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PubMed2001

Rapid and simple preparation of N-linked oligosaccharides by cellulose-column chromatography.

As a means of preparing N-linked oligosaccharides from hydrazinolysates of glycoproteins in a rapid and simple manner, a method has been developed using cellulose-column chromatography. Hydrazinolysates of human IgG, containing a series of biantennary complex type oligosaccharides, were applied to a cellulose column equilibrated with (4:1:1, v/v) 1-butanol-ethanol-water. The N-linked oligosaccharides were eluted with (1:1, v/v) ethanol-water, and analyzed by HPLC in combination with sequential glycosidase digestion. The oligosaccharides, with or without sialic acid, were quantitatively recovered in the fraction eluted with (1:1, v/v) ethanol-water without UV-detectable contamination by impurities derived from protein or the cellulose. Other types of N-linked oligosaccharides of alpha1-acid glycoprotein (tetraantennary complex-type), ovalbumin (hybrid-type), and ribonuclease B (high mannose-type) were also quantitatively prepared from the hydrazinolysates by elution of the cellulose column with (1:1, v/v) ethanol-water and these had as high a quality as those prepared by conventional paper chromatography.

Animals↗

PubMed1997

1H NMR analysis of novel sialylated and fucosylated lactose-based oligosaccharides having linear GlcNAc(beta 1-6) Gal and Neu5Ac(alpha 2-6) GlcNAc sequences.

Three novel oligosaccharides of human infant faeces have been fully characterised by methylation analysis and 500/600 MHz 1H NMR spectroscopy including DQF-COSY, TQF-COSY, TOCSY and ROESY experiments. The oligosaccharides were shown to be lactose-based structures two of which were substituted at C-6 of Gal with either the Le(x) trisaccharide, Gal(beta 1-4)[Fuc(alpha 1-3)]GlcNAc(beta 1-, or Neu5Ac(alpha 2-6)Gal(beta 1-4)GlcNAc(beta 1-. They differ from other free oligosaccharides previously isolated from the human by having the (1-->6) linkage to Gal in the absence of a (1-->3) branch. The third oligosaccharide has Neu5Ac(alpha 2-6) linked to GlcNAc of the trisaccharide GlcNAc(beta 1-3)Gal(beta 1-4)Glc. This is a linear fragment of the disialylated tetrasaccharide sequence Neu5Ac(alpha 2-3)Gal(beta 1-3)[Neu5Ac(alpha 2-6)]GlcNAc(beta 1-found in the milk oligosaccharide disialyl LNT (the GlcNAc residue of the tetrasaccharide linked to lactose) and also of N-linked chains (GlcNAc linked to Man).

Breast Feeding↗

PubMed1997

Oligosaccharides obtained by enzymatic hydrolysis of birch kraft pulp xylan: analysis by capillary zone electrophoresis and mass spectrometry.

Neutral and acidic oligosaccharides were obtained from an unbleached birch kraft pulp by treatment with a Trichoderma reesei endoxylanase pI 9 and subsequently characterized using capillary zone electrophoresis (CZE) and matrix assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF-MS). The borate complexes of unsaturated acidic oligosaccharides having a 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid (4 delta UA) residue linked to a beta-D-(1-->4)-xylooligosaccharide backbone were separated by CZE and detected by their UV absorption at 232 nm without prior derivatization. Pre-column derivatization with the chromophore 6-aminoquinoline (6-AQ) followed by CZE in alkaline borate buffer using detection based on absorption at 245 nm was used in the case of neutral xylosaccharides. Furthermore, MALDI-TOF-MS was employed to determine the molecular masses of both unsaturated and saturated acidic oligosaccharides. The acidic oligosaccharides released upon endoxylanase treatment of the birch kraft pulp were a (4 delta UA)-beta-D-xylotetraose, a (4 delta UA)-beta-D-xylopentaose, a (4-O-methyl-alpha-D-glucurono)-beta-D-xylotetraose, and a (4-O-methyl-alpha-D-glucurono)-beta-D-xylopentaose. Analysis after enzymatic hydrolysis with beta-xylosidase and alpha-glucuronidase from Trichoderma reesei strongly indicated that the uronic acid residue in these acidic oligosaccharides was linked to the D-xylose unit adjacent to the non-reducing D-xylose unit. The neutral xylosaccharides obtained after endoxylanase treatment of the pulp sample were D-xylose, beta-(1-4)-D-xylobiose and beta-(1-4)-D-xylotriose.

