Bovine Milk Glycome

Nanoelectrospray ionization Fourier transform ion cyclotron resonance mass spectra obtained from pooled bovine milk oligosaccharides (A) in positive mode and (B) in negative mode. Table inserts correspond to the composition of the masses.

High-performance liquid chromatography-chip time-of-flight chromatograms of pooled human milk oligosaccharide (A) and bovine milk oligosaccharide (B) samples in the positive mode. The most abundant signal in the bovine sample corresponded to sialyllactose.

Infrared multiphoton dissociation spectra of ions with composition corresponding to A) m/z 732.253 [3Hex+1HexNAc+Na]⁺; B) m/z 894.306 [4Hex+1HexNAc+Na]⁺; and C) m/z 1161.405 [4Hex+1HexNAc+1NeuAc-H]^-. The peaks are labeled with the corresponding fragment structures. Hex = hexose; HexNAc = N-acetylhexosamine; NeuAc = N-acetyl neuraminic acid.

Extracted ion chromatograms for ions with m/z 1,074.396 in bovine milk (BMO), human milk (HMO), and standard mixtures [lacto-N-hexaose (LNH) and lacto-N-neohexaose (LNnH)]. M = m/z; Hex = hexose; HexNAc = N-acetylhexosamine; NeuAc = N-acetyl neuraminic acid.

Possible structures of bovine milk oligosaccharides with relative abundance and retention times. Numbers marked shows references source; T = tandem MS available; P = new proposed structures (i.e., not found in reference or tandem MS, but proposed based on other known similar structures); ○ and ● indicate glucose (Glc) and galactose (Gal), respectively; □ and ■ represent N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc), respectively; and ♢ and ♦ indicate N-acetyl neuraminic acid (NeuAc) and N-glycolylneuraminic acid (NeuGc), respectively. Exptl = experimental; cal = calculated; Hex = hexose; HexNAc = N-acetylhexosamines; NeuAc = N-acetylneuraminic acid; and NeuGc = N-glycolylneuraminic acid. Possible structures of bovine milk oligosaccharides with relative abundance and retention times. Numbers marked shows references source; T = tandem MS available; P = new proposed structures (i.e., not found in reference or tandem MS, but proposed based on other known similar structures); ○ and ● indicate glucose (Glc) and galactose (Gal), respectively; ■ and □ represent N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc), respectively; and ♢ and ♦ indicate N-acetyl neuraminic acid (NeuAc) and N-glycolylneuraminic acid (NeuGc), respectively. Exptl = experimental; cal = calculated; Hex = hexose; HexNAc = N-acetylhexosamines; NeuAc = N-acetylneuraminic acid; and NeuGc = N-glycolylneuraminic acid.

Possible structures of bovine milk oligosaccharides with relative abundance and retention times. Numbers marked shows references source; T = tandem MS available; P = new proposed structures (i.e., not found in reference or tandem MS, but proposed based on other known similar structures); ○ and ● indicate glucose (Glc) and galactose (Gal), respectively; □ and ■ represent N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc), respectively; and ♢ and ♦ indicate N-acetyl neuraminic acid (NeuAc) and N-glycolylneuraminic acid (NeuGc), respectively. Exptl = experimental; cal = calculated; Hex = hexose; HexNAc = N-acetylhexosamines; NeuAc = N-acetylneuraminic acid; and NeuGc = N-glycolylneuraminic acid. Possible structures of bovine milk oligosaccharides with relative abundance and retention times. Numbers marked shows references source; T = tandem MS available; P = new proposed structures (i.e., not found in reference or tandem MS, but proposed based on other known similar structures); ○ and ● indicate glucose (Glc) and galactose (Gal), respectively; ■ and □ represent N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc), respectively; and ♢ and ♦ indicate N-acetyl neuraminic acid (NeuAc) and N-glycolylneuraminic acid (NeuGc), respectively. Exptl = experimental; cal = calculated; Hex = hexose; HexNAc = N-acetylhexosamines; NeuAc = N-acetylneuraminic acid; and NeuGc = N-glycolylneuraminic acid.