Kwasy sjalowe – budowa i właściwości

Jakub Iwaszczuk; Aneta Baj; Piotr Wałejko

doi:10.56782/pps.244

Published : 2024-10-21

Vol. 22 No. 4 (2024)

Sialic acids – structure and properties

Jakub Iwaszczuk

Aneta Baj

Piotr Wałejko

DOI: https://doi.org/10.56782/pps.244

Abstract

Sialic acids (SA), derivatives of neuraminic acid (Neu), are 9-carbon monosaccharides featuring a carboxyl group at the anomeric carbon atom C-2. The term "sialic acid", derived from the Greek word "σάλιο" (saliva), was proposed by Gunnar Blix in 1952 to describe the product of acid hydrolysis of salivary mucins. SA are crucial components of many glycoproteins, glycolipids, and glycopeptides. Key properties of SA include imparting a negative charge to glycoconjugates, polarizing cell membranes, modifying the macromolecular structure of certain glycoproteins, and influencing cellular recognition of low- and high-molecular-weight chemical compounds. The most prevalent SA are N-acetylneuraminic acid (Neu5Ac) and N-glycolylneuraminic acid (Neu5Gc). Neu5Ac is widely present, whereas Neu5Gc is absent in physiological human tissues due to a mutation in the gene encoding CMAH (cytidine monophosphate-N-acetylneuraminic acid hydroxylase), which is responsible for converting Neu5Ac to Neu5Gc. The absence of Neu5Gc in humans, resulting from the inactive form of CMAH, may have significant implications for the biological roles of SA in the human body. This review aims to explore the current literature on the multifaceted roles of sialic acids, particularly in the context of their impact on human health and disease. Special attention is given to the influence of dietary sialic acids on the correlation between their intake and cancer development. By summarizing recent findings, this review highlights potential carcinogenic effects of dietary sialic acids, based on the latest research data.

Keywords:

sialic acids, Neu5Ac, Neu5Gc, cancer biomarkers

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Iwaszczuk, J., Baj, A., & Wałejko, P. (2024). Sialic acids – structure and properties. Prospects in Pharmaceutical Sciences, 22(4), 31–38. https://doi.org/10.56782/pps.244

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References

Blix, G.; Svennerholm, L.; Werner, I.; Finsnes, E.; Sörensen, J.S.; Sörensen, N.A. The Isolation of Chondrosamine from Gangliosides and from Submaxillary Mucin. Acta Chem. Scand. 1952, 6, 358–362. DOI: 10.3891/acta.chem.scand.06-0358.

Blix, F.G.; Gottschalk, A.; Klenk, E. Proposed Nomenclature in the Field of Neuraminic and Sialic Acids. Nature 1957, 179(4569), Art. No: 1088. DOI: 10.1038/1791088b0

Essentials of Glycobiology — NCBI Bookshelf.

Available online: https://www.ncbi.nlm.nih.gov/

books/NBK579918 (accessed on 13 June 2024).

Lundblad, A. Gunnar Blix and His Discovery

of Sialic Acids. Fascinating Molecules in

Glycobiology. Ups. J. Med. Sci. 2015, 1–9. DOI: 10.3109/03009734.2015.1027429

Carter, A.; Martin, N.H. Serum Sialic Acid Levels in Health and Disease. J. Clin. Pathol. 1962, 15(1), 69–72. doi: 10.1136/jcp.15.1.69

Schauer, R.; Kamerling, J.P. Exploration of the Sialic Acid World. Adv. Carbohyd. Chem. Biochem., 2018, 75, 1–213. DOI: 10.1016/bs.accb.2018.09.001

Gottschalk, A. Structural Relationship between Sialic Acid, Neuraminic Acid and 2-Carboxy-Pyrrole. Nature 1955, 176(4488), 881–882. doi: 10.1038/176881a0

Von Itzstein, M.; Thomson, R.J. The Synthesis of Novel Sialic Acids as Biological Probes. In Glycoscience Synthesis of Oligosaccharides and Glycoconjugates; Driguez, H., Thiem, J., Eds.; Springer, Berlin, Heidelberg, 1997; Volume 186, pp. 119–170. doi: 10.1007/BFb0119222