Carbohydrate Sequence↗

PubMed1997

Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains.

Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method.

Acetylglucosaminidase↗

PubMed1998

Structural analysis of oligosaccharide-alditols released by reductive beta-elimination from oviducal mucins of Rana dalmatina.

The O-linked oligosaccharides of the jelly coat surrounding the eggs of Rana dalmantina were released by alkaline borohydride treatment. Low-molecular-mass, monosialyl oligosaccharide-alditols were isolated by anion-exchange chromatography and fractionated by consecutive normal-phase high-performance liquid chromatography on a silica-based alkylamine column. The structures of the oligosaccharide-alditols were determined by 400-MHz 1H-NMR spectroscopy in combination with matrix assisted laser desorption ionization-time of flight analysis. The five structures were identified range in size from trisaccharides to hexasaccharides, possessing a core consisting of Gal(beta 1-3)GalNAc-ol (core type 1). Novel oligosaccharide-alditols are: [formula: see text] The carbohydrate chains isolated from Rana dalmatina are different from those found in other amphibian species, in which the presence of species-specific material has been characterized. Since the role of carbohydrates appears more and more apparent during the fertilization process, the biodiversity of the O-linked oligosaccharides could support such a biological role.

Animals↗

PubMed1998

Enzymatic synthesis of N-linked oligosaccharides terminating in multiple sialyl-Lewis(x) and GalNAc-Lewis(x) determinants: clustered glycosides for studying selectin interactions.

Galactosyltransferase, sialyltransferase, and fucosyltransferase were used to create a panel of complex oligosaccharides that possess multiple terminal sialyl-Le(x) (NeuAc alpha 2-3Gal[Fuc alpha 1-3] beta 1-4GlcNAc) and GalNAc-Le(x) (GalNAc[Fuc alpha 1-3]beta 1-4GlcNAc). The enzymatic synthesis of tyrosinamide biantennary, triantennary, and tetraantennary N-linked oligosaccharides bearing multiple terminal sialyl-Le(x) was accomplished on the 0.5 mumol scale and the purified products were characterized by electrospray MS and 1H NMR. Likewise, biantennary and triantennary tyrosinamide oligosaccharides bearing multiple terminal GalNAc-Le(x) determinants were synthesized and similarly characterized. The transfer kinetics of human milk alpha 3/4-fucosyltransferase were compared for biantennary oligosaccharide acceptor substrates possessing Gal beta 1-4GlcNAc, GalNAc beta 1-4GlcNAc, and NeuAc alpha 2-3Gal beta 1-4GlcNAc which established NeuAc alpha 2-3Gal beta 1-4GlcNAc as the most efficient acceptor substrate. The resulting complex oligosaccharides were chemically tethered through the tyrosinamide aglycone to the surface of liposomes containing phosphatidylthioethanol, resulting in the generation of glycoliposomes probe which will be useful to study relationships between binding affinity and the micro- and macro-clustering of selectin ligand.

Acetylgalactosamine↗

PubMed1999

Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure.

Sulfated laminara-oligosaccharide glycosides having high anti-human immunodeficiency virus (HIV) activities were synthesized from laminara-tetraose, -pentaose and -hexaose. The oligosaccharide glycosides were synthesized by treating peracetylated beta-oligosaccharides with various alcohols and Lewis acid catalysts. The effects of the number of glucose residues and the alkyl chain-length on anti-HIV activity were examined. The anti-HIV activity of sulfated dodecyl laminara-pentaosides and -hexaosides increased with increasing degree of sulfation (DS) and the pentaoside having an almost fully-sulfated saccharide portion had the highest activity, whereas for the hexaoside a somewhat lower DS manifested the highest activity. Sulfated laminara-oligosaccharide glycosides having fluoroalkyl-containing aglycons of high hydrophobicity showed potent inhibitory effects against HIV infection. In contrast, hydrophilic substituents containing oligo(ethyleneoxy) groups as aglycons in the sulfated oligosaccharides did not show high anti-HIV activity.

