What is Sialylated Glycan?
Sialic acid is present at the terminal ends of glycan chains in glycoproteins, glycolipids, and milk oligosaccharides. In the human body, sialic acid exists as N-acetylneuraminic acid. Its distribution spans throughout the body, including cell membranes such as those of red blood cells, blood vessels, airways, nerves, as well as secretions like breast milk and saliva. Sialic acid is believed to play an important role in brain formation and development, especially considering its abundance in gangliosides and glycolipids found in the brain, as well as its large presence in colostrum during infancy, which is considered crucial for brain formation.
Sialylated glycans have been shown to play critical roles in various biological processes, including cell-cell recognition, cell differentiation, bacterial and viral infections, and cellular signaling. For instance, the initiation of influenza infection is well-known to begin with the binding of hemagglutinin on the virus surface to sialic acid on the cell surface.1) Recent studies on Siglec (Sialic acid-binding Immunoglobulin-type Lectin) have highlighted its association with autoimmune diseases, cancer, and its role as an immune checkpoint regulator.2,3)
Adequate quantities of sialylated glycans are essential for advancing research in glycan-related studies. However, sialylated glycans with complex structures are naturally present only in trace amounts, making them difficult to obtain sufficient quantities.
Sialylated Glycans-related Products
We offer a variety of glycans with various aglycones, including ceramide commonly found in gangliosides. We provide glycans modified with pNP groups, widely used in enzyme activity assays, as well as those conjugated with aminoalkyl groups suitable for glycan-protein conjugation. Additionally, we offer glycans modified with azidoalkyl groups, which are compatible with click chemistry, allowing you to choose the appropriate option based on your specific needs. Our products cover sialic acid residues not only in the typical N-Ac form but also in the N-Gc form, which is not usually present in humans. Moreover, we provide a wide range of building block products, monosaccharides and disaccharides, that are highly utilized in sialic acid-containing glycan chemical synthesis. If you require sialylated glycans not listed in our product catalog, please feel free to contact us, as we are happy to assist you.
Glycolipid Oligosaccharides / Reducing End Free Glycans
We offer products that correspond to ceramides commonly found in gangliosides, glycans with varying ceramide lengths, and glycans with free reducing ends.
pNP Glycosides
We introduce pNP (p-nitrophenyl) groups at the reducing ends, widely used for enzyme activity assays.
Aminoalkyl Glycosides / Azidoalkyl Glycosides
Glycans suitable for various applications, including glycan-protein conjugation, are available. Azidoalkyl glycosides are compatible with click chemistry.
Glycolipid Oligosaccharides
G0489 Ganglioside GM3
G0419 Ganglioside GM3[d18:1, (Carbon-13)C16:0] G0422 Ganglioside GM3 (phyto-type) G0510 Ganglioside GM3(Neu5Gc) (phyto-type) G0421 Ganglioside GM1[d18:1, (Carbon-13)C16:0] S0910 Sialyl Neolactotetraosylceramide (= Sialyl nLc4Cer) G0593 SialylGb5 Ceramide (= SSEA-4)
Glyco Amino Acids / Glyco Peptides
Reducing End Free Glycans
S0885 3'-Sialyllactose Sodium Salt
S0886 6'-Sialyllactose Sodium Salt S0849 Sialyl Lewis X-Lactose
D4065 Disialyloctasaccharide N1064 Neu5Gcα(2-6) N-Glycan
N1065 Neu5Acα(2-6) N-Glycan N1182 Neu5Gcα(2-6) core 6-Fucosylated N-Glycan
MP Glycosides / pNP Glycosides
N0792 Neu5Acα(2-6)GalβMP Glycoside
N0793 Neu5Acα(2-3)GalβMP Glycoside N0794 Neu5Gcα(2-6)GalβMP Glycoside
N0890 Neu5Acα(2-6)GalNAc-α-pNP N0853 Neu5Acα(2-3)Galβ(1-3)GlcNAc-β-pNP
N0854 Neu5Acα(2-3)Galβ(1-4)GlcNAc-β-pNP N0855 Neu5Acα(2-6)Galβ(1-3)GlcNAc-β-pNP
N0856 Neu5Acα(2-6)Galβ(1-4)GlcNAc-β-pNP
N0860 Neu5Acα(2-3)Galβ(1-4)Glc-β-pNP G0353 Galβ(1-4)[Neu5Acα(2-6)]GlcNAc-β-pNP
G0345 Galβ(1-3)[Neu5Acα(2-6)]GalNAc-β-pNP G0377 Galβ(1-3)[Neu5Acα(2-6)]GalNAc-α-pNP
G0378 GlcNAcβ(1-3)[Neu5Acα(2-6)]GalNAc-α-pNP
N0913 Disialylnonasaccharide-β-pNP Aminoalkyl Glycosides / Azidoalkyl Glycosides
N1147 Neu5Acα(2-6)Gal-β-propylamine