Yang, H.; Lu, L.; Chen, X. An Overview and Future Prospects of Sialic Acids. Biotechnol. Adv. 2021, 46, Art. No: 107678. doi: 10.1016/j.biotechadv.2020.107678

McNaught, A.D. Nomenclature of Carbohydrates (IUPAC Recommendations 1996). Pure Appl. Chem. 1996, 68(10), 1919–2008. DOI: 10.1351/pac199668101919

Lewis, A.L.; Toukach, P.; Bolton, E. et al. Cataloging Natural Sialic Acids and Other Nonulosonic Acids (NulOs), and Their Representation Using the Symbol Nomenclature for Glycans. Glycobiology 2023, 33(2), 99–103. DOI: 10.1093/glycob/cwac072

Pradhan, K.; Kulkarni, S.S. Synthesis of Nonulosonic Acids. Eur. J. Org. Chem. 2020, 2020(44), 6819–6830. DOI: 10.1002/ejoc.202000250

Knirel, Y. A.; Vinogradov, E.V.; L’vov, V.L.; Kocharova, N.A.; Shashkov, A.S.; Dmitriev, B.A.; Kochetkov,

N.K. Sialic Acids of a New Type from the Lipopolysaccharides of Pseudomonas Aeruginosa and Shigella Boydii. Carbohydr. Res. 1984, 133(2), C5–C8. DOI: 10.1016/0008-6215(84)85213-1

Zamora, C.Y.; Schocker, N.S.; Chang, M.M.; Imperiali, B. Chemoenzymatic Synthesis and Applications of Prokaryote-Specific UDP-Sugars. In Methods in Enzymology; Elsevier, Amsterdam, Netherlands,

; Volume 597, pp. 145–186. DOI: 10.1016/bs.mie.2017.06.003

Varki, A. Biological Roles of Glycans. Glycobiology 2017, 27(1), 3–49. DOI: 10.1093/glycob/cww086

Lauc, G.; Pezer, M.; Rudan, I.; Campbell, H. Mechanisms of Disease: The Human N-Glycome. BBA – Gen. Sub. 2016, 1860(8), 1574–1582. DOI: 10.1016/j.bbagen.2015.10.016

Visser, E. A.; Moons, S.J.; Timmermans, S.B.P.E.; De Jong, H.; Boltje, T.J.; Büll, C. Sialic Acid O-Acetylation: From Biosynthesis to Roles in Health and Disease. J. Biol. Chem. 2021, 297(2), Art. No: 100906. DOI: 10.1016/j.jbc.2021.100906

Sumida, M.; Hane, M.; Yabe, U.; Shimoda, Y.; Pearce, O.M.T.; Kiso, M.; Miyagi, T.; Sawada, M.; Varki, A.; Kitajima, K.; Sato, C. Rapid Trimming of Cell Surface Polysialic Acid (PolySia) by Exovesicular Sialidase Triggers Release of Preexisting Surface Neurotrophin. J. Biol. Chem. 2015, 290(21), 13202–13214. DOI: 10.1074/jbc.M115.638759

Lombard, V.; Golaconda Ramulu, H.; Drula, E.; Coutinho, P.M.; Henrissat, B. The Carbohydrate-Active Enzymes Database (CAZy) in 2013. Nucleic Acids Res. 2014, 42(D1), D490–D495. DOI: 10.1093/nar/gkt1178

Ling, A.J.W.; Chang, L.S.; Babji, A.S.; Latip, J.; Koketsu, M.; Lim, S.J. Review of Sialic Acid’s Biochemistry, Sources, Extraction and Functions with Special Reference to Edible Bird’s Nest.

Food Chem. 2022, 367, Art. No: 130755. DOI: 10.1016/j.foodchem.2021.130755

Gottschalk, A. The Chemistry and Biology of Sialic Acids and Related Substances, University Press, Cambridge, England, 1960, pp. 12–44.