Anti-HIV Agents↗

PubMed2002

Carbohydrate carriers affect adhesion of H. pylori to immobilized Leb-oligosaccharide.

The present study involved comparison of adhesion of Helicobacter pylori KH202 to immobilized Le(b)-oligosaccharide carried on different carriers, i.e. Leb-oligosaccharide conjugated with polyacrylamide, bovine serum albumin, and dipalmitoylphosphatidylethanolamine (Le(b)-PAA, Le(b)-BSA, and Le(b)-DPPE). All of the Le(b)-oligosaccharide-carrying neoglycoconjugates served as ligands for H. pylori. However, H. pylori required 10-fold and 100-fold quantities of Le(b)-antigen to adhere to Le(b)-PAA and to Le(b)-DPPE in comparison to the quantity of Le(b)-antigen needed to adhere to Le(b)-BSA, respectively. H. pylori adhesion to Le(b)-PAA and Le(b)-DPPE was clearly inhibited by Le(b)-oligosaccharide, but adhesion to Le(b)-BSA was hardly inhibited by the oligosaccharide. Therefore, the carbohydrate carrier affects the affinity of H. pylori KH202 toward Le(b)-antigen, although the bacteria recognize Le(b)-antigen regardless of the carbohydrate carrier.

Acrylic Resins↗

PubMed2003

Separation of a complex mixture of heparin-derived oligosaccharides using reversed-phase high-performance liquid chromatography.

A reversed-phase ion-pairing high-performance liquid chromatography (RP-HPIPC) method for the separation of a complex mixture of heparin-derived oligosacchrides has been developed by a stepwise optimization of the mobile phase, in which the concentration of ion-pairing reagent, mobile phase pH, and acetonitrile concentration were varied. The resolution of more than 30 oligosaccharide components was obtained, under optimized conditions, in an analysis time of less than 30 min. This represents the first RP-HPLC method that can separate a complex mixture of both small and large sulfated oligosaccharides in a single chromatographic step. The heparin-derived oligosaccharides, in this mixture, can also be separated under a second set of RP-HPIPC conditions using a volatile ion-pairing reagent, tributylammonium acetate, to aid in the recovery of individual sulfated oligosaccharides. Moreover, it was possible to replace sodium chloride gradient, required for eluting highly sulfated oligosaccharides, with a fixed, low concentration of a volatile salt, ammonium acetate, by utilizing an acetonitrile gradient. This solvent system might make it possible to directly interface this RP-HPIPC separation with mass spectral analysis.

Chromatography, High Pressure Liquid↗

PubMed2003

Capillary electrophoretic separation of heparin oligosaccharides under conditions amenable to mass spectrometric detection.

A capillary electrophoresis method for the separation of high-molecular-mass heparin oligosaccharides compatible with mass spectral detection was developed. Structurally defined heparin oligosaccharides ranging in size from tetrasaccharide to tetradecasaccharide were used to optimize the conditions. Applying normal and reversed polarity modes, these oligosaccharides were separated by CE under various conditions. Ammonium hydrogencarbonate (30 mM at pH 8.50) used as the running electrolyte system gave good separation efficiency and resolution in the normal polarity mode. Application of this method to the separation of complicated heparin oligosaccharide mixtures required the addition of electrolyte additives. Ammonium hydrogencarbonate (30 mM), containing triethylamine (10 mM), was useful for the separation of complex oligosaccharide mixtures. Run-to-run and day-to-day precision and limits of detection were established for these separations.

Electrophoresis, Capillary↗

PubMed1999

Size determination of bacterial capsular oligosaccharides used to prepare conjugate vaccines.

