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Showing metabocard for Difucosyllacto-N-hexaose b (HMDB06619)

Record Information
Version 3.5
Creation Date 2007-05-25 08:51:04 -0600
Update Date 2013-02-08 17:15:06 -0700
HMDB ID HMDB06619
Secondary Accession Numbers None
Metabolite Identification
Common Name Difucosyllacto-N-hexaose b
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 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. Difucosyllacto-N-hexaose b
  2. 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
  3. 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
Chemical Formula C52H88N2O39
Average Molecular Weight 1365.2451
Monoisotopic Molecular Weight 1364.496421084
IUPAC Name N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-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}-3,5-dihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)-5-{[(2S,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]acetamide
Traditional IUPAC Name N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-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}-3,5-dihydroxy-6-{[(2R,3R
CAS Registry Number 98359-76-3
SMILES [H][C@@](O[C@@H]1OC(CO[C@@H]2O[C@H](CO)[C@@H](O[C@]3([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H](O[C@]3([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]3O)[C@H]2NC(C)=O)[C@H](O)C(O[C@]2([H])O[C@H](CO)[C@@H](O[C@]3([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]3O)[C@H](O[C@]3([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H]2NC(C)=O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O
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
InChI Key BCENFJUGBDUPJS-JTGDLCLGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Oligosaccharides
Sub Class Hexose Oligosaccharides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Hexose Oligosaccharides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental 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
Predicted Properties
Property Value Source
Water Solubility 146 g/L ALOGPS
LogP -1.76 ALOGPS
LogP -14 ChemAxon
LogS -0.97 ALOGPS
pKa (strongest acidic) 11.29 ChemAxon
pKa (strongest basic) -3.9 ChemAxon
Hydrogen Acceptor Count 39 ChemAxon
Hydrogen Donor Count 24 ChemAxon
Polar Surface Area 649.55 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 283.35 ChemAxon
Polarizability 129.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024008
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06619 Link_out
Metagene Link HMDB06619 Link_out
METLIN ID Not Available
PubChem Compound 53477876 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
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.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out