1.0 2011-09-21 00:38:24 UTC 2015-07-21 06:57:58 UTC FDB024008 Difucosyllacto-N-hexaose b 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) [HMDB] Difucosyllacto-N-hexaose b C52H88N2O39 1365.2451 1364.496421084 N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-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}-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]ethanimidic acid N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-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}-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]ethanimidic acid 98359-76-3 [H][C@@](O)(CO)[C@@]([H])(O[C@]1([H])OC(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@]([H])(O[C@]3([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])NC(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@]3([H])O)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]2([H])NC(C)=O)[C@@]1([H])O)[C@]([H])(O)[C@@]([H])(O)C=O 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 BCENFJUGBDUPJS-JTGDLCLGSA-N 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. Oligosaccharides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Acetamides Alkyl glycosides Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Hydrocarbon derivatives N-acyl-alpha-hexosamines O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aldehyde Aliphatic heteromonocyclic compound Alkyl glycoside Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty acyl glycoside Glycosyl compound Hydrocarbon derivative N-acyl-alpha-hexosamine O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp -1.92 ALOGPS logs -0.73 ALOGPS solubility 2.57e+02 g/l ALOGPS logp -13 ChemAxon pka_strongest_acidic 5.15 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac N-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-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}-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]ethanimidic acid ChemAxon average_mass 1365.2451 ChemAxon mono_mass 1364.496421084 ChemAxon smiles [H][C@@](O)(CO)[C@@]([H])(O[C@]1([H])OC(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@]([H])(O[C@]3([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])NC(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@]3([H])O)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]2([H])NC(C)=O)[C@@]1([H])O)[C@]([H])(O)[C@@]([H])(O)C=O ChemAxon formula C52H88N2O39 ChemAxon inchi 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 ChemAxon inchikey BCENFJUGBDUPJS-JTGDLCLGSA-N ChemAxon polar_surface_area 656.53 ChemAxon refractivity 284.4 ChemAxon polarizability 129.64 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 41 ChemAxon donor_count 24 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06619 #<Reference:0x000055ce300b9f60> #<Reference:0x000055ce300b9da8> #<Reference:0x000055ce300b9bf0> #<Reference:0x000055ce300b9a38> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823