Abstract
The cytidine monophosphate N-acetylneuraminic acid synthetase (CMAS) catalyzes the activation of the nine-carbon amino sugar N-acetylneuraminic acid (NeuAc) and other sialic acid (Sia) derivatives to the sugar nucleotide cytidine monophosphate N-acetylneuraminic acid (CMP-NeuAc or CMP-Sia) (Kean 1991) by the following reaction:
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References
Allen KN, Dunaway-Mariano D (2004) Phosphoryl group transfer: evolution of a catalytic scaffold. Trends Biochem Sci 29:495–503
Angata T, Varki A (2002) Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem Rev 102:439–469
Burroughs AM, Allen KN, Dunaway-Mariano D, Aravind L (2006) Evolutionary genomics of the HAD superfamily: understanding the structural adaptations and catalytic diversity in a superfamily of phosphoesterases and allied enzymes. J Mol Biol 361:1003–1034
Cohen M, Varki A (2010) The sialome–far more than the sum of its parts. OMICS 14:455–464
Comb DG, Watson DR, Roseman S (1966) The sialic acids. IX. Isolation of cytidine 5′-monophospho-N-acetylneuraminic acid from Escherichia coli K-235. J Biol Chem 241:5637–5642
Comb DG, Shimizu F, Roseman S (1959) Isolation of cytidine 5′-monophospho-N-acetylneuraminic acid. J Am Chem Soc 81:5513–5514
Emig S, Schmalz D, Shakibaei M, Buchner K (1995) The nuclear pore complex protein p62 is one of several sialic acid-containing proteins of the nuclear envelope. J Biol Chem 270:13787–13793
Fujita A, Sato C, Kitajima K (2007) Identification of the nuclear export signals that regulate the intracellular localization of the mouse CMP-sialic acid synthetase. Biochem Biophys Res Commun 355:174–180
Fujita A, Sato C, Münster-Kühnel AK, Gerardy-Schahn R, Kitajima K (2005) Development of a simple and efficient method for assaying cytidine monophosphate sialic acid synthetase activity using an enzymatic reduced nicotinamide adenine dinucleotide/oxidized nicotinamide adenine dinucleotide converting system. Anal Biochem 337:12–21
Ghalambor MA, Heath EC (1966) The biosynthesis of cell wall lipopolysaccharide in Escherichia coli. IV. Purification and properties of cytidine monophosphate 3-deoxy-d- manno-octulosonate synthetase. J Biol Chem 241:3216–3221
Gross HJ, Brossmer R (1987) N-Acetyl-4-deoxy-D-neuraminic Acid is activated and transferred on to Asialoglycoprotein. Glycoconj J 4:145–156
Gross HJ, Bunsch A, Paulson JC, Brossmer R (1987) Activation and transfer of novel synthetic 9-substituted sialic acids. Eur J Biochem 168:595–602
Haft RF, Wessels MR (1994) Characterization of CMP-N-acetylneuraminic acid synthetase of group B streptococci. J Bacteriol 176:7372–7374
Hinderlich S, Stäsche R, Zeitler R, Reutter W (1997) A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver. Purification and characterization of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase. J Biol Chem 272:24313–24318
Horsfall LE, Nelson A, Berry A (2010) Identification and characterization of important residues in the catalytic mechanism of CMP-Neu5Ac synthetase from Neisseria meningitidis. FEBS J 277:2779–2790
Kean EL (1969) Sialic acid activating enzyme in ocular tissue. Exp Eye Res 8:44–54
Kean EL (1970) Nuclear cytidine 5′-monophosphosialic acid synthetase. J Biol Chem 245:2301–2308
Kean EL (1991) Sialic acid activation. Glycobiology 1:441–447
Kean EL, Bighouse KJ (1974) Cytidine 5′-monophosphosialic acid hydrolase. Subcellular location and properties. J Biol Chem 249:7813–7823
Kean EL, Münster-Kühnel AK, Gerardy-Schahn R (2004) CMP-sialic acid synthetase of the nucleus. Biochimica et Biophysica Acta-General Subjects 1673:56–65
Kean EL, Roseman S (1966) The sialic acids. X. Purification and properties of cytidine 5′-monophosphosialic acid synthetase. J Biol Chem 241:5643–5650
Krapp S, Münster-Kühnel AK, Kaiser JT, Huber R, Tiralongo J, Gerardy-Schahn R, Jacob U (2003) The crystal structure of murine CMP-5-N-acetylneuraminic acid synthetase. J Mol Biol 334:625–637
