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Record Information
Version3.6
Creation Date2007-05-24 16:11:40 UTC
Update Date2013-05-29 19:44:29 UTC
HMDB IDHMDB06591
Secondary Accession NumbersNone
Metabolite Identification
Common NameLactosamine
DescriptionLactosamine is a disaccharide composed of galactose b1,4-linked to N-acetylglucosamine, and is a common constituent of complex N-linked glycans in metazoans. Unmodified terminal lactosamine, however, is less typical in tissues, since it is often further modified by additional substitutions, such as fucose, sialic acid, or sulfate to form a number of significant receptor and signaling molecules. Lactosamine-containing glycans are also required for proper targeting and maintenance of olfactory axons, and may also function in other sensory regions.(PMID: 17111357 ).
Structure
Thumb
Synonyms
  1. 2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose
  2. 2-Amino-2-deoxy-4-O-beta-delta-galactopyranosyl-delta-glucose
  3. beta-D-Galactopyranosyl-(1->4)-2-amino-2-deoxy-D-glucose
  4. beta-D-Galactopyranosyl-(1->4)-D-glucosamine
  5. beta-delta-Galactopyranosyl-(1->4)-2-amino-2-deoxy-delta-glucose
  6. beta-delta-Galactopyranosyl-(1->4)-delta-glucosamine
  7. LACN
  8. Polylactosamine
Chemical FormulaC12H23NO10
Average Molecular Weight341.3117
Monoisotopic Molecular Weight341.132195961
IUPAC Name(2R,3R,4S,5R)-2-amino-3,5,6-trihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal
Traditional IUPAC Namelactosamine
CAS Registry Number13000-25-4
SMILES
N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO
InChI Identifier
InChI=1S/C12H23NO10/c13-4(1-14)7(18)11(5(17)2-15)23-12-10(21)9(20)8(19)6(3-16)22-12/h1,4-12,15-21H,2-3,13H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1
InChI KeyLAVNEPYDFKGEOD-JVCRWLNRSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassTetrasaccharides
Sub ClassTetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Polyamine
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentTetrahexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
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 Solubility342 g/LALOGPS
logP-2.9ALOGPS
logP-5.4ChemAxon
logS0ALOGPS
pKa (Strongest Acidic)12.12ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area203.16ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity71.42ChemAxon
Polarizability31.56ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue LocationNot Available
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 IDFDB019859
KNApSAcK IDNot Available
Chemspider ID106391
KEGG Compound IDC00203
BioCyc IDBETA-D-GALACTOSYL-ETCETERA-GALACTOSAMINY
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06591
Metagene LinkHMDB06591
METLIN ID3675
PubChem Compound119065
PDB IDNot Available
ChEBI ID25001
References
Synthesis ReferencePark W K; Aravind S; Romanowska A; Renaud J; Roy R Syntheses of clustered lactosides by telomerization. Methods in enzymology (1994), 242 294-304.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Henion TR, Schwarting GA: Patterning the developing and regenerating olfactory system. J Cell Physiol. 2007 Feb;210(2):290-7. Pubmed: 17111357

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in the biosynthesis of gangliosides GM2, GD2 and GA2.
Gene Name:
B4GALNT1
Uniprot ID:
Q00973
Molecular weight:
58881.78
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has a highest activity toward Muc7, EA2 and Muc2, with a lowest activity than GALNT2. Glycosylates 'Thr-57' of SELPLG.
Gene Name:
GALNT4
Uniprot ID:
Q8N4A0
Molecular weight:
45701.465
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward HIV envelope glycoprotein gp120, EA2, Muc2 and Muc5. Probably glycosylates fibronectin in vivo. Glycosylates FGF23. Plays a central role in phosphate homeostasis.
Gene Name:
GALNT3
Uniprot ID:
Q14435
Molecular weight:
72609.79
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Probably catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNT8
Uniprot ID:
Q9NY28
Molecular weight:
72850.77
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Although it displays a much weaker activity toward all substrates tested compared to GALNT2, it is able to transfer up to seven GalNAc residues to the Muc5AC peptide, suggesting that it can fill vicinal Thr/Ser residues in cooperation with other GALNT proteins. Prefers Muc1a as substrate.
Gene Name:
GALNTL2
Uniprot ID:
Q8N3T1
Molecular weight:
73062.79
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
May catalyze the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNTL1
Uniprot ID:
Q8N428
Molecular weight:
63073.595
General function:
Involved in metal ion binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward Muc5Ac and EA2 peptide substrates.
Gene Name:
GALNT10
Uniprot ID:
Q86SR1
Molecular weight:
68991.22
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
May catalyze the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNTL4
Uniprot ID:
Q6P9A2
Molecular weight:
69559.95
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Glycopeptide transferase involved in O-linked oligosaccharide biosynthesis, which catalyzes the transfer of an N-acetyl-D-galactosamine residue to an already glycosylated peptide. In contrast to other proteins of the family, it does not act as a peptide transferase that transfers GalNAc onto serine or threonine residue on the protein receptor, but instead requires the prior addition of a GalNAc on a peptide before adding additional GalNAc moieties. Some peptide transferase activity is however not excluded, considering that its appropriate peptide substrate may remain unidentified
Gene Name:
GALNT7
Uniprot ID:
Q86SF2
Molecular weight:
75388.6
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. May participate in synthesis of oncofetal fibronectin. Has activity toward Muc1a, Muc2, EA2 and fibronectin peptides.
Gene Name:
GALNT6
Uniprot ID:
Q8NCL4
Molecular weight:
71158.055
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Displays activity toward mucin-derived peptide substrates such as Muc2, Muc5AC, Muc7, and Muc13 (-58). May be involved in O-glycosylation in kidney.
