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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:44 UTC
HMDB IDHMDB01542
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyllactosamine
DescriptionN-Acetyllactosamine is an intermediate in the biosynthesis of Keratan sulfate and the biosynthesis of N-Glycan. It is a substrate for Beta-1,4-galactosyltransferase 4, Beta-1,4-galactosyltransferase 2, Beta-1,4-galactosyltransferase 1, Beta-1,4-galactosyltransferase 3 and CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,6-sialyltransferase.
Structure
Thumb
Synonyms
  1. beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamine
  2. beta-D-Galactosyl-1,4-N-acetyl-D-glucosamine
  3. beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamine
  4. beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamine
  5. D-Galactopyranosyl
  6. delta-Galactopyranosyl
  7. N-Acetyl-Lactosamine
  8. N-Acetyllactosamine
Chemical FormulaC14H25NO11
Average Molecular Weight383.3484
Monoisotopic Molecular Weight383.142760647
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-acetyllactosamine
CAS Registry Number32181-59-2
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
InChI Identifier
InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1
InChI KeyKFEUJDWYNGMDBV-LODBTCKLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassTetrasaccharides
Sub ClassTetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentTetrahexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Keratan sulfate biosynthesis
  • Component of N-Glycan biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility259.0ALOGPS
logP-2.8ALOGPS
logP-5ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area198.4 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.44 m3·mol-1ChemAxon
Polarizability35.67 Å3ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Epidermis
  • Intestine
  • Spleen
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB019860
KNApSAcK IDNot Available
Chemspider ID388404
KEGG Compound IDC00611
BioCyc IDBETA-D-GALACTOSYL-ETCETERA-GLUCO
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01542
Metagene LinkHMDB01542
METLIN ID4231
PubChem Compound439271
PDB IDNot Available
ChEBI ID16153
References
Synthesis ReferenceDekany, Gyula; Agoston, Karoly; Bajza, Istvan; Boejstrup, Marie; Kroeger, Lars. Process for the large-scale preparation of N-acetyllactosamine, lactosamine, lactosamine salts and lactosamine-containing oligosaccharides. PCT Int. Appl. (2007), 44pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jung SK, Fujimoto D: A novel beta-galactoside-binding lectin in adult rat kidney. J Biochem (Tokyo). 1994 Sep;116(3):547-53. Pubmed: 7852273
  2. Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. Pubmed: 1366057
  3. Yu LC, Twu YC, Chang CY, Lin M: Molecular basis of the adult i phenotype and the gene responsible for the expression of the human blood group I antigen. Blood. 2001 Dec 15;98(13):3840-5. Pubmed: 11739194
  4. Dabelsteen E, Buschard K, Hakomori S, Young WW: Pattern of distribution of blood group antigens on human epidermal cells during maturation. J Invest Dermatol. 1984 Jan;82(1):13-7. Pubmed: 6361167
  5. Ahmed H, Pohl J, Fink NE, Strobel F, Vasta GR: The primary structure and carbohydrate specificity of a beta-galactosyl-binding lectin from toad (Bufo arenarum Hensel) ovary reveal closer similarities to the mammalian galectin-1 than to the galectin from the clawed frog Xenopus laevis. J Biol Chem. 1996 Dec 20;271(51):33083-94. Pubmed: 8955156
  6. Hosomi O, Takeya A: The relationship between the (beta 1-3) N-acetylglucosaminyltransferase and the presence of oligosaccharides containing lacto-N-triose II structure in bovine and human milk. Nippon Juigaku Zasshi. 1989 Feb;51(1):1-6. Pubmed: 2522567
  7. Jinno K, Moriwaki S, Govindarajan S, Okada Y, Tsuji T: Blood group antigens in the intrahepatic biliary tree. II. Type 1 chain N-acetyllactosamine-related carbohydrate antigens in the proliferated bile ductules. J Hepatol. 1989 May;8(3):330-7. Pubmed: 2732447
  8. Takeya A, Hosomi O, Kogure T: The presence of N-acetyllactosamine and lactose: beta (1-3)N-acetylglucosaminyltransferase activity in human urine. Jpn J Med Sci Biol. 1985 Feb;38(1):1-8. Pubmed: 3160874