Kątnik−Prastowska, I. Struktura i biologia kwasów sjalowych, Adv. Clin. Exp. Med., 2003, 12(5), 653–663

Stencel-Baerenwald, J.E.; Reiss, K.; Reiter, D.M.; Stehle, T.; Dermody, T.S. The Sweet Spot: Defining Virus–Sialic Acid Interactions. Nat. Rev. Microbiol. 2014, 12(11), 739–749. DOI: 10.1038/nrmicro3346

Wasik, B.R.; Barnard, K.N.; Parrish, C.R. Effects of

Sialic Acid Modifications on Virus Binding and Infection. Trends Microbiol. 2016, 24(12), 991–1001. DOI: 10.1016/j.tim.2016.07.005

Varki, A.; Gagneux, P. Multifarious Roles of Sialic Acids in Immunity. Ann. N. Y. Acad. Sci. 2012, 1253(1), 16–36. DOI: 10.1111/j.1749-6632.2012.06517.x

Petridis, A.K.; El Maarouf, A.; Rutishauser, U. Polysialic Acid Regulates Cell Contact‐dependent Neuronal Differentiation of Progenitor Cells from the Subventricular Zone. Dev. Dyn. 2004, 230(4), 675–684. DOI: 10.1002/dvdy.20094

Kiss, J.Z.; Rougon, G. Cell Biology of Polysialic Acid. Curr. Opin. Neurobiol. 1997, 7(5), 640–646. DOI: 10.1016/S0959-4388(97)80083-9

Bode, L. Human Milk Oligosaccharides: Every Baby Needs a Sugar Mama. Glycobiology 2012, 22(9), 1147–1162. DOI: 10.1093/glycob/cws074

Corfield, T. Bacterial Sialidases — Roles in Pathogenicity and Nutrition. Glycobiology 1992, 2(6), 509–521. DOI: 10.1093/glycob/2.6.509

Chen, G.-Y.; Brown, N.K.; Wu, W.; Khedri, Z.; Yu, H.; Chen, X.; Van De Vlekkert, D.; D’Azzo, A.; Zheng, P.; Liu, Y. Broad and Direct Interaction between TLR and Siglec Families of Pattern Recognition Receptors and Its Regulation by Neu1. eLife 2014, 3, Art. No: e04066. DOI: 10.7554/eLife.04066

Heise, T.; Pijnenborg, J.F.A.; Büll, C.; Van Hilten, N.; Kers-Rebel, E.D.; Balneger, N.; Elferink, H.; Adema, G.J.; Boltje, T.J. Potent Metabolic Sialylation

Inhibitors Based on C-5-Modified Fluorinated Sialic Acids. J. Med. Chem. 2019, 62(2), 1014–1021. DOI: 10.1021/acs.jmedchem.8b01757

Heise, T.; Langereis, J.D.; Rossing, E.; De Jonge, M.I.; Adema, G.J.; Büll, C.; Boltje, T.J. Selective

Inhibition of Sialic Acid-Based Molecular Mimicry in Haemophilus Influenzae Abrogates Serum Resistance. Cell Chem. Biol. 2018, 25(10), 1279-1285. DOI: 10.1016/j.chembiol.2018.05.018

Ikeda, K.; Sano, K.; Ito, M.; Saito, M.; Hidari, K.; Suzuki, T.; Suzuki, Y.; Tanaka, K. Synthesis of 2-Deoxy-2,3-Didehydro-N-Acetylneuraminic Acid Analogues Modified at the C-4 and C-9 Positions and Their Behaviour towards Sialidase from Influenza Virus and Pig Liver Membrane. Carbohydr. Res. 2001, 330(1), 31–41. DOI: 10.1016/S0008-6215(00)00267-6

Von Itzstein, M.; Wu, W.-Y.; Kok, G.B.; Pegg, M.S.; Dyason, J.C.; Jin, B.; Van Phan, T.; Smythe, M.L.; White, H.F.; Oliver, S.W.; Colman, P.M.; Varghese, J.N.; Ryan, D.M.; Woods, J.M.; Bethell, R.C.; Hotham, V.J.; Cameron, J.M.; Penn, C.R. Rational Design of Potent Sialidase-Based Inhibitors of Influenza Virus Replication. Nature 1993, 363(6428), 418–423. DOI: 10.1038/363418a0

Chandler, M.; Bamford, M.J.; Conroy, R.; Lamont, B.; Patel, B.; Patel, V.K.; Steeples, I.P.; Storer, R.; Weir, N.G.; Wright, M.; Williamson, C. Synthesis of the Potent Influenza Neuraminidase Inhibitor 4-Guanidino Neu5Ac2en. X-Ray Molecular Structure of 5-Acetamido-4-Amino-2,6-Anhydro-3,4,5-Trideoxy-D-Erythro-L-Gluco-Nononic Acid. J. Chem. Soc. Perkin 1995, 1(9),

