Advanced technologies in sialic acid and sialoglycoconjugate analysis

Topics in Current Chemistry

Volumn 367, Issue , 2015, Pages 75-104

  Kitajima, Ken ^a   Varki, Nissi ^b   Sato, Chihiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chemical analysis; Deaminoneuraminic acid; Disialic acid; DMB derivatization; Immunochemical analysis; Immunohistochemistry; N Glycolylneuraminic acid; O Acetylated sialic acid; O Sulfated sialic acid; Oligosialic acid; Polysialic acid

Indexed keywords

GLYCOCONJUGATE; GLYCOLIPID; GLYCOPROTEIN; N ACETYLNEURAMINIC ACID; N-GLYCOLYLNEURAMINIC ACID; NEURAMINIC ACID DERIVATIVE; OLIGOSACCHARIDE; POLY(2,8-DEAMINONEURAMINIC ACID); POLYSACCHARIDE; POLYSIALIC ACID; SIALIC ACID DERIVATIVE; SIALOOLIGOSACCHARIDES;

AGING; CARCINOGENESIS; CHEMISTRY; DEVICES; FLUOROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IMMUNOHISTOCHEMISTRY; INNATE IMMUNITY; METABOLISM; NERVOUS SYSTEM DEVELOPMENT; PATHOLOGY; PHYSIOLOGY; PROCEDURES;

AGING; CARCINOGENESIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUOROMETRY; GLYCOCONJUGATES; GLYCOLIPIDS; GLYCOPROTEINS; HUMANS; IMMUNITY, INNATE; IMMUNOHISTOCHEMISTRY; N-ACETYLNEURAMINIC ACID; NEURAMINIC ACIDS; NEUROGENESIS; OLIGOSACCHARIDES; POLYSACCHARIDES; SIALIC ACIDS;

EID: 84938336591     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2013_458     Document Type: Article

References (111)

1. Angata T, Varki A (2002) Chemical diversity in the sialic acid and related α-keto acids: an evolutionary perspective. Chem Rev 102:439-469
2. Schauer R, Kamerling JP (2003) In: Montreuil J, Vliegenthart JFG, Schachter H (eds) Chemistry, biochemistry and biology of sialic acid, glycoproteins II. Elsevier, Amsterdam, pp 243-402
3. Varki A (1997) Sialic acids as ligands in recognition phenomena. FASEB J 11:248-255
4. Varki A, Hooshmand F, Diaz S, Varki NM, Hedrick SM (1991) Developmental abnormalities in transgenic mice expressing a sialic acid-specific 9-O-acetylesterase. Cell 65:65-74
5. Cariappa A, Takematsu H, Liu H, Diaz S, Haider K, Boboila C, Kalloo G, Connole M, Shi HN, Varki N, Varki A, Pillai S (2009) B cell antigen receptor signal strength and peripheral B cell development are regulated by a 9-O-acetyl sialic acid esterase. J Exp Med 206:125-138
6. Parameswaran R, Lim M, Arutyunyan A, Abdel-Azim H, Hurtz C, Lau K, Müschen M, Yu RK, von Itzstein M, Heisterkamp N, Groffen J (2013) O-Acetylated N-acetylneuraminic acid as a novel target for therapy in human pre-B acute lymphoblastic leukemia. J Exp Med 210:805-819
7. Mandal C, Schwartz-Albiez R, Vlasak R (2011) Functions and biosynthesis of O-acetylated sialic acids. Top Curr Chem. doi:10.1007/128_2011_310
8. Davies LRL, Varki A (2013) Why is N-glycolylneuraminic acid rare in the vertebrate brain? Top Curr Chem. doi:10.1007/128_2013_419
9. Hildebrandt H, Dityatev A (2013) Polysialic acid in brain development and synaptic plasticity. Top Curr Chem. doi:10.1007/128_2013_446
10. Wipfler D, Srinivasan GV, Sadick H, Kniep B, Arming S, Willhauck-Fleckenstein M, Vlasak R, Schauer R, Schwartz-Albiez R (2011) Differentially regulated expression of 9-O-acetyl GD3 (CD60b) and 7-O-acetyl-GD3 (CD60c) during differentiation and maturation of human T and B lymphocytes. Glycobiology 21:1161-1172
11. Lrhorfi LA, Srinivasan GV, Schauer R (2007) Properties and partial purification of sialate O-acetyltransferase from bovine submandibular glands. Biol Chem 388:297-306