  9. Draberova L, Cerna H, Brodska H, Boubelik M, Watt SM, Stanners CP, Draber P: Soluble isoforms of CEACAM1 containing the A2 domain: increased serum levels in patients with obstructive jaundice and differences in 3-fucosyl-N-acetyl-lactosamine moiety. Immunology. 2000 Oct;101(2):279-87. Pubmed: 11012782
  10. Kojima S, Eguchi H, Ookawara T, Fujiwara N, Yasuda J, Nakagawa K, Yamamura T, Suzuki K: Clostridium botulinum type A progenitor toxin binds to Intestine-407 cells via N-acetyllactosamine moiety. Biochem Biophys Res Commun. 2005 Jun 3;331(2):571-6. Pubmed: 15850798
  11. Hosomi O, Takeya A, Kogure T: Human serum contains N-acetyllactosamine: beta 1-3 N-acetylglucosaminyltransferase activity. J Biochem (Tokyo). 1984 Jun;95(6):1655-9. Pubmed: 6236210
  12. Dabelsteen E, Holbrook K, Clausen H, Hakomori S: Cell surface carbohydrate changes during embryonic and fetal skin development. J Invest Dermatol. 1986 Jul;87(1):81-5. Pubmed: 3522754
  13. Argueso P, Spurr-Michaud S, Tisdale A, Gipson IK: Variation in the amount of T antigen and N-acetyllactosamine oligosaccharides in human cervical mucus secretions with the menstrual cycle. J Clin Endocrinol Metab. 2002 Dec;87(12):5641-8. Pubmed: 12466366

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues of keratan sulfate, another glycosaminoglycan, and the Gal residues in sialyl N-acetyllactosamine (sialyl LacNAc) oligosaccharides. May play a role in the maintenance of naive T-lymphocytes in the spleen.
Gene Name:
CHST3
Uniprot ID:
Q7LGC8
Molecular weight:
54705.5
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of galactose (Gal) residues of keratan. Has a preference for sulfating keratan sulfate, but it also transfers sulfate to the unsulfated polymer. The sulfotransferase activity on sialyl LacNAc structures is much higher than the corresponding desialylated substrate, and only internal Gal residues are sulfated. May function in the sulfation of sialyl N-acetyllactosamine oligosaccharide chains attached to glycoproteins. Participates in biosynthesis of selectin ligands. Selectin ligands are present in high endothelial cells (HEVs) and play a central role in lymphocyte homing at sites of inflammation.
Gene Name:
CHST1
Uniprot ID:
O43916
Molecular weight:
46714.21
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. Can produce lactose.
Gene Name:
B4GALT2
Uniprot ID:
O60909
Molecular weight:
41971.815
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. The cell surface form functions as a recognition molecule during a variety of cell to cell and cell to matrix interactions, as those occurring during development and egg fertilization, by binding to specific oligosaccharide ligands on opposing cells or in the extracellular matrix.
Gene Name:
B4GALT1
Uniprot ID:
P15291
Molecular weight:
43919.895
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of non-reducing N-acetylglucosamine (GlcNAc) residues. Preferentially acts on mannose-linked GlcNAc. Also able to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Also acts on core 2 mucin-type oligosaccharide and N-acetyllactosamine oligomer with a lower efficiency. Has weak or no activity toward keratan sulfate and oligosaccharides containing the Galbeta1-4GlcNAc. Catalyzes 6-O-sulfation of beta-benzyl GlcNAc but not alpha- or beta-benzyl GalNAc.
Gene Name:
CHST7
Uniprot ID:
Q9NS84
Molecular weight:
54265.635
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT3
Uniprot ID:
O60512
Molecular weight:
43927.63
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT4
Uniprot ID:
O60513
Molecular weight:
40040.865
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in binding
Specific function:
Plays an inhibitory role on natural killer (NK) cells cytotoxicity. Activation results in specific acid sphingomyelinase/SMPD1 stimulation with subsequent marked elevation of intracellular ceramide. Activation also leads to AKT1/PKB and RPS6KA1/RSK1 kinases stimulation as well as markedly enhanced T-cell proliferation induced by anti-CD3. Acts as a lectin that binds to the terminal carbohydrate Gal-alpha(1,3)Gal epitope as well as to the N-acetyllactosamine epitope. Binds also to CLEC2D/LLT1 as a ligand and inhibits NK cell-mediated cytotoxicity as well as interferon-gamma secretion in target cells
Gene Name:
KLRB1
Uniprot ID:
Q12918
Molecular weight:
25414.6