Preparation of legionaminic acid analogs of sialo-glycoconjugates by means of mammalian sialyltransferases. 2015

David C Watson, and Warren W Wakarchuk, and Christian Gervais, and Yves Durocher, and Anna Robotham, and Steve M Fernandes, and Ronald L Schnaar, and N Martin Young, and Michel Gilbert
Human Health Therapeutics, National Research Council Canada, 100 Sussex Drive, Ottawa, ON, K1A 0R6, Canada.

Legionaminic acids are analogs of sialic acid that occur in several bacteria. The most commonly occurring form is Leg5Ac7Ac, which differs from Neu5Ac only at the C7 (acetamido) and C9 (deoxy) positions. While these differences greatly reduce the susceptibility of Leg compounds to sialidases, several sialyltransferases have been identified that can use CMP-Leg5Ac7Ac as a donor (Watson et al. 2011). We report the successful modification with Leg5Ac7Ac of a glycolipid, GM1a, and two glycoproteins, interferon-α2b and α1-antitrypsin, by means of two mammalian sialyltransferases, namely porcine ST3Gal1 and human ST6Gal1. The Leg5Ac7Ac form of GD1a was not recognized by the myelin-associated glycoprotein (MAG, Siglec-4), confirming the importance of the glycerol moiety in the interaction of sialo-glycans with Siglecs.

UI MeSH Term Description Entries
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D005677 G(M1) Ganglioside A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis. GM1 Ganglioside,Monosialosyl Tetraglycosyl Ceramide,GM1a Monosialoganglioside,Ceramide, Monosialosyl Tetraglycosyl,Ganglioside, GM1,Monosialoganglioside, GM1a,Tetraglycosyl Ceramide, Monosialosyl
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000515 alpha 1-Antitrypsin Plasma glycoprotein member of the serpin superfamily which inhibits TRYPSIN; NEUTROPHIL ELASTASE; and other PROTEOLYTIC ENZYMES. Trypsin Inhibitor, alpha 1-Antitrypsin,alpha 1-Protease Inhibitor,alpha 1-Proteinase Inhibitor,A1PI,Prolastin,Serpin A1,Zemaira,alpha 1 Antiprotease,alpha 1-Antiproteinase,1-Antiproteinase, alpha,Antiprotease, alpha 1,Inhibitor, alpha 1-Protease,Inhibitor, alpha 1-Proteinase,Trypsin Inhibitor, alpha 1 Antitrypsin,alpha 1 Antiproteinase,alpha 1 Antitrypsin,alpha 1 Protease Inhibitor,alpha 1 Proteinase Inhibitor
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D012794 Sialic Acids A group of naturally occurring N-and O-acyl derivatives of the deoxyamino sugar neuraminic acid. They are ubiquitously distributed in many tissues. N-Acetylneuraminic Acids,Acids, N-Acetylneuraminic,Acids, Sialic,N Acetylneuraminic Acids
D012799 Sialyltransferases A group of enzymes with the general activity CMP-N-acetylneuraminate:acceptor N-acetylneuraminyl transferase. They catalyze the transfer of N-ACETYLNEURAMINIC ACID from CMP-N-ACETYLNEURAMINIC ACID to an acceptor, which is usually the terminal sugar residue of an oligosaccharide, a glycoprotein, or a glycolipid. Glycoprotein Sialyltransferases,Glycosyltransferase Family 29,Sialyltransferase,Ectosialyltransferase,Glycoprotein Sialyltransferase,Sialyltransferase, Glycoprotein,Sialyltransferases, Glycoprotein
D013552 Swine Any of various animals that constitute the family Suidae and comprise stout-bodied, short-legged omnivorous mammals with thick skin, usually covered with coarse bristles, a rather long mobile snout, and small tail. Included are the genera Babyrousa, Phacochoerus (wart hogs), and Sus, the latter containing the domestic pig (see SUS SCROFA). Phacochoerus,Pigs,Suidae,Warthogs,Wart Hogs,Hog, Wart,Hogs, Wart,Wart Hog
D016898 Interferon-alpha One of the type I interferons produced by peripheral blood leukocytes or lymphoblastoid cells. In addition to antiviral activity, it activates NATURAL KILLER CELLS and B-LYMPHOCYTES, and down-regulates VASCULAR ENDOTHELIAL GROWTH FACTOR expression through PI-3 KINASE and MAPK KINASES signaling pathways. Interferon Alfa,Interferon, Leukocyte,Interferon, Lymphoblast,alpha-Interferon,IFN-alpha D,IFN-alpha5,Interferon alpha-1,Interferon alpha-17,Interferon alpha-4,Interferon alpha-5,Interferon alpha-7,Interferon alpha-88,Interferon alpha-J,Interferon alpha-T,Interferon alpha4,Interferon alpha5,Interferon, Lymphoblastoid,Interferon, alpha,LeIF I,LeIF J,Leif D,IFN alpha D,IFN alpha5,Interferon alpha,Interferon alpha 1,Interferon alpha 17,Interferon alpha 4,Interferon alpha 5,Interferon alpha 7,Interferon alpha 88,Interferon alpha J,Interferon alpha T,Leukocyte Interferon,Lymphoblast Interferon,Lymphoblastoid Interferon,alpha Interferon
D018992 Myelin-Associated Glycoprotein A myelin protein found in the periaxonal membrane of both the central and peripheral nervous systems myelin sheaths. It binds to cells surface receptors found on AXONS and may regulate cellular interactions between MYELIN and AXONS. Large Myelin-Associated Glycoprotein Isoform,Sialic Acid Binding Ig-Like Lectin 4A,Sialic Acid Binding Ig-like Lectin 4,Siglec-4,Small Myelin-Associated Glycoprotein Isoform,Large Myelin Associated Glycoprotein Isoform,Myelin Associated Glycoprotein,Sialic Acid Binding Ig Like Lectin 4A,Sialic Acid Binding Ig like Lectin 4,Siglec 4,Small Myelin Associated Glycoprotein Isoform

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