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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-24 10:24:09 UTC
Update Date2021-09-14 15:45:58 UTC
HMDB IDHMDB0006567
Secondary Accession Numbers
  • HMDB06567
Metabolite Identification
Common NameNeolactotetraose
DescriptionNeolactotetraose (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 ).
Structure
Data?1582752392
Synonyms
ValueSource
beta-D-Gal-(1->4)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-beta-D-GLCChEBI
beta-D-Galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucoseChEBI
BetaGal(1->4)betaglcnac(1->3)betagal(1->4)betaglcChEBI
Galb1-4glcnacb1-3galb1-4GLCBChEBI
Galbeta1-4glcnacbeta1-3galbeta1-4glcbetaChEBI
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-D1ChEBI
b-D-Gal-(1->4)-b-D-glcnac-(1->3)-b-D-gal-(1->4)-b-D-GLCGenerator
Β-D-gal-(1->4)-β-D-glcnac-(1->3)-β-D-gal-(1->4)-β-D-GLCGenerator
b-D-Galactosyl-(1->4)-N-acetyl-b-D-glucosaminyl-(1->3)-b-D-galactosyl-(1->4)-b-D-glucoseGenerator
Β-D-galactosyl-(1->4)-N-acetyl-β-D-glucosaminyl-(1->3)-β-D-galactosyl-(1->4)-β-D-glucoseGenerator
Gal(beta1->4)glcnac(beta1->3)gal(beta1->4)GLCHMDB
Gal(β1→4)glcnac(β1→3)gal(β1→4)GLCHMDB
Gal-glcnac-gal-GLCHMDB
Galp(beta1->4)glcpnac(beta1->3)galp(beta1->4)GLCPHMDB
Galp(β1→4)glcpnac(β1→3)galp(β1→4)GLCPHMDB
LNNTHMDB
Lacto-N-neotetraoseHMDB
N-NeotetraoseHMDB
O-beta-D-Galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-beta-D-Galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranoseHMDB
O-Β-D-galactopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-glucoseHMDB
O-Β-D-galactopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoseHMDB
beta-D-Gal-(1->4)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-D-GLCHMDB
beta-D-Galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucoseHMDB
beta-NeolactotetraoseHMDB
Β-D-gal-(1→4)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-D-GLCHMDB
Β-D-gal-(1→4)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-β-D-GLCHMDB
Β-D-galactosyl-(1→4)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-D-glucoseHMDB
Β-D-galactosyl-(1→4)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-β-D-glucoseHMDB
Β-neolactotetraoseHMDB
Galp-glcpnac-galp-GLCPHMDB
beta-D-Galactopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
beta-D-Galactopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranoseHMDB
beta-D-Galp-(1->4)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-D-GLCPHMDB
beta-D-Galp-(1->4)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-beta-D-GLCPHMDB
Β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-D-glucopyranoseHMDB
Β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoseHMDB
Β-D-galp-(1→4)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-D-GLCPHMDB
Β-D-galp-(1→4)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-β-D-GLCPHMDB
b-D-Galp-(1->4)-b-D-glcnacp-(1->3)-b-D-galp-(1->4)-b-D-GLCPGenerator
Β-D-galp-(1->4)-β-D-glcnacp-(1->3)-β-D-galp-(1->4)-β-D-GLCPGenerator
Chemical FormulaC26H45NO21
Average Molecular Weight707.632
Monoisotopic Molecular Weight707.248407473
IUPAC NameN-[(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
Traditional NameN-[(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
CAS Registry Number86594-19-6
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
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
InChI KeyIEQCXFNWPAHHQR-OEMKBTDYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:61844 )
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility145 g/LALOGPS
logP-2.6ALOGPS
logP-8.5ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)11.16ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area356.7 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity144.26 m³·mol⁻¹ChemAxon
Polarizability67.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+235.32130932474
DeepCCS[M-H]-233.59730932474
DeepCCS[M-2H]-267.62930932474
DeepCCS[M+Na]+241.50230932474
AllCCS[M+H]+245.232859911
AllCCS[M+H-H2O]+244.932859911
AllCCS[M+NH4]+245.532859911
AllCCS[M+Na]+245.532859911
AllCCS[M-H]-237.832859911
AllCCS[M+Na-2H]-239.732859911
AllCCS[M+HCOO]-241.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NeolactotetraoseCC(=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]1O4505.7Standard polar33892256
NeolactotetraoseCC(=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]1O5022.3Standard non polar33892256
NeolactotetraoseCC(=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]1O5751.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_1_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neolactotetraose GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 10V, Positive-QTOFsplash10-0a4l-0004034900-16054e9d7f89f9d981312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 20V, Positive-QTOFsplash10-054p-0204049300-1a81876938a3915e1a6b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 40V, Positive-QTOFsplash10-029t-9400136000-b29b059cf9da831bce482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 10V, Negative-QTOFsplash10-0a4j-1000009600-6aab2a0e0fbe18f02e3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 20V, Negative-QTOFsplash10-0bvi-6702019200-22402278dcf6155c35a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neolactotetraose 40V, Negative-QTOFsplash10-052f-9100132000-8f6ec29931c13ab9ba562021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified121 +/- 67.5 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified353.292(0-1172.93) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112368
KNApSAcK IDNot Available
Chemspider ID10279537
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21670519
PDB IDNot Available
ChEBI ID61844
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAly M R; Ibrahim el-S I; Ashry el-S H; Schmidt R R Synthesis of lacto-N-neotetraose and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group. Carbohydrate research (1999), 316(1-4), 121-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
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Enzymes

General function:
Involved in fucosyltransferase activity
Specific function:
Transfers a fucose to lacto-N-neotetraose but not to either alpha2,3-sialyl lacto-N-neotetraose or lacto-N-tetraose. Can catalyze the last step in the biosynthesis of Lewis antigen, the addition of a fucose to precursor polysaccharides
Gene Name:
FUT9
Uniprot ID:
Q9Y231
Molecular weight:
42040.7