Gene Name:
GALNT14
Uniprot ID:
Q96FL9
Molecular weight:
64288.56
General function:
Involved in manganese ion binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has a broad spectrum of substrates for peptides such as EA2, Muc5AC, Muc1a, Muc1b. Probably involved in O-linked glycosylation of the immunoglobulin A1 (IgA1) hinge region.
Gene Name:
GALNT2
Uniprot ID:
Q10471
Molecular weight:
64732.35
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward non-glycosylated peptides such as Muc5AC, Muc1a and EA2, and no detectable activity with Muc2 and Muc7. Displays enzymatic activity toward the Gal-NAc-Muc5AC glycopeptide, but no detectable activity to mono-GalNAc-glycosylated Muc1a, Muc2, Muc7 and EA2. May play an important role in the initial step of mucin-type oligosaccharide biosynthesis in digestive organs.
Gene Name:
GALNT12
Uniprot ID:
Q8IXK2
Molecular weight:
66937.79
General function:
Involved in manganese ion binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has a broad spectrum of substrates for peptides such as EA2, Muc5AC, Muc1a, Muc1b and Muc7.
Gene Name:
GALNT1
Uniprot ID:
Q10472
Molecular weight:
64218.52
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward EA2 peptide substrate, but has a weak activity toward Muc2 or Muc1b substrates (By similarity).
Gene Name:
GALNT5
Uniprot ID:
Q7Z7M9
Molecular weight:
106265.345
General function:
Involved in galactosyltransferase activity
Specific function:
Transfers N-acetylgalactosamine onto globotriaosylceramide.
Gene Name:
B3GALNT1
Uniprot ID:
O75752
Molecular weight:
39511.55
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
This protein is the basis of the ABO blood group system. The histo-blood group ABO involves three carbohydrate antigens: A, B, and H. A, B, and AB individuals express a glycosyltransferase activity that converts the H antigen to the A antigen (by addition of UDP-GalNAc) or to the B antigen (by addition of UDP-Gal), whereas O individuals lack such activity.
Gene Name:
ABO
Uniprot ID:
P16442
Molecular weight:
40933.555
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Has both beta-1,3-glucuronic acid and beta-1,4-N-acetylgalactosamine transferase activity. Transfers glucuronic acid (GlcUA) from UDP-GlcUA and N-acetylgalactosamine (GalNAc) from UDP-GalNAc to the non-reducing end of the elongating chondroitin polymer. Specific activity is much reduced compared to CHSY1.
Gene Name:
CHSY3
Uniprot ID:
Q70JA7
Molecular weight:
100283.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Has both beta-1,3-glucuronic acid and beta-1,4-N-acetylgalactosamine transferase activity. Transfers glucuronic acid (GlcUA) from UDP-GlcUA and N-acetylgalactosamine (GalNAc) from UDP-GalNAc to the non-reducing end of the elongating chondroitin polymer.
Gene Name:
CHPF
Uniprot ID:
Q8IZ52
Molecular weight:
68367.94
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Has both beta-1,3-glucuronic acid and beta-1,4-N-acetylgalactosamine transferase activity. Transfers glucuronic acid (GlcUA) from UDP-GlcUA and N-acetylgalactosamine (GalNAc) from UDP-GalNAc to the non-reducing end of the elongating chondroitin polymer. Involved in the negative control of osteogenesis likely through the modulation of NOTCH signaling.
Gene Name:
CHSY1
Uniprot ID:
Q86X52
Molecular weight:
91783.785
General function:
Involved in binding
Specific function:
Catalyzes the transfer of a single N-acetylglucosamine from UDP-GlcNAc to a serine or threonine residue in cytoplasmic and nuclear proteins resulting in their modification with a beta-linked N-acetylglucosamine (O-GlcNAc). Glycosylates a large and diverse number of proteins including histone H2B, AKT1, PFKL, MLL5, MAPT/TAU and HCFC1. Can regulate their cellular processes via cross-talk between glycosylation and phosphorylation or by affecting proteolytic processing. Involved in insulin resistance in muscle and adipocyte cells via glycosylating insulin signaling components and inhibiting the 'Thr-308' phosphorylation of AKT1, enhancing IRS1 phosphorylation and attenuating insulin signaling. Involved in glycolysis regulation by mediating glycosylation of 6-phosphofructokinase PFKL, inhibiting its activity. Component of a THAP1/THAP3-HCFC1-OGT complex that is required for the regulation of the transcriptional activity of RRM1. As part of the NSL complex it may be involved in acetylation of nucleosomal histone H4 on several lysine residues. Isoform 2, the mitochondrial isoform (mOGT), is cytotoxic and triggers apoptosis in several cell types including INS1, an insulinoma cell line.
Gene Name:
OGT
Uniprot ID:
O15294
Molecular weight:
116923.515
General function:
Involved in sugar binding
Specific function:
Not Available
Gene Name:
GALNT13
Uniprot ID:
Q68VI8
Molecular weight:
64050.1
General function:
Involved in protein binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Does not glycosylate apomucin or SDC3.
Gene Name:
GALNT9
Uniprot ID:
Q9HCQ5
Molecular weight:
68388.61
General function:
Involved in metal ion binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNTL6
Uniprot ID:
Q49A17
Molecular weight:
69787.21
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
May catalyze the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D- galactosamine residue to a serine or threonine residue on the protein receptor
Gene Name:
GALNTL5
Uniprot ID:
Q7Z4T8
Molecular weight:
51480.1
General function:
Involved in sugar binding
Specific function:
Not Available
Gene Name:
GALNT20
Uniprot ID:
Q2L4S5
Molecular weight:
67750.5