Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2007-05-30 11:00:13 UTC |
---|
Update Date | 2021-09-14 15:39:07 UTC |
---|
HMDB ID | HMDB0006692 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Disialyllactose |
---|
Description | Disialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cell's surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287 , 16104015 , 7263800 , 7972078 ). |
---|
Structure | [H][C@]1(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@@H](CO)O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@H]2O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1 |
---|
Synonyms | Value | Source |
---|
a-Neu5ac-(2->8)-a-neu5ac-(2->3)-b-D-gal-(1->4)-D-GLC | HMDB | alpha-Neu5ac-(2->8)-alpha-neu5ac-(2->3)-beta-D-gal-(1->4)-D-GLC | HMDB | Di-(N-acetylneuramin)lactose | HMDB | O-(N-Acetyl-a-neuraminosyl)-(2->8)-O-(N-acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose | HMDB | O-(N-Acetyl-a-neuraminyl)-(2->8)-O-(N-acetyl-a-neuraminyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)- D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)- D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose | HMDB | O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-delta- glucopyranose | HMDB | Sia-(2-8)-sia-(2-3)gal-(1-4)GLC | HMDB | (2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | Generator, HMDB | Disialyl lactose | MeSH, HMDB | AlphaNeu5ac(2,8)alphaneu5ac(2,3)betadgal(1,4)DGLC | MeSH, HMDB |
| Show more...
---|
Chemical Formula | C34H56N2O27 |
---|
Average Molecular Weight | 924.8056 |
---|
Monoisotopic Molecular Weight | 924.307044596 |
---|
IUPAC Name | (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid |
---|
Traditional Name | (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid |
---|
CAS Registry Number | 18409-15-9 |
---|
SMILES | [H][C@]1(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@@H](CO)O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@H]2O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO |
---|
InChI Identifier | InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1 |
---|
InChI Key | IESOVNOGVZBLMG-MTEFBGAJSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | N-acylneuraminic acids |
---|
Alternative Parents | |
---|
Substituents | - Oligosaccharide
- N-acylneuraminic acid
- Neuraminic acid
- C-glucuronide
- C-glycosyl compound
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Dicarboxylic acid or derivatives
- Pyran
- Oxane
- Acetamide
- Carboxamide group
- Hemiacetal
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Organopnictogen compound
- Primary alcohol
- Carbonyl group
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
---|
Spectra |
---|
| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 10V, Positive-QTOF | splash10-0cel-0828015098-b2d713e51be84bbf8263 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 20V, Positive-QTOF | splash10-00mo-0209003000-1ce09f03167f95ceab80 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 40V, Positive-QTOF | splash10-03dl-6938001000-df20adf0314406572cbf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 10V, Negative-QTOF | splash10-0abc-2923810044-d28ff343a24de5edba71 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 20V, Negative-QTOF | splash10-0a70-8549110001-d97c4fa07291d27d2520 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 40V, Negative-QTOF | splash10-0a4i-3559000000-43c7b65e0c738d84bc62 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 10V, Positive-QTOF | splash10-05di-1311051209-8ba4b8dda3057cd245b8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 20V, Positive-QTOF | splash10-03l1-0491412612-76931820494134177702 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 40V, Positive-QTOF | splash10-00pi-9870313140-5d37d73734c32dc83273 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 10V, Negative-QTOF | splash10-00di-8090100084-7f9ba834399e650bd8eb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 20V, Negative-QTOF | splash10-001i-3090000020-6930c6437640788f5ca7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialyllactose 40V, Negative-QTOF | splash10-0006-9462010020-9d07f528035ec4ad7db1 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
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 |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | Not Available |
---|
Biospecimen Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB021805 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 10174971 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 12002504 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Stahl, Bernd; Boehm, Guenther; Finke, Berndt; Georgi, Gilda; Jelinek, Juergen; Schmitt, Joachim J. Oligosaccharide mixture. Ger. Offen. (2001), 6 pp. CODEN: GWXXBX DE 19958985 A1 20010613 CAN 135:18816 AN 2001:431764 |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - von Nicolai H, Esser P, Lauer E: Partial purification and properties of neuraminidase from Bifidobacterium lactentis. Hoppe Seylers Z Physiol Chem. 1981 Feb;362(2):153-62. [PubMed:7216169 ]
- Conway MC, Whittal RM, Baldwin MA, Burlingame AL, Balhorn R: Electrospray mass spectrometry of NeuAc oligomers associated with the C fragment of the tetanus toxin. J Am Soc Mass Spectrom. 2006 Jul;17(7):967-76. Epub 2006 May 19. [PubMed:16713287 ]
- Jayaraman S, Eswaramoorthy S, Kumaran D, Swaminathan S: Common binding site for disialyllactose and tri-peptide in C-fragment of tetanus neurotoxin. Proteins. 2005 Nov 1;61(2):288-95. [PubMed:16104015 ]
- Veh RW, Michalski JC, Corfield AP, Sander-Wewer M, Gies D, Schauer R: New chromatographic system for the rapid analysis and preparation of colostrum sialyloligosaccharides. J Chromatogr. 1981 Aug 7;212(3):313-22. [PubMed:7263800 ]
- Cho JW, Troy FA 2nd: Polysialic acid engineering: synthesis of polysialylated neoglycosphingolipids by using the polysialyltransferase from neuroinvasive Escherichia coli K1. Proc Natl Acad Sci U S A. 1994 Nov 22;91(24):11427-31. [PubMed:7972078 ]
|
---|