12. Higa HH, Diaz S, Varki A (1987) Biochemical and genetic evidence for distinct membranebound and cytosolic sialic acid O-acetyl-esterases: serine-active-site enzymes. Biochem Biophys Res Commun 144:1099-1108
13. Shen Y, Kohla G, Lrhorfi AL, Sipos B, Kalthoff H, Gerwing GJ, Kamerling JP, Schauer R, Tiralongo J (2004) O-Acetylation and de-O-acetylation of sialic acids in human colorectal carcinoma. Eur J Biochem 271:281-290
14. Schauer R, Shukla AK (2008) Isolation and properties of two sialate-O-acetylesterases from horse liver with 4- and 9-O-acetyl specificities. Glycoconj J 25:625-632
15. Schwardt O, Kelm S, Ernst B (2013) SIGLEC4 antagonists. Top Curr Chem. doi:10.1007/ 128_2013_498
16. Chou HH, Takematsu H, Diaz S, Iber J, Nickerson E, Wright KL, Muchmore EA, Nelson DL, Warren ST, Varki A (1998) A mutation in human CMP-sialic acid hydroxylase occurred after the Homo-Pan divergence. Proc Natl Acad Sci USA 95:11751-11756
17. Irie A, Koyama S, Kozutsumi Y, Kawasaki T, Suzuki A (1998) The molecular basis for the absence of N-glycolylneuraminic acid in humans. J Biol Chem 273:15866-15871
18. Taylor RE, Gregg CJ, Padler-Karavani V, Ghaderi D, Yu H, Huang S, Sorensen RU, Chen X, Inostroza J, Nizet V, Varki A (2010) Novel mechanism for the generation of human xenoautoantibodies against the nonhuman sialic acid N-glycolylneuraminic acid. J Exp Med 207:1637-1646
19. Hedlund M, Padler-Karavani V, Varki NM, Varki A (2008) Evidence for a human-specific mechanism for diet and antibody-mediated inflammation in carcinoma progression. Proc Natl Acad Sci USA 105:18936-18941
20. Pham T, Gregg CJ, Karp F, Chow R, Padler-Karavani V, Cao H, Chen X, Witztum JL, Varki NM, Varki A (2009) Evidence for a novel human-specific xeno-auto-antibody response against vascular endothelium. Blood 114:5225-5235
21. Shilova N, Huflejt ME, Vuskovic M, Obukhova P, Navakouski M, Khasbiullina N, Pazynina G, Galanina O, Bazhenov A, Bovin N (2013) Natural antibodies against sialoglycans. Top Curr Chem. doi:10.1007/128_2013_469
22. Nadano D, Iwasaki M, Endo S, Kitajima K, Inoue S, Inoue Y (1986) A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs. J Biol Chem 261:11550-11557
23. Inoue S, Kitajima K (2006) KDN (deaminated neuraminic acid): dreamful past and exciting future of the newest member of the sialic acid family. Glycoconj J 23:277-290
24. Inoue S, Kitajima K, Inoue Y (1996) Identification of 2-keto-3-deoxy-D-glycero-D-galactonononic acid (KDN, deaminoneuraminic acid) residues in mammalian tissues and human lung carcinoma cells. Chemical evidence of the occurrence of KDN glycoconjugates in mammals. J Biol Chem 271:24341-24344
25. Go S, Sato C, Yin J, Kannagi R, Kitajima K (2007) Hypoxia-enhanced expression of free deaminoneuraminic acid in human cancer cells. Biochem Biophys Res Commun 357:537-542
26. Prokazova NV, Mikhailov AT, Kocharov SL, Malchenko LA, Zvezdina ND, Buznikov G, Bergelson LD (1981) Unusual gangliosides of eggs and embryos of the sea urchin Strongylocentrotus intermedius. Structure and density-dependence of surface localization. Eur J Biochem 115:671-677
27. Kochetkov NK, Smimova GP, Chekareva NV (1976) Isolation and structural studies of a sulfated sialosphingolipid from the sea urchin Echinocardium cordatum. Biochim Biophys Acta 424:274-283
28. Kubo H, Irie A, Inagaki F, Hoshi M (1990) Gangliosides from the eggs of the sea urchin, Anthocidaris crassispina. J Biochem (Tokyo) 108:185-192
