CMP substitutions preferentially inhibit polysialic acid synthesis

Glycobiology

Volumn 18, Issue 2, 2008, Pages 187-194

  Miyazaki, Tatsuo ^a,b   Angata, Kiyohiko ^a   Seeberger, Peter H ^a   Hindsgaul, Ole ^a   Fukuda, Minoru ^a  

^a BURNHAM INSTITUTE   (United States)

^b NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

2,8 sialyltransferase; 2 O methyl CMP; 5 methyl CMP; Polysialic acid

Indexed keywords

ALPHA 2,3 SIALYLTRANSFERASE; ALPHA 2,6 SIALYLTRANSFERASE; ALPHA 2,8 SIALYLTRANSFERASE; CYTIDINE PHOSPHATE; N BUTYLNEURAMINIC ACID; NEURAMINIC ACID; POLYSIALIC ACID; POLYSIALYLTRANSFERASE; SIALYLTRANSFERASE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; CARBOHYDRATE SYNTHESIS; CHINESE HAMSTER; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME GLYCOSYLATION; ENZYME INHIBITION; FEMALE; FETUS; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN METHYLATION;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; CYTIDINE MONOPHOSPHATE; FLOW CYTOMETRY; RATS; RECOMBINANT PROTEINS; SIALIC ACIDS; SIALYLTRANSFERASES;

CRICETULUS GRISEUS;

EID: 38649098777     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwm132     Document Type: Article

References (39)