We recently described the use of ion exchange chromatography for analysis and the industrial scale preparation of pools of oligosaccharides of intermediate chain length from polysaccharides of Haemophilus influenzae type b (Hib) and Neisseria meningitidis groups A and C. These negatively charged "sized" oligosaccharides are activated and conjugated to the carrier protein (CRM197) to prepare the corresponding glycoconjugate vaccines. Characterization and accurate determination of the degree of polymerization (DP) of the pool of oligosaccharides is essential for the consistent production of these conjugate vaccines. This paper describes the colorimetric assays used for determination of the average DP of the Hib and meningococcal oligosaccharides, and the qualification of these assays achieved by size characterization of the respective oligosaccharides by use of physicochemical methods, including liquid chromatography, mass spectrometry (ionspray) and NMR spectroscopy.

Bacterial Capsules↗

PubMedDate not supplied

Sulfated oligosaccharides isolated from the respiratory mucins of a secretor patient suffering from chronic bronchitis.

The most acidic carbohydrate chains released by alkaline borohydride treatment of the bulk of airway mucins secreted by a patient (blood group O, secretor) suffering from a mildly infected chronic bronchitis have been fractionated using high-performance anion-exchange chromatography (HPAEC) according to a protocol already described [Lo-Guidice et al., J. Biol. Chem. 269 (1994) 18794] and were analyzed using 1H-NMR spectroscopy and matrix-assisted laser-adsorption-time-of-flight (MALDI-TOF) spectrometry. Many fractions corresponded to mixtures of oligosaccharides. This confirmed the wide diversity of the post-translational processes involved in the biosynthesis of airway mucins, which had already been observed in bronchial diseases, such as chronic bronchitis and cystic fibrosis (CF). Seven fractions were directly purified by HPAEC, allowing their structural determination. Six of them corresponded to 3-O-sulfated oligosaccharide chains terminated by a sulfated N-acetyllactosamine, a sulfated Lewis X or a sulfated Lewis A determinant, and the last one corresponded to a 6-O-sulfated chain terminated by a sulfated H-2 determinant. Three oligosaccharides had core type 2 and the other four had core type 4: IIIc2-9: Gal(beta1-3)[HSO(3)-3-Gal(beta1-4)GlcNAc(beta1-6)]GalNAc-ol, IIIc2-10: Gal(beta1-3)[Fuc(alpha1-2)Gal(beta1-4)[HSO(3)-6-]GlcNAc(beta1-6)]GalNAc-ol, IIIc2-4: Fuc(alpha1-2)Gal(beta1-3)[HSO(3)-3-Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-6)]GalNAc-ol, IIIc2-8: Fuc(alpha1-2)Gal(beta1-3)GlcNAc(beta1-3)[HSO(3)-3-Gal(beta1-4)GlcNAc(beta1-6)]GalNAc-ol, IIIc2-7: Fuc(alpha1-2)Gal(beta1-3)GlcNAc(beta1-3)[Gal(beta1-4)[HSO(3)-6-]GlcNAc(beta1-6)]GalNAc-ol, IIIc2-3: Fuc(alpha1-2)Gal(beta1-3)GlcNAc(beta1-3)[HSO(3)-3-Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-6)]GalNAc-ol, IIIc1-4: Fuc(alpha1-2)Gal(beta1-3)GlcNAc(beta1-3)[HSO(3) -3-Gal(beta1-3)[Fuc(alpha1-4)]GlcNAc(beta1-3)Gal(beta1-4)GlcNAc(beta1-6)]GalNAc-ol. Like previous data concerning the airway mucins from another patient (blood group O and non-secretor) suffering from chronic bronchitis [Lo-Guidice et al., Glycoconj. J. 14 (1997) 113], no disialylated oligosaccharide and no sialylated and sulfated oligosaccharide bearing sialyl Lewis X epitope could be isolated. This is in contrast with the data obtained with the airway mucins secreted by the patient severely infected by Pseudomonas aeruginosa and suffering from CF, suggesting that important differences occur in the biosynthesis of airway mucins secreted by patients suffering from different bronchial diseases with or without severe infection.

Bronchitis↗

PubMed1975

[Isolation and physico-chemical properties of oligosaccharides of human milk].