Art. No: 1173. DOI: 10.1039/p19950001173

Wang‐Jairaj, J.; Miller, I.; Joshi, A.; Jayabalan, T.; Peppercorn, A.; Zammit‐Tabona, P.; Oliver, A. Zanamivir Aqueous Solution in Severe Influenza: A Global Compassionate Use Program, 2009–2019. Influenza Other Respir. Viruses 2022, 16(3), 542–551. DOI: 10.1111/irv.12947

Schauer, R.; Srinivasan, G.V.; Wipfler, D.; Kniep, B.; Schwartz-Albiez, R. O-Acetylated Sialic Acids and Their Role in Immune Defense. In The Molecular Immunology of Complex Carbohydrates-3; Wu, A. M., Ed.; Springer, US, Boston, 2011; Volume 705, pp 525–548. DOI: 10.1007/978-1-4419-7877-6_28

Cheeseman, J.; Badia, C.; Elgood-Hunt, G.; Gardner, R. A.; Trinh, D.N.; Monopoli, M. P.; Kuhnle, G.; Spencer, D.I.R.; Osborn, H.M.I. Elevated Concentrations of Neu5Ac and Neu5,9Ac2 in Human Plasma: Potential Biomarkers of Cardiovascular Disease. Glycoconj. J. 2023, 40(6), 645–654. DOI: 10.1007/s10719-023-10138-3

Klein, A.; Diaz, S.; Ferreira, I.; Lamblin, G.; Roussel, P.; Manzi, A.E. New Sialic Acids from Biological

Sources Identified by a Comprehensive and Sensitive Approach: Liquid Chromatography-Electrospray Ionization-Mass Spectrometry (LC-ESI-MS) of SIA Quinoxalinones. Glycobiology 1997, 7(3), 421–432. DOI: 10.1093/glycob/7.3.421

Schauer, R. Sialic Acids: Fascinating Sugars in Higher Animals and Man. Zoology 2004, 107(1), 49–64. DOI: 10.1016/j.zool.2003.10.002

Huang, X.; Li, Z.; Xiaobo, Z.; Shi, J.; Tahir, H.E.; Xu, Y.; Zhai, X.; Hu, X. Geographical Origin Discrimination of Edible Bird’s Nests Using Smart Handheld Device Based on Colorimetric Sensor Array. J. Food Meas. Charact. 2020, 14(1), 514–526. DOI: 10.1007/s11694-019-00251-z

Ling, J.W.A.; Chang, L.S.; Babji, A.S.; Lim, S.J. Recovery of Value‐added Glycopeptides from Edible Bird’s Nest (EBN) Co‐products: Enzymatic Hydrolysis, Physicochemical Characteristics and Bioactivity. J.

Sci. Food Agric. 2020, 100(13), 4714–4722. DOI: 10.1002/jsfa.10530

Wang, H.-J.; Hua, C.-Z.; Ruan, L.-L.; Hong, L.-Q.; Sheng, S.-Q.; Shang, S.-Q. Sialic Acid and Iron Content

in Breastmilk of Chinese Lactating Women. Indian Pediatr. 2017, 54(12), 1029–1031. DOI: 10.1007/s13312-017-1206-z

Juneja, L.R.; Koketsu, M.; Nishimoto, K.; Kim, M.; Yamamoto, T.; Itoh, T. Large-Scale Preparation of Sialic Acid from Chalaza and Egg-Yolk Membrane. Carbohydr. Res. 1991, 214(1), 179–186. DOI: 10.1016/S0008-6215(00)90540-8

Koketsu, M.; Juneja, L.R.; Kawanami, H.; Kim, M.; Yamamoto, T. Preparation of N-Acetylneuraminic Acid from Delipidated Egg Yolk. Glycoconj. J. 1992, 9(2), 70–74. DOI: 10.1007/BF00731701

Sun, X.; Gänzle, M.; Field, C.J.; Wu, J. Effect of Proteolysis on the Sialic Acid Content and Bifidogenic Activity of Ovomucin Hydrolysates. Food Chem. 2016, 212, 78–86. DOI: 10.1016/j.foodchem.2016.05.153

Tang, K.-T.; Liang, L.-N.; Cai, Y.-Q.; Mou, S.-F. Determination of Sialic Acid in Milk and Products Using High Performance Anion-Exchange Chromatography Coupled with Pulsed Amperometric Detection. Chin.