Lawrence SM, Huddleston KA, Tomiya N, Nguyen N, Lee YC, Vann WF, Coleman TA, Betenbaugh MJ (2001) Cloning and expression of human sialic acid pathway genes to generate CMP-sialic acids in insect cells. Glycoconj J 18:205–213
Lewis AL, Cao H, Patel SK, Diaz S, Ryan W, Carlin AF, Thon V, Lewis WG, Varki A, Chen X, Nizet V (2007) NeuA sialic acid O-acetylesterase activity modulates O-acetylation of capsular polysaccharide in group B streptococcus. J Biol Chem 282:27562–27571
Mizanur RM, Pohl NL (2007) Cloning and characterization of a heat-stable CMP-N-acylneuraminic acid synthetase from clostridium thermocellum. Appl Microbiol Biotechnol 76:827–834
Mizanur RM, Pohl NL (2008) Bacterial CMP-sialic acid synthetases: production, properties, and applications. Appl Microbiol Biotechnol 80:757–765
Mosimann SC, Gilbert M, Dombroswki D, To R, Wakarchuk W, Strynadka NC (2001) Structure of a sialic acid-activating synthetase, CMP-acylneuraminate synthetase in the presence and absence of CDP. J Biol Chem 276:8190–8196
Münster AK, Eckhardt M, Potvin B, Mühlenhoff M, Stanley P, Gerardy-Schahn R (1998) Mammalian cytidine 5′-monophosphate N-acetylneuraminic acid synthetase: a nuclear protein with evolutionarily conserved structural motifs. Proc Natl Acad Sci U S A 95:9140–9145
Münster AK, Weinhold B, Gotza B, Mühlenhoff M, Frosch M, Gerardy-Schahn R (2002) Nuclear localization signal of murine CMP-Neu5Ac synthetase includes residues required for both nuclear targeting and enzymatic activity. J Biol Chem 277:19688–19696
Münster-Kühnel AK, Tiralongo J, Krapp S, Weinhold B, Ritz-Sedlacek V, Jacob U, Gerardy-Schahn R (2004) Structure and function of vertebrate CMP-sialic acid synthetases. Glycobiology 14:43R–51R
Nakata D, Münster AK, Gerardy-Schahn R, Aoki N, Matsuda T, Kitajima K (2001) Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N- acetylneuraminic acid (Neu5Ac) as substrates. Glycobiology 11:685–692
Oschlies M, Dickmanns A, Haselhorst T, Schaper W, Stummeyer K, Tiralongo J, Weinhold B, Gerardy-Schahn R, von Itzstein M, Ficner R, Münster-Kühnel AK (2009) A C-terminal phosphatase module conserved in vertebrate CMP-sialic acid synthetases provides a tetramerization interface for the physiologically active enzyme. J Mol Biol 393:83–97
Potvin B, Raju TS, Stanley P (1995) Lec32 is a new mutation in Chinese hamster ovary cells that essentially abrogates CMP-N-acetylneuraminic acid synthetase activity. J Biol Chem 270:30415–30421
Richard M, Martin A, Louisot P (1975) Evidence for glycosyl-transferases in rat liver nuclei. Biochem Biophys Res Commun 64:109–114
Rodriguez-Aparicio LB, Luengo JM, Gonzalez-Clemente C, Reglero A (1992) Purification and characterization of the nuclear cytidine 5′-monophosphate N-acetylneuraminic acid synthetase from rat liver. J Biol Chem 267:9257–9263
Roseman S (1962) Enzymatic synthesis of cytidine 5′-mono-phospho-sialic acids. Proc Natl Acad Sci U S A 48:437–441
Schaper W, Bentrop J, Ustinova J, Blume L, Kats E, Tiralongo J, Weinhold B, Bastmeyer M, Münster-Kühnel AK (2012) Identification and biochemical characterization of two functional CMP-sialic acid synthetases in Danio rerio. J Biol Chem 287:13239–13248
Schauer R, Haverkamp J, Ehrlich K (1980) Isolation and characterization of acylneuraminate cytidylyltransferase from frog liver. Hoppe Seylers Z Physiol Chem 361:641–648
Schwarzkopf M, Knobeloch KP, Rohde E, Hinderlich S, Wiechens N, Lucka L, Horak I, Reutter W, Horstkorte R (2002) Sialylation is essential for early development in mice. Proc Natl Acad Sci U S A 99:5267–5270
Shoyab M, Bachhawat BK (1967) Age dependent changes in the level of cytidine 5′-monophospho-N-acetyl neuraminic acid synthesizing and degrading enzymes and bound sialic acid in rat liver. Indian J Biochem 4:142–145
Shoyab M, Pattabiraman TN, Bachhawat BK (1964) Purification and properties of the CMP-N-acetylneuraminic acid synthesizing enzyme from sheep brain. J Neurochem 11:639–646