29. Ijuin T, Kitajima K, Song Y, Kitazume S, Inoue S, Haslam SM, Morris HR, Dell A, Inoue Y (1996) Isolation and identification of novel sulfated and nonsulfated oligosialyl glycosphingolipids from sea urchin sperm. Glycoconj J 13:401-413
30. Kitazume S, Kitajima K, Inoue S, Haslam SM, Morris HR, Dell A, Lennarz WJ, Inoue Y (1996) The occurrence of novel 9-O-sulfated N-glycolylneuraminic acid-capped α2!5- Oglycolyl-linked oligo/polyNeu5Gc chains in sea urchin egg cell surface glycoprotein. Identification of a new chain termination signal for polysialyltransferase. J Biol Chem 22:6694-6701
31. Miyata S, Sato C, Kitamura S, Toriyama M, Kitajima K (2004) A major flagellum sialoglycoprotein in sea urchin sperm contains a novel polysialic acid, an α2,9-linked poly-N- acetylneuraminic acid chain, capped by an 8-O-sulfated sialic acid residue. Glycobiology 14:827-840
32. Miyata S, Sato C, Kumita H, Toriyama M, Vacquier VD, Kitajima K (2006) Flagellasialin: a novel sulfated α2,9-linked polysialic acid glycoprotein of sea urchin sperm flagella. Glycobiology 16:1229-1241
33. Slomiany BL, Kojima K, Banas-Gruszka Z, Murty VL, Galicki NI, Slomiany A (1981) Characterization of the sulfated monosialosyltriglycosylceramide from bovine gastric mucosa. Eur J Biochem 119:647-650
34. Slomiany A, Kojima K, Banas-Gruszka Z, Slomiany BL (1981) Structure of a novel sulfated sialoglycosphingolipid from bovine gastric mucosa. Biochem Biophys Res Commun 100:778-784
35. Morimoto N, Nakano M, Kinoshita M, Kawabata A, Morita M, Oda Y, Kuroda R, Kakehi K (2001) Specific distribution of sialic acids in animal tissues as examined by LC-ESI-MS after derivatization with 1,2-diamino-4,5-methylenedioxybenzene. Anal Chem 73:5422-5428
36. Bulai T, Bratosin D, Pons A, Montreuil J, Zanetta JP (2003) Diversity of the human erythrocyte membrane sialic acids in relation with blood groups. FEBS Lett 534:185-189
37. Kawai Y, Takemoto M, Oda Y, Kakehi K, Ohta Y, Yamaguchi S, Miyake M (2000) Inhibition of in vitro fertilization of mouse gametes by sulfated sialic acid polymers. Biol Pharm Bull 23:936-940
38. Kimura K, Mori S, Tomita K, Ohno K, Takahashi K, Shigeta S, Terada M (2000) Antiviral activity of NMSO3 against respiratory syncytial virus infection in vitro and in vivo. Antiviral Res 47:41-51
39. Kisa F, Yamada K, Miyamoto T, Inagaki M, Higuchi R (2007) Determination of the absolute configuration of sialic acids in gangliosides from the sea cucumber Cucumaria echinata. Chem Pharm Bull(Tokyo) 55:1051-1052
40. Bhattacharjee AK, Jennings HJ, Kenny CP, Martin A, Smith IC (1976) Structural determination of the polysaccharide antigens of Neisseria meningitidis serogroups Y, W-135, and BO1. Can J Biochem 54:1-8
41. Sato C, Kitajima K (2011) New functions of polysialic acid and its relationship to schizophrenia. Trends Glycosci Glycotechnol 23:221-238
42. Mühlenhoff M, Rollenhagen M, Werneburg S, Gerardy-Schahn R, Hildebrandt H (2013) Polysialic acid: versatile modification of NCAM, SynCAM 1 and Neuropilin-2. Neurochem Res doi:10.1007/s11064-013-0979-2
43. Sato C (2013) Polysialic acid. In: Tiralongo J, Martinez-Duncker I (eds) Sialobiology: structure, biosynthesis, and function, Bentham Science, pp 33-75. http://www.eurekaselect. com/107046/volume/1
44. Rutishauser U (2008) Polysialic acid in the plasticity of the developing and adult vertebrate nervous system. Nat Rev Neurosci 9:26-35