J. Anal. Chem. 2008, 36(11), 1535–1538. DOI: 10.1016/S1872-2040(09)60005-0

Wang, X.; Ma, T.; Yu, H.; Chen, Z.; Zhu, B.; Chen, W.; Sun, S.; Li, Z. Purification of Sialoglycoproteins from Bovine Milk Using Serotonin-Functionalized Magnetic Particles and Their Application against Influenza A

Virus. Food Funct. 2020, 11(8), 6911–6920. DOI: 10.1039/D0FO01447H

Suzuki, T.; Horiike, G.; Yamazaki, Y.; Kawabe, K.; Masuda, H.; Miyamoto, D.; Matsuda, M.; Nishimura, S.-I.; Yamagata, T.; Ito, T.; Kida, H.; Kawaoka, Y.; Suzuki, Y. Swine Influenza Virus Strains Recognize Sialylsugar Chains Containing the Molecular Species of Sialic Acid Predominantly Present in the Swine Tracheal Epithelium. FEBS Lett. 1997, 404(2–3), 192–196. DOI: 10.1016/S0014-5793(97)00127-0

Sroga, J.M.; Wu, D.H.; Ma, F.; Tecle, E.; Ressler, I.B.; Maxwell, R.; Ferrari, R.; Whigham, L.; Gagneux, P.; Lindheim, S.R. Detection of the Dietary Xenoglycan N-Glycolylneuraminic Acid (Neu5Gc) and Anti-Neu5Gc Antibodies within Reproductive Tracts of Male and Female Infertility Subjects. Clin. Obstet. Gynecol. Reprod. Med. 2015, 1(3), 72–78. DOI: 10.15761/COGRM.1000120

Peri, S.; Kulkarni, A.; Feyertag, F.; Berninsone, P.M.; Alvarez-Ponce, D. Phylogenetic Distribution of CMP-Neu5Ac Hydroxylase (CMAH), the Enzyme Synthetizing the Proinflammatory Human Xenoantigen Neu5Gc. Genome Biol. Evol. 2018, 10(1), 207–219. DOI: 10.1093/gbe/evx251

Nemanichvili, N.; Spruit, C.M.; Berends, A.J.; Gröne, A.; Rijks, J.M.; Verheije, M.H.; De Vries, R.P. Wild and Domestic Animals Variably Display Neu5Ac and Neu5Gc Sialic Acids. Glycobiology 2022, 32(9), 791–802. DOI: 10.1093/glycob/cwac033

Alisson-Silva, F.; Kawanishi, K.; Varki, A. Human

Risk of Diseases Associated with Red Meat Intake: Analysis of Current Theories and Proposed Role for Metabolic Incorporation of a Non-Human Sialic Acid. Mol. Aspects Med. 2016, 51, 16–30. DOI: 10.1016/j.mam.2016.07.002

Yao, H. L.; Conway, L. P.; Wang, M. M.; Huang, K.; Liu, L.; Voglmeir, J. Quantification of Sialic Acids in Red Meat by UPLC-FLD Using Indoxylsialosides as Internal Standards. Glycoconj. J. 2016, 33(2), 219–226. DOI: 10.1007/s10719-016-9659-1

Perota, A.; Galli, C. N-Glycolylneuraminic Acid (Neu5Gc) Null Large Animals by Targeting the CMP-Neu5Gc Hydroxylase (CMAH). Front. Immunol. 2019, 10, Art. No: 2396. DOI: 10.3389/fimmu.2019.02396

Diaz, S. L.; Padler-Karavani, V.; Ghaderi, D.; Hurtado-Ziola, N.; Yu, H.; Chen, X.; Brinkman-Van Der Linden, E. C. M.; Varki, A.; Varki, N. M. Sensitive and Specific Detection of the Non-Human Sialic Acid N-Glycolylneuraminic Acid In Human Tissues and Biotherapeutic Products. PLoS ONE 2009, 4(1), Art. No: e4241. DOI: 10.1371/journal.pone.0004241