N0950 Neu5Acα(2-6)Galβ(1-4)GlcNAc-β-ethylamine N1249 Neu5Acα(2-3)Gal-β-propylazideN1146Neu5Acα(2-3)Gal-β-propylamine
N1267 Neu5Acα(2-3)Galβ(1-4)GlcNAc-β-propylamine N1258 Neu5Acα(2-3)Galβ(1-4)Glc-β-propylamine
N1259 Neu5Gcα(2-3)Galβ(1-4)Glc-β-propylamine G0440 Galβ(1-3)[Neu5Acα(2-6)]GalNAc-α-propylamine
N1117 Neu5Acα(2-6)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-4)GlcNAc-β-propylamine
N1118 Neu5Acα(2-6)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-4)GlcNAc-β-propylamine S0922 Sialyl Lewis X-Lactose Ethylazide
S0923 Sialyl Lewis X-Lactose Ethylamine
D4217 Disialylnonasaccharide-β-ethylazide
Sialylated Building Blocks
M2329 Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-β-D-galacto-2-nonulopyranosylonate
M1706 Neu5Ac[1Me,4789Ac]-SPh M2695 Neu5Ac[1Me,478Ac,9N3]-β-SPhM2696Neu5GcAc[1Me,478Ac,9N3]-β-SPh
M1707 2,4,7,8,9-Penta-O-acetyl-N-acetylneuraminic Acid Methyl Ester M2319 Methyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-β-D-galacto-2-nonulopyranosylonate
A1822 4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester M1729 Neu5Troc[1Me,4789Ac]α(2-3)Gal[26Bn]-β-MP
M1763 Neu5GcAc[1Me,4789Ac]α(2-6)Gal[24Bz,3Bn]-β-MP
M1761 Neu5Ac[1Me,4789Ac]α(2-6)Gal[24Bz,3Bn]-β-MPN0846Neu5Ac[1Me,4789Ac]α(2-3)Gal[246Bz]-β-MP N0816 Neu5GcAc[1Me,4789Ac]α(2-3)Gal[246Bz]-β-MP
Partially Modified Sialic Acid Analogs
A2492 N-Acetyl-9-deoxy-9-fluoroneuraminic Acid
A2511 N-Acetyl-9-deoxy-9-aminoneuraminic Acid
A3414 N-Acetyl-9-O-acetylneuraminic Acid
A3415 N-Acetyl-9-deoxy-9-acetamidoneuraminic Acid
A3416 N-Acetyl-2-deoxy-2-azido-α-neuraminic Acid
A3458 N-Acetyl-9-azido-9-deoxyneuraminic Acid A3483 5-Azidoneuraminic Acid
Detection Tools for Sialylated Glycans
Sialylated glycans play diverse roles within the body. Selectins, cell surface molecules involved in leukocyte-endothelial cell adhesion, strongly bind to glycans with sialyl Lex and sialyl Lea structures. Particularly, the molecular interaction between L-selectin and ligand glycans is implicated not only in lymphocyte homing but also in the recruitment of leukocytes to inflammatory sites in chronic inflammation. Therefore, glycans serving as ligands for selectins are expected to be anti-inflammatory agents, and numerous development studies have been conducted.4) Additionally, the sialyl Lea antigen is highly expressed in pancreatic cancer, biliary tract cancer, and colorectal cancer, and the CA19-9 antibody against this antigen is used for cancer diagnosis. Other tumor markers like SLX (sialyl Lex) and STN (sialyl Tn), which possess sialic acid, are also utilized for cancer diagnosis, vaccines, and immunotherapy.5) We offer antibodies against sialylated glycans, including blood group antigens.
Anti-Glycan Antibodies
A2505 Anti-GM1 Monoclonal Antibody
A2576 Anti-GM2 Monoclonal Antibody A2582 Anti-GM3 Monoclonal Antibody
A2507 Anti-GD1a Monoclonal Antibody A2508 Anti-GD1b Monoclonal Antibody
A3338 Anti-GD2 Monoclonal Antibody A2580 Anti-GD3 Monoclonal Antibody
A2702 Anti-GT1a Monoclonal Antibody A2732 Anti-GT1b Monoclonal Antibody
A2662 Anti-GQ1b Monoclonal Antibody A2701 Anti-GalNAc-GD1a Monoclonal Antibody (2A3D2) A2509 Anti-Sialyl Lewis A Monoclonal Antibody (2D3)
A2584 Anti-Sialyl Lewis A Monoclonal Antibody (1H4) A2849 Anti-Sialyl Lewis X Monoclonal Antibody
Lectins
R0230 rPSL1a-Biotin [for Siaα(2-6)Gal]
R0235 rPSL1a-LecBeads [for Siaα(2-6)Gal] R0225 Recombinant Polyporus squamosus lectin (= rPSL1a) expressed in Escherichia coli
D3690 DNS-SGN
N1075 Neu5Gcα(2-6) N-Glycan 2AB (500pmol/vial) N1073 Neu5Acα(2-6) N-Glycan 2AB (500pmol/vial)
N1183 Neu5Gcα(2-6) core 6-Fucosylated N-Glycan 2AB (500pmol/vial) M3031 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic Acid Sodium Salt
References
- 1) Neuraminidase inhibitors for influenza
- 2) Small RNAs are modified with N-glycans and displayed on the surface of living cells
- R. A. Flynn, K. Pedram, S. A. Malaker, P. J. Batista, B. A.H. Smith, A. G. Johnson, B. M. George, K. Majzoub, P. W. Villalta, J. E. Carette, C. R. Bertozzi, Cell 2021, 184, 3109.
- 3) Siglecs-7/9 function as inhibitory immune checkpoints in vivo and can be targeted to enhance therapeutic antitumor immunity
- 4) Sulfated L-selectin ligands as a therapeutic target in chronic inflammation
- 5) Tumour-associated carbohydrate antigens in breast cancer