Structural determination of the oligosaccharides in the milk of an Asian elephant (Elephas maximus)

Milk of an Asian elephant (Elephas maximus), collected at 11 days post partum, contained 91 g/L of hexose and 3 g/L of sialic acid. The dominant saccharide in this milk sample was lactose, but it also contained isoglobotriose (Glc(alpha1-3)Gal(beta1-4)Glc) as well as a variety of sialyl oligosaccharides. The sialyl oligosaccharides were separated from neutral saccharides by anion exchange chromatography on DEAE-Sephadex A-50 and successive gel chromatography on Bio Gel P-2. They were purified by high performance liquid chromatography (HPLC) using an Amide-80 column and characterized by 1H-NMR spectroscopy. Their structures were determined to be those of 3'-sialyllactose, 6'-sialyllactose, monofucosyl monosialyl lactose (Neu5Ac(alpha2-3)Gal(beta1-4)[Fuc(alpha1-3)]Glc), sialyl lacto-N-neotetraose c (LST c), galactosyl monosialyl lacto-N-neohexaose, galactosyl monofucosyl monosialyl lacto-N-neohexaose and three novel oligosaccharides as follows: Neu5Ac(alpha2-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)Gal(beta1-4)Glc, Neu5Ac(alpha2-6)Gal(beta1-4)GlcNAc(beta1-3)Gal(beta1-4)GlcNAc(beta1-3)Gal(beta1-4)Glc, and Neu5Ac(alpha2-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-3)Gal(beta1-4)Glc. The higher oligosaccharides contained only the type II chain (Gal(beta1-4)GlcNAc); this finding differed from previously published data on Asian elephant milk oligosaccharides.     

Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents

The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylphenoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency.     

Differences in oligosaccharide pattern of a sample of polar bear colostrum and mid-lactation milk

Although the concentrations of carbohydrate in the colostrum and in the mid-lactation milk of polar bear (Ursus maritimus) were similar, the oligosaccharide patterns differed. The colostrum sample contained Neu5Ac(α2-3)Gal(β1-4)Glc (3′-N-acetylneuraminyllactose), GalNAc(α1-3)[Fuc(α1-2)]Gal(β1-4)Glc (A-tetrasaccharide), Fuc(α1-2)Gal(β1-4)Glc (2′-fucosyllactose) and Gal(β1-4)Glc (lactose). The mid-lactation milk contained Gal(α1-3)[Fuc(α1-2)]Gal(β1-4)[Fuc(α1-3)]Glc (B-pentasaccharide), GalNAc(α1-3)[Fuc(α1-2)]Gal(β1-4)[Fuc(α1-3)]Glc (A-pentasaccharide), Gal(α1-3)[Fuc(α1-2)]Gal(β1-4)Glc (B-tetrasaccharide), A-tetrasaccharide, Gal(α1-3)Gal(β1-4)[Fuc(α1-3)]Glc (3-fucosylisoglobotriose), Gal(α1-3)Gal(β1-4)Glc (isoglobotriose) and lactose. The dominant saccharides in the colostrum were 3′-N-Acetylneuraminyllactose and lactose, whereas isoglobotriose was the dominant saccharide in the mid-lactation milk in which lactose was only a minor component. Isoglobotriose, which had previously been found to be a dominant saccharide in mature milk from the Ezo brown bear, the Japanese black bear and the polar bear, was not found in the polar bear colostrum.