45. Kanato Y, Kitajima K, Sato C (2008) Complex formation of a brain-derived neurotrophic factor and glycosaminoglycans. Glycobiology 18:1044-1053
46. Kanato Y, Ono S, Kitajima K, Sato C (2009) Direct binding of polysialic acid to a brainderived neurotrophic factor depends on the degree of polymerization. Biotech Biosci Biochem 73:2735-2741
47. Sato C, Yamakawa N, Kitajima K (2010) Measurement of glycan-based interactions by frontal affinity chromatography and surface plasmon resonance. Methods Enzymol 478:219-232
48. Isomura R, Kitajima K, Sato C (2011) Structural and functional impairments of polysialic acid by a mutated polysialyltransferase found in schizophrenia. J Biol Chem 286:21535-21545
49. Ono S, Hane M, Kitajima K, Sato C (2012) Novel regulation of FGF2-mediated cell growth by polysialic acid. J Biol Chem 287:3710-3722
50. Vaithianathan T, Matthias K, Bahr B, Schachner M, Suppiramaniam V, Dityatev A, Steinhaüser C (2004) Neural cell adhesion molecule-associated polysialic acid potentiates α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor currents. J Biol Chem 279:47975-47984
51. Hammond MS, Sims C, Parameshwaran K, Suppiramaniam V, Schachner M, Dityatev A (2006) Neural cell adhesion molecule-associated polysialic acid inhibits NR2B-containing N-methyl-D-aspartate receptors and prevents glutamate-induced cell death. J Biol Chem 281:34859-34869
52. Kambara Y, Shiba K, Yoshida M, Sato C, Kitajima K, Shingyoji C (2011) Mechanism regulating Ca2+-dependent mechanosensory behaviour in sea urchin spermatozoa. Cell Struct Funct 36:69-82
53. Sato C, Kitajima K (1999) Glycobiology of di- and oligosialyl glycotopes. Trends Glycosci Glycotechnol 11:371-390
54. Sato C (2004) Glycobiology of di- and oligosialyl glycotopes. Trends Glycosci Glycotechnol 16:331-344
55. Nadanaka S, Sato C, Kitajima K, Katagiri K, Irie S, Yamagata T (2001) Occurrence of oligosialic acids on integrin alpha-5 subunit and their involvement in cell adhesion to fibronectin. J Biol Chem 276:33657-33664
56. Sato C, Matsuda T, Kitajima K (2002) Neuronal differentiation-dependent expression of the disialic acid epitope on CD166 and its involvement in neurite formation in Neuro2A cells. J Biol Chem 277:45299-45305
57. Yasukawa Z, Sato C, Sano K, Ogawa H, Kitajima K (2006) Identification of disialic acidcontaining glycoproteins in mouse serum: a novel modification of immunoglobulin light chains, vitronectin, and plasminogen. Glycobiology 16:651-665
58. Miyata S, Yamakawa N, Toriyama M, Sato C, Kitajima K (2011) Co-expression of two distinct polysialic acids, α2,8- and α2,9-linked polymers of N-acetylneuraminic acid, in distinct glycoproteins and glycolipids in sea urchin sperm. Glycobiology 21:1596-1605
59. Aminoff D (1961) Methods for the quantitative estimation of N-acetylneuraminic acid and their application to hydrolysates of sialomucoids. Biochem J 81:384-392
60. Uchida Y, Tsukada Y, Sugimori T (1977) Distribution of neuraminidase in Arthrobacter and its purification by affinity chromatography. J Biochem (Tokyo) 82:1425-1433
61. Svennerholm L (1957) Quantitative estimation of sialic acids. II. A colorimetric resorcinolhydrochloric acid method. Biochim Biophys Acta 24:604-611
62. Hara S, Takemori Y, Yamaguchi M, Nakamura M, Ohkura Y (1987) Fluorometric highperformance liquid chromatography of N-acetyl- and N-glycolylneuraminic acids and its application to their microdetermination in human and animal sera, glycoproteins, and glycolipids. Anal Biochem 164:138-145
