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Proc Jpn Acad Ser B Phys Biol Sci
2016 Jan 01;924:109-20. doi: 10.2183/pjab.92.109.
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Sialic acids as link to Japanese scientists.
Schauer R
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This manuscript is dedicated to Prof. Tamio Yamakawa and describes my cooperations on sialic acid-related topics with Japanese scientists during the last 40 years. We studied sialic acids and their O-acetylated derivatives in the sea urchin Pseudocentrotus depressus, in Halocynthia species, and in human and bovine milk. In seafood we mainly searched for N-glycolylneuraminic acid. With synthetic substrates it was shown that sialic acid O-acetylation at C-4 hinders the activity of sialidases, with the exception of viral enzymes. The biosynthesis of Neu5Gc was discussed and the distribution of this sialic acid in dogs followed in modern literature and reviewed regarding their migration. An excellent source of sialic acids is edible bird nest substance (Collocalia mucin) which was used for the synthesis of sialylation inhibitors.
Figure 1. . Structures of the three most frequently occurring sialic acids N-acetylneuraminic acid, N-glycolylneuraminic acid, and N-acetyl-9-O-acetylneuraminic acid. Neu5Ac is the mother molecule of the other Sia. O-Acetyl residues occur at C-4, C-7, C-8, and C-9 of Neu5Ac and Neu5Gc. The 9-hydroxyl can be lactylated or phosphorylated and at C-8 a sulfate or a methyl group can be found in some biological materials.3,4)
Figure 2. . Halocynthia aurantium (left) and H. roretzi (right). Courtesy of Prof. Kazuhiko Konishi.
Figure 3. . Course of the concentration of N-acetylneuraminic acid (right) and N-acetyl-9-O-acetylneuraminic acid (left) in human milk during lactation.
Figure 4. . Fluorimetric HPLC analysis of sialic acids in a sample of human milk.3) A: Run of acid-liberated free Sia. B: After aldolase (sialate-pyruvate lyase) treatment of this sample, which splits Sia into pyruvate and acylmannosamine, the Sia peaks were much smaller, showing the authenticity of these Sia peaks.
Figure 5. . Course of the concentration of N-acetylneuraminic acid (right) and N-acetyl-9-O-acetylneuraminic acid (left) in bovine milk during lactation.
Figure 6. . Geographical distribution of dogs and related animals and their migration indicating the possible origin of Japanese dogs (red).44) The figure is reused from the proceedings of the Japan Academy, Ser. B, with permission of the publishers.
Figure 7. . Scanning electron microscopy of sialidase-treated rat thrombocytes bound to homologous peritoneal macrophages. The breadth of the picture corresponds to 15 µm.
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