From a non-dialysable fraction of human milk the authors have isolated 30 oligosaccharides by combining anion exchange and paper chromatography. These oligosaccharides (MW 998 to 3113) contain D (+)-galactose, L (-)-fucose, N-acetyl-D (+)-glucosamine, N-acetyl-D (-)-neuraminic acid in variable proportions and one single D (+)-glucose residue in terminal reducing position. The characteristics of the oligosaccharides are those of the so-called "Polonovski and Lespagnol gynolactose". These sugars do not originate from glycoproteins nor glycolipids. The authors suggest that the biosynthesis of human milk oligosaccharides is due to an activation of glycosyltransferases related to blood group substances, induced by lactose. They base this hypothesis on the fact that, as demonstrated by Strecker and Montreuil, spontaneous or glucose, galactose and lactose induced meliturias are accompagnied by an important urinary excretion of blood group substance related oligosaccharides.

Acetylglucosamine↗

PubMed2000

Chemical characterization of milk oligosaccharides of the polar bear, Ursus maritimus.

Two trisaccharides, three tetrasaccharides, two pentasaccharides, one hexasaccharide, one heptasaccharide, one octasaccharide and one decasaccharide were isolated from polar bear milk samples by chloroform/methanol extraction, gel filtration, ion exchange chromatography and preparative thin-layer chromatography. The oligosaccharides were characterized by 1H-NMR as follows: the saccharides from one animal: Gal(alpha1-3)Gal(beta1-4)Glc (alpha3'-galactosyllactose), Fuc(alpha1-2)Gal(beta1-4)Glc (2'-fucosyllactose), Gal(alpha1-3)[Fuc(alpha1-2)]Gal(beta1-4)Glc (B-tetrasaccharide), GalNAc(alpha1-3)[Fuc(alpha1-2)]Gal(beta1-4)Glc (A-tetrasaccharide), Gal(alpha1-3)Gal(beta1-4)GlcNAc(beta1-3)Gal(beta1-4)Glc, Gal(alpha1-3)[Fuc(alpha1-2)]Gal(beta1-4)GlcNAc(beta1-3)Gal(beta1-4)Gl c, Gal(alpha1-3)Gal(beta1-4)GlcNAc(beta1-3)[Gal(alpha1-3)Gal(beta1-4)Glc NAc(beta1-6)]Gal(beta1-4)Glc; the saccharides from another animal: alpha3'-galactosyllactose, Gal(alpha1-3)Gal(beta1-4)[Fuc(alpha1-3)]Glc, A-tetrasaccharide, GalNAc(alpha1-3)[Fuc(alpha1-2)]Gal(beta1-4)[Fuc(alpha1-3)]Glc (A-pentasaccharide), Gal(alpha1-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)Gal(beta1-4)Gl c, Gal(alpha1-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)Gal(beta1-4)[F uc(alpha1-3)]Glc (difucosylheptasaccharide) and Gal(alpha1-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)¿Gal(alpha1-3) Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-6)¿Gal(beta1-4)Glc (difucosyldecasaccharide). Lactose was present only in small amounts. Some of the milk oligosaccharides of the polar bear had alpha-Gal epitopes similar to some oligosaccharides in milk from the Ezo brown bear and the Japanese black bear. Some milk oligosaccharides had human blood group A antigens as well as B antigens; these were different from the oligosaccharides in Ezo brown and Japanese black bears.

Animals↗

PubMed1998

The involvement of mnn4 and mnn6 mutations in mannosylphosphorylation of O-linked oligosaccharide in yeast Saccharomyces cerevisiae.

The structure of O-linked acidic oligosaccharide from Saccharomyces cerevisiae was analyzed. The chitinase, exclusively O-glycosylated extracelluar protein, was purified from strains mnn1, mnn1 mnn4, mnn1 mnn6 and deltakre2 and the oligosaccharides were hydrolyzed by O-linked sugar chain specific hydrazinolysis. The mannosylphosphorylated mannotriose (M3-P-M) was detected in strain mnn1, but not in the other three strains (mnn1n mnn4, mnn1 mnn6 and deltakre2). alpha-Mannosidase treatment and matrix-assisted laser desorption ionization time-of-flight mass spectrometry of mannosylphosphorylated mannotriose revealed that mannosylphosphate was attached to a middle mannose of alpha-1,2-linked mannotriose. This result indicates that the mnn4 and mnn6 mutations affect the mannosylphosphorylation of O-linked oligosaccharide, together with that of N-linked oligosaccharide. The amount of mannosylphosphorylated mannotriose was 7% of total O-linked oligosaccharides (20% of neutral mannotriose) of chitinase in strain mnn1.

