Sialic acids – structure and properties
DOI:
https://doi.org/10.56782/pps.244Keywords:
sialic acids, Neu5Ac, Neu5Gc, cancer biomarkersAbstract
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.
Downloads
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. DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/10.1016/bs.mie.2017.06.003
Varki, A. Biological Roles of Glycans. Glycobiology 2017, 27(1), 3–49. DOI: 10.1093/glycob/cww086 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/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 DOI: https://doi.org/10.1038/s41598-023-38102-z
Downloads
Published
Issue
Section
License
Copyright (c) 2024 Jakub Iwaszczuk, Aneta Baj, Piotr Wałejko

This work is licensed under a Creative Commons Attribution 4.0 International License.
For all articles published in Prospects in Pharmaceutical Sciences copyright is retained by the authors. The journal publishes articles in the Open Access policy, within the CC BY 4.0 licence.
This is a human-readable summary of (and not a substitute for) the license. Disclaimer.
You are free to:
Share — copy and redistribute the material in any medium or format
Adapt — remix, transform, and build upon the material for any purpose, even commercially.
The licensor cannot revoke these freedoms as long as you follow the license terms.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
No additional restrictions — You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
Notices:
You do not have to comply with the license for elements of the material in the public domain or where your use is permitted by an applicable exception or limitation.
No warranties are given. The license may not give you all of the permissions necessary for your intended use. For example, other rights such as publicity, privacy, or moral rights may limit how you use the material.