63. Hara S, Yamaguchi M, Takemori Y, Furuhata K, Ogura H, Nakamura M (1989) Determination of mono-O-acetylated N-acetylneuraminic acids in human and rat sera by fluorometric high-performance liquid chromatography. Anal Biochem 179:162-166
64. Yamakawa N, Sato C, Miyata S, Maehashi E, Toriyama M, Sato N, Furuhata K, Kitajima K (2007) Development of sensitive chemical and immunochemical methods for detecting sulfated sialic acids and their application to glycoconjugates from sea urchin sperm and eggs. Biochimie 89:1396-1408
65. Kamerling JP, Schauer R, Shukla AK, Stoll S, Van Halbeek H, Vliegenthart JF (1987) Migration of O-acetyl groups in N, O-acetylneuraminic acids. Eur J Biochem 162:601-607
66. Finne J, Krusius T, Rauvala H (1977) Occurrence of disialosyl groups in glycoproteins. Biochem Biophys Res Commun 74:405-410
67. Michon F, Brisson JR, Jennings HJ (1987) Conformational differences between linear α2,8- linked homosialooligosaccharides and the epitope of the group B meningococcal polysaccharide. Biochemistry 26:8399-8405
68. Sato C, Kitajima K, Tazawa I, Inoue Y, Inoue S, Troy FA II (1993) Structural diversity in the α2-8-linked polysialic acid chains in salmonid fish egg glycoproteins. Occurrence of poly (Neu5Ac), poly(Neu5Gc), poly(Neu5Ac, Neu5Gc), poly(KDN), and their partially acetylated forms. J Biol Chem 268:23675-23684
69. Sato C, Inoue S, Matsuda T, Kitajima K (1998) Development of a highly sensitive chemical method for detecting α2,8-linked oligo/polysialic acid residues in glycoproteins blotted on the membrane. Anal Biochem 261:191-197
70. Sato C, Inoue S, Matsuda T, Kitajima K (1999) Fluorescent-assisted detection of oligosialyl units in glycoconjugates. Anal Biochem 266:102-109
71. Zhang Y, Lee YC (1999) Acid-catalyzed lactonization of α2,8-linked oligo/polysialic acids studied by high performance anion-exchange chromatography. J Biol Chem 274:6183-6189
72. Nakata D, Troy FA II (2005) Degree of polymerization (DP) of polysialic acid (polySia) on neural cell adhesion molecules (N-CAMS): development and application of a new strategy to accurately determine the DP of polySia chains on N-CAMS. J Biol Chem 275:38305-38316
73. Inoue S, Lin SL, Lee YC, Inoue Y (2001) An ultrasensitive chemical method for polysialic acid analysis. Glycobiology 11:759-767
74. Rohr TE, Troy FA (1980) Structure and biosynthesis of surface polymers containing polysialic acid in Escherichia coli. J Biol Chem 255:2332-2342
75. Kitajima K, Kuroyanagi H, Inoue S, Ye J, Troy FA 2nd, Inoue Y (1994) Discovery of a new type of sialidase, "KDNase," which specifically hydrolyzes deaminoneuraminyl (3-deoxy-Dglycero- D-galacto-2-nonulosonic acid) but not N-acylneuraminyl linkages. J Biol Chem 269:21415-21419
76. Kanamori A, Inoue S, Xulei Z, Zuber C, Roth J, Kitajima K, Ye J, Troy FA 2nd, Inoue Y (1994) Monoclonal antibody specific for α2,8-linked oligo deaminated neuraminic acid (KDN) sequences in glycoproteins. Preparation and characterization of a monoclonal antibody and its application in immunohistochemistry. Histochemistry 101:333-340
77. Song Y, Kitajima K, Inoue Y (1993) Monoclonal antibody specific to α2,3-linked deaminated neuraminyl beta-galactosyl sequence. Glycobiology 3:31-36
78. Angata T, Matsuda T, Kitajima K (1998) Synthesis of neoglycoconjugates containing deaminated neuraminic acid (KDN) using rat liver α2,6-sialyltransferase. Glycobiology 8:277-284
