF | splash10-08p0-2410090712-ee226fedd0b0b3346845 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 10V, Negative-QTOF | splash10-03di-2339000000-e87d66353d6184eb03c0 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 20V, Negative-QTOF | splash10-08ms-5889000100-3eacb265b99337e0d7f9 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 40V, Negative-QTOF | splash10-0fbl-7921000000-15072920fcc017d993ca | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 10V, Positive-QTOF | splash10-0udr-7974000000-983c18aabc6c90a3edee | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 20V, Positive-QTOF | splash10-0kus-6935000000-2d03f67647bd4c1735aa | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Difucosyllacto-N-hexaose b 40V, Positive-QTOF | splash10-0603-9422004000-5acd94851602a14ac027 | 2021-09-25 | 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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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB024008 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 59651617 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53477876 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Dua, Virendra K.; Goso, Kazue; Dube, Volker E.; Bush, C. Allen. Characterization of lacto-N-hexaose and two fucosylated derivatives from human milk by high-performance liquid chromatography and proton NMR spectroscopy. Journal of Chromatography (1985), 328 259-69. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Dua VK, Goso K, Dube VE, Bush CA: Characterization of lacto-N-hexaose and two fucosylated derivatives from human milk by high-performance liquid chromatography and proton NMR spectroscopy. J Chromatogr. 1985 Jun 28;328:259-69. [PubMed:3839799 ]
- Yu H, Sipes JM, Cashel J, Bakos MA, Goldblum RM, Roberts DD: Recognition of type 1 chain oligosaccharides and lacto-series glycolipids by an antibody to human secretory component. Arch Biochem Biophys. 1995 Oct 1;322(2):299-305. [PubMed:7574700 ]
- Kunz C, Rudloff S, Hintelmann A, Pohlentz G, Egge H: High-pH anion-exchange chromatography with pulsed amperometric detection and molar response factors of human milk oligosaccharides. J Chromatogr B Biomed Appl. 1996 Oct 25;685(2):211-21. [PubMed:8953162 ]
- Coppa GV, Pierani P, Zampini L, Carloni I, Carlucci A, Gabrielli O: Oligosaccharides in human milk during different phases of lactation. Acta Paediatr Suppl. 1999 Aug;88(430):89-94. [PubMed:10569230 ]
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