1. Angata K, Fukuda M. 2005. Carbohydrates of neural cell glycoproteins: Structure, biosynthesis and function. In: Fukuda M, Rutishauser U, Schnaar RL, editors. Neuroglycobioloy. Oxford: Oxford University Press. p. 1-38.
2. Angata K, Huckaby V, Ranscht B, Terskikh A, Marth JD, Fukuda M. 2007. Polysialic acid-directed migration and differentiation of neural precursors is essential for mouse brain development. Mol Cell Biol. 27:6659-6668.
3. Angata K, Suzuki M, Fukuda M. 1998. Differential and cooperative polysialylation of the neural cell adhesion molecule by two polysialyltransferases; PST and STX. J Biol Chem. 273:28524-28532.
4. Angata K, Suzuki M, McAuliffe J, Ding Y, Hindsgaul O, Fukuda M. 2000. Differential biosynthesis of polysialic acid on neural cell adhesion moledule (NCAM) and oligosaccharide acceptors by three distinct α2,8-sialyltransferases, ST8Sia IV (PST), ST8Sia II (STX), and SI8Sia III. J Biol Chem. 275:18594-18601.
5. Angata K, Yen TY, El-Battari A, Macher BA, Fukuda M. 2001. Unique disulfide bond structures found in ST8Sia IV polysialyltransferase are required for its activity. J Biol Chem. 276:15369-15377.
6. Beres J, Bentrude WG, Otvos L, Balzarini J, De Clercq E. 1989. Synthesis and cytostatic and antiviral activities of 1-beta-D-ribofuranosyl-5-alkylcytosine (5-alkylcytidiae) cyclic 3′,5′ -monophosphates. J Med Chem. 32:224-228.
7. Close BE, Colley KJ. 1998. In vivo autopolysialylation and localization of the polysialyltransferases PST and STX. J Biol Chem. 273:34586-34593.
8. Datta AK, Paulson JC. 1995. The sialyltransferase "sialylmotif" participates in binding the donor substrate CMP-NeuAc. J Biol Chem. 270:1497-1500.
9. Datta AK, Sinha A, Paulson JC. 1998. Mutation of the sialyltransferase S-sialylmotif alters the kinetics of the donor and acceptor substrates. J Biol Chem. 273:9608-9614.
10. Eckhardt M, Muhlenhoff M, Bethe A, Koopman J. Frosch M. Gerardy-Schahn R. 1995. Molecular characterization of eukaryotic polysialyltransferase-1. Nature. 373:715-718.
11. Field RA, Otter A, Fu W, Hindsgaul O. 1995. Synthesis and 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O beta-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-beta-D-glucopyran oside. Carbohydr Res. 276:347-363.
12. Freeze HH. 2006. Genetic defects in the human glycome. Nat Rev Genet. 7:537-551.
13. Gross HJ, Merling A, Moldenhauer G, Schwartz-Albiez R. 1996. Ectosialyltransferase of human B lymphocytes reconstitutes differentiation markers in the presence of exogenous CMP-N-acetyl neuraminic acid. Blood. 87:5113-5126.
14. Harvey BE, Thomas P. 1993. Inhibition of CMP-sialic acid transport in human liver and colorectal cancer cell lines by a sialic acid nucleoside conjugate (KI-8110). Biochem Biophys Res Commun. 100:571-575.
15. Kijima-Suda I, Miyamoto Y, Toyoshima S, Itoh M, Osawa T. 1986. Inhibition of experimental pulmonary metastasis of mouse colon adenocarcinoma 26 sublines by a sialic acid: Nucleoside conjugate having sialyltransferase inhibiting activity. Cancer Res. 46:858-862.
16. Kijima-Suda, I, Miyazawa T, Itoh M, Toyoshima S, Osawa T. 1988. Possible mechanism of inhibition of experimental pulmonary metastasis of mouse colon adenocarcinoma 26 sublines by a sialic acid: Nucleoside conjugate. Cancer Res. 48:3728-3732.
17. Kleineidam RG, Schmelter T, Schwarz RT, Schauer R. 1997. Studies on the inhibition of sialyl- and galactosyltransferases. Glycoconj J. 14:57-66.
18. Mahal LK, Charter NW, Angata K, Fukuda M, Koshland DE Jr, Betozzi CR. 2001. A small-molecule modulator of poly-alpha 2,8-sialic acid expression on cultured neurons and tumor cells. Science. 294:380-381.
19. Martinez-Duncker I, Dupre T, Piller V, Piller F, Candelier JJ, Trichet C, Tchernia G, Oriol R, Mollicone R. 2005. Genetic complementation reveals a novel human congenital disorder of glycosylation of type II, due to inactivation of the Golgi CMP-sialic acid transporter. Blood. 105:2671-2676.
20. Nakayama J, Fukuda M. 1996. A human polysialyltransferase directs in vitro synthesis of polysialic acid. J Biol Chem. 271:1829-1832.
21. Nakayama J, Fukuda MN, Fredette B, Ranscht B, Fukuda M. 1995. Expression cloning of a human polysialyltransferase that forms the polysialylated neural cell adhesion molecule present in embryonic brain. Proc Natl Acad Sci USA. 92:7031-7035.
22. Palcic MM, Heerze LD, Pierce M, Hindsgaul O. 1988. The use of hydrophobic synthetic glycosides as acceptors in glycosyltransferase assays. Glycoconj J. 5:49-63.
23. Prescher JA, Dube DH, Bertozzi CR. 2004. Chemical remodelling of cell surfaces in living animals. Nature. 430:873-877.
24. Rabuka D, Hubbard SC, Laughlin ST, Argade SP, Bertozzi CR. 2006. A chemical reporter strategy to probe glycoprotein fucosylation. J Am Chem Soc. 128:12078-12079.
25. Sasaki H, Bothner B, Dell A, Fukuda M. 1987. Carbohydrate structure of erythropoietin expressed in Chinese hamster ovary cells by a human erythropoietin cDNA. J Biol Chem. 262:12059-12076.
26. Sasaki K, Watanabe E, Kawashima K, Sekine S, Dohi T, Oshima M, Hanai N, Nishi T, Hasegawa M. 1993. Expression cloning of a novel Gal beta (1-3/ 1-4) GlcNAc α2,3-sialyltransferase using lectin resistance selection. J Biol Chem. 268:22782-22787.
27. Sawa M, Hsu TL, Itoh T, Sugiyama M, Hanson SR, Vogt PK, Wong CH. 2006. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc Natl Acad Sci USA. 103:12371-12376.
28. Schauer R. 1982. Chemistry, metabolism, and biological functions of sialic acids. Adv Carbohydr Chem Biochem. 40:131-234.
29. Scheidegger EP, Lackie PM, Papay J, Roth J. 1994. In vitro and in vivo growth of clonal sublines of human small cell lung carcinoma is modulated by polysialic acid of the neural cell adhesion molecule. Lab Invest. 70:95-106.
30. Suzuki M, Suzuki M, Nakayama J, Suzuki A, Angata K, Chen S, Sakai K, Hagihara K, Yamaguchi Y, Fukuda M. 2005. Polysialic acid facilitates tumor invasion by glioma cells. Glycobiology. 15:887-894.
31. Tanaka M, Lee K, Martinez-Augustin O, He Y, Sanderson IR, Walker WA. 1996. Exogenous nucleotides alter the proliferation, differentiation and apoptosis of human small intestinal epithelium. J Nutr. 126:424-433.
32. Tsuboi S, Isogai Y, Hada N, King JK, Hindsgaul O, Fukuda M. 1996. 6′-Sulfo sialyl Lex but not 6-sulfo sialyl Lex expressed on the cell surface supports L-selectin-mediated adhesion. J Biol Chem. 271:27213-27216.
33. Varki A. 1992. Diversity in the sialic acids. Glycobiology. 2:25-40.
34. Wang WC, Cummings RD. 1988. The immobilized leukoagglutinin from the seeds of Maackia amurensis binds with high affinity to complex-type Asn-linked oligosaccharides containing terminal sialic acid-linked α2,3 to penultimate galactose residues. J Biol Chem. 263:4576-4585.
35. Weinhold B, Seidenfaden R, Rockle I, Muhlenhoff M, Schertzinger F, Conzelmann S, Marth JD, Gerardy-Schahn R, Hildebrandt H. 2005. Genetic ablation of polysialic acid causes severe neurodevelopmental defects rescued by deletion of the neural cell adhesion molecule. J Biol Chem. 280:42971-42977.
36. Weinstein J, Lee EU, McEntee K, Lai PH, Paulson JC. 1987. Primary structure of β-galactoside α2,6-sialyltransferase. Conversion of membrane-bound enzyme to soluble forms by cleavage of the NH2-terminal signal anchor. J Biol Chem. 262:17735-17743.
37. Wen DX, Livingston BD, Medzihradszky KF, Kelm S, Burlingame AL, Paulson JC. 1992. Primary structure of Galb1,3(4)GlcNAc α2,3-sialytransferase determined by mass spectrometry sequence analysis and molecular cloning. Evidence for a protein motif in the sialyltransferase gene family. J Biol Chem. 267:21011-21019.
38. Willig TB, Breton-Gorius J, Elbim C, Mignotte V, Kaplan C, Mollicone R, Pasquier C, Filipe A, Mielot F, Cartron JP et al. 2001. Macrothrombocytopenia with abnormal demarcation membranes in megakaryocytes and neutropenia with a complete lack of sialyl-Lewis-X antigen in leukocytes- a new syndrome? Blood. 97:826-828.
39. Windfuhr M, Manegold A, Muhlenhoff M, Eckhardt M, Gerardy-Schahn R. 2000. Molecular defects that cause loss of polysialic acid in the complementation group 2A10. J Biol Chem. 275:32861-32870.