79. Ohta K, Sato C, Matsuda T, Toriyama M, Lennarz WJ, Kitajima K (1999) Isolation and characterization of low density detergent-insoluble membrane (LD-DIM) fraction from sea urchin sperm. Biochem Biophys Res Commun 258:616-623
80. Sarff LD, McCracken G, Schiffer MS, Glode MP, Robbins JB, Ørskov I, Ørskov F (1975) Epidemiology of Escherichia coli K1 in healthy and diseased newborns. Lancet 1975:1099-1104
81. Frosch M, Gorge I, Boulnois GJ, Timmis KN, Bitter-Suremann D (1985) NZB mouse system for production of monoclonal antibodies to weak bacterial antigens: isolation of an IgG antibody to the polysaccharide capsules of Escherichia coli K1 and group B meningococci. Proc Natl Acad Sci USA 82:194-1198
82. Jennings HJ, Roy R, Michon F (1985) Determinant specificities of the groups B and C polysaccharides of Neisseria meningitidis. J Immunol 134:2651-2657
83. Häyrinen J, Bitter-Suermann D, Finne J (1989) Interaction of meningococcal group B monoclonal antibody and its Fab fragment with α2-8-linked sialic acid polymers: requirement of a long oligosaccharide segment for binding. Mol Immunol 26:523-529
84. Sato C, Kitajima K, Inoue S, Seki T, Troy FA II, Inoue Y (1995) Characterization of the antigenic specificity of four different anti-(α2,8-linked polysialic acid) antibodies using lipid-conjugated oligo/polysialic acids. J Biol Chem 270:8923-18928
85. Sato C, Fukuoka H, Ohta K, Matsuda T, Koshino R, Kobayashi K, Troy FA II, Kitajima K (2000) Frequent occurrence of pre-existing α2!8-linked disialic and oligosialic acids with chain lengths up to 7 Sia residues in mammalian brain glycoproteins. Prevalence revealed by highly sensitive chemical methods and anti-di-, oligo-, and poly-Sia antibodies specific for defined chain lengths. J Biol Chem 275:15422-15431
86. Inoko E, Nishiura Y, Tanaka H, Takahashi T, Furukawa K, Kitajima K, Sato C (2010) Developmental stage-dependent expression of an α2,8-trisialic acid unit on glycoproteins in mouse brain. Glycobiology 20:916-928
87. Yasukawa Z, Sato C, Kitajima K (2007) Identification of an inflammation-inducible serum protein recognized by anti-disialic acid antibodies as carbonic anhydrase II. J Biochem 141:429-441
88. Jakobsson E, Schwarzer D, Jokilammi A, Finne J (2012) Endosialidases-versatile tools for the study ofpolysialic acid. Top Curr Chem. doi:10.1007/128_2012_349
89. Hallenbeck PC, Vimer ER, Yu F, Basseler B, Troy FA (1987) Purification and properties of a bacteriophage-induced endo-N-acetylneuraminidase specific for poly-α-2,8-sialosyl carbohydrate units. J Biol Chem 262:3553-3561
90. Pelkonen S, Perkonen J, Finne J (1989) Common cleavage pattern of polysialic acid by bacteriophage endosialidases of different properties and origins. J Virol 63:4409-4416
91. Miyake K, Muraki T, Hattori K, Machida Y, Watanabe M, Kawase M, Yoshida Y, Iijima S (1997) Screening of bacteriophages producing endo-N-acetylneuraminidase. J Ferm Bioeng 84:90-93
92. Aalto J, Pelkonen S, Kalimo H, Finne J (2001) Mutant bacteriophage with non-catalytic endosialidase binds to both bacterial and eukaryotic polysialic acid and can be used as probe for its detection. Glycoconj J 18:751-758
93. Martin LT, Marth JD, Varki A, Varki NM (2002) Genetically altered mice with different sialyltransferase deficiencies show tissue-specific alterations in sialylation and sialic acid 9-O-acetylation. J Biol Chem 277:32930-32982