Alkaline Phosphatase↗

PubMed1996

High-pH anion-exchange chromatography with pulsed amperometric detection and molar response factors of human milk oligosaccharides.

A method is described to separate and characterize neutral and acidic lactose-derived oligosaccharides without prior derivatization or reduction by high-pH anion-exchange chromatography and pulsed amperometric detection (HPAEC-PAD). This method has been applied to human milk oligosaccharides from donors with different blood group specificity (A, Le(a) and A, Le(b). Neutral and acidic components were separated from each other by anion-exchange chromatography. A distinct separation of individual components was obtained by size-exclusion chromatography on Fractogel TSK HW 50S (acidic oligosaccharides) or Fractogel TSK HW 40S (neutral oligosaccharides containing up to 6 monomers) and Bio-Gel P-4 size exclusion (neutral oligosaccharides containing more than 6 monomers). Furthermore the moral response factors after HPAEC-PAD have been determined for 28 components.

Carbohydrate Sequence↗

PubMed1998

The glycosylation sites and structural characteristics of oligosaccharides on recombinant human thrombomodulin.

Thrombomodulin (TM) is an anticoagulant glycoprotein on the surface of endothelial cell that directly inhibits the procoagulant activities of thrombin, and the TM-thrombin complex accelerates thrombin-catalyzed activation of protein C. Soluble TM in urine has no glycosaminoglycan (GAG) chain which accelerates the anticoagulant activities. Therefore, we expressed recombinant GAG-modified urinary thrombomodulin (GAG-UTM) in C127 cells. The glycosylation sites were determined by amino acid sequence analysis of peptides digested with trypsin after S-carboxymethylation. The structures of N-linked oligosaccharides were estimated by two-dimensional sugar mapping of pyridylaminated oligosaccharides that were treated with exoglycosidase. The disaccharide composition analysis of the GAG chain was performed by HPLC using digestion with chondroitinase ABC, ACII and B. Consequently, it was revealed that the N-linked oligosaccharides were assigned to Asn29, Asn98, Asn364, Asn391; those structures were estimated biantennary, 2-6 branched triantennary and 2-4 branched triantennary complex type oligosaccharides that were linked by fucose at the ratio of 1.0:0.5:0.1, respectively. Moreover, the attachment site of the GAG chain was assigned to Ser472. It was then estimated that the GAG chain contained chondroitin-4-sulfate and dermatan sulfate, which were repeated approximately 30 times. In this paper, the GAG attachment site and structural characteristics of GAG-UTM, were confirmed. Moreover, structures of the N-linked oligosaccharides of GAG-UTM are described for the first time.

Amino Acid Sequence↗

PubMed2000

Oligosaccharides and glycoconjugates in bovine milk and colostrum.

Oligosaccharides and glycoconjugates are some of the most important bioactive components in milk. A great deal of information is available on the biological function of the components from human milk. Their primary role seems to be in providing protection against pathogens by acting as competitive inhibitors for the binding sites on the epithelial surfaces of the intestine. Evidence is also available to support the role of some of these components as growth promoters for genera of beneficial microflora in the colon. Compared with human milk, levels of oligosaccharides in bovine milk are very low. Nevertheless, a number of neutral and acidic oligosaccharides have been isolated from bovine milk and characterised. The highest concentration of these molecules is found in early postparturition milk (colostrum). The chemical structure of the oligosaccharides and many of the glycoconjugates from bovine milk are similar to those in human milk. It is likely that bovine oligosaccharides and glycoconjugates can be used in milk products as bioactive components in human nutrition.

Animals↗