Shewell, L.K.; Wang, J.J.; Paton, J.C.; Paton, A.W.; Day, C.J.; Jennings, M.P. Detection of N-Glycolylneuraminic Acid Biomarkers in Sera from Patients with Ovarian Cancer Using an Engineered N-Glycolylneuraminic Acid-Specific Lectin SubB2M. Biochem. Biophys. Res. Commun. 2018, 507(1–4), 173–177. DOI: 10.1016/j.bbrc.2018.11.001

Hedlund, M.; Padler-Karavani, V.; Varki, N.M.; Varki, A. Evidence for a Human-Specific Mechanism for Diet and Antibody-Mediated Inflammation in Carcinoma Progression. Proc. Natl. Acad. Sci. 2008, 105(48), 18936–18941. DOI: 10.1073/pnas.0803943105

Samraj, A.N.; Läubli, H.; Varki, N.; Varki, A. Involvement of a Non-Human Sialic Acid in

Human Cancer. Front. Oncol. 2014, 4, Art. No: 33. DOI: 10.3389/fonc.2014.00033

Blanco, R.; Domínguez, E.; Morales, O.; Blanco, D.; Martínez, D.; Rengifo, C.E.; Viada, C.; Cedeño, M.; Rengifo, E.; Carr, A. Prognostic Significance of N-Glycolyl GM3 Ganglioside Expression in Non-Small Cell Lung Carcinoma Patients: New Evidences. Pathol. Res. Int. 2015, 2015, 1–12. DOI: 10.1155/2015/132326

Hayashi, N.; Chiba, H.; Kuronuma, K.; Go, S.; Hasegawa, Y.; Takahashi, M.; Gasa, S.; Watanabe, A.; Hasegawa, T.; Kuroki, Y.; Inokuchi, J.; Takahashi, H. Detection of N ‐glycolyated Gangliosides in Non‐

small‐cell Lung Cancer Using GMR 8 Monoclonal Antibody. Cancer Sci. 2013, 104(1), 43–47. DOI: 10.1111/cas.12027

Wang, J.; Shewell, L.K.; Day, C.J.; Jennings, M.P.

N-Glycolylneuraminic Acid as a Carbohydrate Cancer Biomarker. Transl. Oncol. 2023, 31, Art. No: 101643. DOI: 10.1016/j.tranon.2023.101643

Tangvoranuntakul, P.; Gagneux, P.; Diaz, S.; Bardor, M.; Varki, N.; Varki, A.; Muchmore, E. Human Uptake and Incorporation of an Immunogenic Nonhuman Dietary Sialic Acid. Proc. Natl. Acad. Sci. 2003, 100(21), 12045–12050. DOI: 10.1073/pnas.2131556100

Bousquet, P.A.; Sandvik, J.A.; Jeppesen Edin, N.F.; Krengel, U. Hypothesis: Hypoxia Induces de Novo Synthesis of NeuGc Gangliosides in Humans through CMAH Domain Substitute. Biochem. Biophys. Res. Commun. 2018, 495(1), 1562–1566. DOI: 10.1016/j.bbrc.2017.11.183

Guerrero-Flores, G.N.; Pacheco, F.J.; Boskovic, D.S.; Pacheco, S.O.S.; Zhang, G.; Fraser, G.E.; Miles, F.L. Sialic Acids Neu5Ac and KDN in Adipose Tissue Samples from Individuals Following Habitual Vegetarian or Non-Vegetarian Dietary Patterns. Sci. Rep. 2023, 13(1), Art. No: 12593. DOI: 10.1038/s41598-023-38102-z

Jakub Iwaszczuk

kuba.iwaszczuk@gmail.com

Affiliation:

University of Białystok, Faculty of Chemistry Poland

Aneta Baj

aneta.baj@uwb.edu.pl

Affiliation:

University of Białystok, Faculty of Chemistry Poland

Piotr Wałejko

pwalejko@uwb.edu.pl

Affiliation:

University of Białystok, Faculty of Chemistry Poland

Sialic acids – structure and properties

Jakub Iwaszczuk

Aneta Baj

Piotr Wałejko

Abstract

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