94. Yamamoto K, Konami Y, Irimura T (1997) Sialic acid-binding motif of Maackia amurensis lectins. J Biochem 121:756-761
95. Kim BS, Oh TK, Cho DH, Kim YJ, Koo WM, Kong KH, Kom H (2004) A sialic-acid binding lectin from the legume Maackia fauriei: comparison with lectisn from M. amurensis. Plant Sci 167:1315-1321
96. Brinkmann-van der Linden ECM, Sonnenburg JL, Varki A (2002) Effects of sialic acid substitutions on recognition by Sambucus nigra agglutinin and Maackia amurensis Hemagglutinin. Anal Biochem 303:98-104
97. Nicholls JM, Bourne AJ, Chen H, Guan Y, Malik Peiris JS (2007) Sialic acid receptor detection in the human respiratory tract: evidence for widespread distribution of potential binding sites for human and avian influenza viruses. Respir Res 8:73-83
98. Imberty A, Gautier C, Lescar J, Perez S, Wyns L, Loris R (2000) An unusual carbohydrate binding site revealed by the structures of two Maackia amurensis lectins complexed with sialic acid-containing oligosaccharides. J Biol Chem 275:17541-17548
99. Geisler C, Jarvis DL (2011) Effective glycoanalysis with Maackia amurensis lectins requires a clear understanding of their binding specificities. Glycobiology 21:988-993
100. Herrler G, Rott R, Klenk HD, Muller HP, Shukla AK, Schauer R (1985) The receptordestroying enzyme of influenza C virus is neuraminate O-acetylesterase. EMBO J 4:1503-1506
101. Vlasak R, Krystal M, Nacht M, Palese P (1987) The influenza c virus glycoprotein (HE) exhibits receptor-binding (hemagglutinin) and receptor-destroying (esterase) activities. Virology 160:419-425
102. Zimmer G, Reuter G, Schauer R (1992) Use of influenza C virus for detection of 9-Oacetylated sialic acids on immobilized glycoconjugates by esterase activity. Eur J Biochem 204:209-215
103. Klein A, Krishna M, Varki NM, Varki A (1994) 9-O-Acetylated sialic acids have widespread but selective expression: analysis using a chimeric dual-function probe derived from influenza C hemagglutinin-esterase. Proc Natl Acad Sci USA 91:7782-7786
104. Shi WX, Chammas R, Varki NM, Powell L, Varki A (1996) Sialic acid 9-O-acetylation on murine erythroleukemia cells affects complement activation, binding to I-type lectins, and tissue homing. J Biol Chem 271:31526-31532
105. Muchmore E, Varki A (1987) Selective inactivation of influenza C esterase: a probe for detecting 9-O-acetylated sialic acids. Science 236:1293-1295
106. Mehansho H, Carlson DM (1983) Induction of protein and glycoprotein synthesis in rat submandibular glands by isoproterenol. J Biol Chem 258:6616-6620
107. Schwegmann-Webels C, Herrier G (2006) Sialic acids as receptor determinants for coronaviruses. Glycoconj J 23:51-58
108. Langereis MA, van Vliet ALW, Boot W, deGroot RJ (2010) Attachment of mouse hepatitis virus to O-acetylated sialic acid is mediated by hemaglutinin-esterase and not by the spike protein. J Virol 2010:8970-8974
109. Schauer R (1982) Sialic acids: chemistry, metabolism and function, cell biology monographs, vol 10. Springer, Berlin
110. Tangvoranuntakul P, Gagneux P, Diaz S, Bardor M, Varki N, Varki A, Muchmore E (2003) Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid. Proc Natl Acad Sci USA 100:12045-12050
111. Diaz SL, Padler-Karavani V, Ghaderi D, Hurtado-Ziola N, Yu H, Chen X, Brinkman-Van der Linden EC, Varki A, Varki NM (2009) Sensitive and specific detection of the non-human sialic acid N-glycolyneuraminic acid in human tissues and biotherapeutic products. PLoS One 4:e4241