Steenbergen SM, Lee YC, Vann WF, Vionnet J, Wright LF, Vimr ER (2006) Separate pathways for O acetylation of polymeric and monomeric sialic acids and identification of sialyl O-acetyl esterase in Escherichia coli K1. J Bacteriol 188:6195–6206
Svennerholm L (1956) The quantitative estimation of cerebrosides in nervous tissue. J Neurochem 1:42–53
Terada T, Kitajima K, Inoue S, Koppert K, Brossmer R, Inoue Y (1996) Substrate specificity of rainbow trout testis CMP-3-deoxy-D-glycero-D-galacto-nonulosonic acid (CMP-Kdn) synthetase: kinetic studies of the reaction of natural and synthetic analogues of nonulosonic acid catalyzed by CMP-Kdn synthetase. Eur J Biochem 236:852–855
Terada T, Kitazume S, Kitajima K, Inoue S, Ito F, Troy FA, Inoue Y (1993) Synthesis of CMP-deaminoneuraminic acid (CMP-KDN) using the CTP: CMP-3- deoxynonulosonate cytidylyltransferase from rainbow trout testis. Identification and characterization of a CMP-KDN synthetase. J Biol Chem 268:2640–2648
Tiralongo J, Fujita A, Sato C, Kitajima K, Lehmann F, Oschlies M, Gerardy-Schahn R, Münster-Kühnel AK (2007) The rainbow trout CMP-sialic acid synthetase utilises a nuclear localization signal different from that identified in the mouse enzyme. Glycobiology 17:945–954
Van den Eijnden DH, Meems L, Roukema PA (1972) The regional distribution of cytidine 5′-monophospho-N-acetyl-neuraminic acid synthetase in calf brain. J Neurochem 19:1649–1658
van Dijk W, Ferwerda W, Van den Eijnden DH (1973) Subcellular and regional distribution of CMP-N-acetylneuraminic acid synthetase in the calf kidney. Biochim Biophys Acta 315:162–175
Vann WF, Silver RP, Abeijon C, Chang K, Aaronson W, Sutton A, Finn CW, Lindner W, Kotsatos M (1987) Purification, properties, and genetic location of Escherichia coli cytidine 5′-monophosphate N-acetylneuraminic acid synthetase. J Biol Chem 262:17556–17562
Varki NM, Varki A (2007) Diversity in cell surface sialic acid presentations: implications for biology and disease. Lab Invest 87:851–857
Vimr ER, Aaronson W, Silver RP (1989) Genetic analysis of chromosomal mutations in the polysialic acid gene cluster of Escherichia coli K1. J Bacteriol 171:1106–1117
Vionnet J, Concepcion N, Warner T, Zapata G, Hanover J, Vann WF (1999) Purification of CMP-N-acetylneuraminic acid synthetase from bovine anterior pituitary glands. Glycobiology 9:481–487
Viswanathan K, Tomiya N, Park J, Singh S, Lee YC, Palter K, Betenbaugh MJ (2006) Expression of a functional drosophila melanogaster CMP-sialic acid synthetase. Differential localization of the drosophila and human enzymes. J Biol Chem 281:15929–15940
Warren L (1959) The thiobarbituric acid assay of sialic acids. J Biol Chem 234:1971–1975
Warren L, Blacklow RS (1962) The biosynthesis of cytidine 5′-monophospho-n-acetylneuraminic acid by an enzyme from Neisseria meningitidis. J Biol Chem 237:3527–3534
Weinhold B, Sellmeier M, Schaper W, Blume L, Philippens B, Kats E, Bernard U, Galuska SP, Geyer H, Geyer R, Worthmann K, Schiffer M, Groos S, Gerardy-Schahn R, Münster-Kühnel AK (2012) Deficits in sialylation impair podocyte maturation. J Am Soc Nephrol 23:1319–1328
Yu H, Ryan W, Yu H, Chen X (2006) Characterization of a bifunctional cytidine 5′-monophosphate N-acetylneuraminic acid synthetase cloned from Streptococcus agalactiae. Biotechnol Lett 28:107–113
Zapata G, Vann WF, Aaronson W, Lewis MS, Moos M (1989) Sequence of the cloned Escherichia coli K1 CMP-N-acetylneuraminic acid synthetase gene. J Biol Chem 264:14769–14774
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Weinhold, B., Gerardy-Schahn, R., Münster-Kühnel, A. (2014). Cytidine Monophosphate N-Acetylneuraminic Acid Synthetase (CMAS). In: Taniguchi, N., Honke, K., Fukuda, M., Narimatsu, H., Yamaguchi, Y., Angata, T. (eds) Handbook of Glycosyltransferases and Related Genes. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54240-7_39
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