58902-60-6 , Disialyloctasaccharide ,
a2,6-Sialylglycan; a2,6-SG
C76H125N5O57 / 2020.81
MFCD29905032
Disialyloctasaccharide is a sialylated glycan that is found in human serum. It is a diagnostic marker for cancer, and has been shown to be elevated in women with breast cancer. Disialyloctasaccharide can also be used as a biomarker for depression. The amino acid sequence of this glycan has been determined, and it has been shown that the protein glycosylation of disialyloctasaccharide is quantified by measuring the relative amount of sialic acid residues in the molecule. Disialyloctasaccharide can be used as a biomarker for eukaryotes, including yeast and mammals. This glycan also has anti-tumor activity, which may be due to its ability to bind to receptors on tumor cells.
Disialyloctasaccharide: Definition and Background
Disialyloctasaccharide (DSO) is a complex carbohydrate molecule composed of eight sugar units and two sialic acid molecules. It belongs to the family of glycoconjugates, which are complex macromolecules composed of carbohydrates covalently attached to proteins, lipids or other carbohydrates. DSO is a naturally occurring compound found in human milk and is known for its immunomodulatory and anti-inflammatory properties. The molecule's structure is thought to resemble that of cell surface receptors, which enables it to interact with immune cells and modulate their functions.
Physical and Chemical Properties
DSO is a white, amorphous solid that is soluble in water and exhibits a high molecular weight of approximately 2,600 daltons. The molecule's structure is characterized by the presence of two sialic acid molecules, which play an essential role in its biological activity. Sialic acid is a type of sugar molecule that is commonly found on cell surfaces and is involved in many physiological functions, including cell signaling and recognition.
Synthesis and Characterization
DSO can be synthesized in the laboratory using a variety of methods, including chemical synthesis, chemoenzymatic synthesis, and enzymatic synthesis. The most common method of synthesis is chemical synthesis, which involves the use of chemical reagents to assemble the molecule's sugar units and sialic acid molecules. The resulting product is then purified by various chromatographic methods, including ion exchange chromatography and gel filtration chromatography.
Analytical Methods
The characterization of DSO is typically done using high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy. HPLC is commonly used to analyze the purity and homogeneity of the synthesized DSO, whereas MS and NMR are used to identify the molecular weight and chemical structure of the molecule.
Biological Properties
DSO has been shown to exhibit numerous biological properties, including immunomodulatory and anti-inflammatory effects. In particular, DSO has been found to modulate the activity and function of various immune cells, such as T cells, B cells, and natural killer cells, by interacting with their surface receptors. Additionally, DSO has been shown to reduce the production of pro-inflammatory cytokines, thus limiting the inflammatory response.
Toxicity and Safety in Scientific Experiments
The toxicity and safety of DSO have been extensively studied in various animal models, and the compound has been found to be safe at therapeutic doses. However, higher doses of DSO can cause some adverse effects, such as gastrointestinal disturbances, headaches, and mild allergic reactions. Therefore, the use of DSO in human trials must be carefully regulated and monitored.
Applications in Scientific Experiments
DSO has been extensively studied in various scientific experiments due to its immunomodulatory and anti-inflammatory properties. It has been shown to be effective in the treatment of various autoimmune diseases, such as rheumatoid arthritis, multiple sclerosis, and lupus. Additionally, DSO has been shown to have potential therapeutic applications in cancer treatment, as it can modulate the activity of immune cells, thus enhancing the body's ability to fight cancer.
Current State of Research
Research on DSO is ongoing, with many studies focusing on its immunomodulatory and anti-inflammatory properties. Additionally, there are several ongoing clinical trials investigating the therapeutic potential of DSO in various autoimmune diseases and cancer.
Potential Implications in Various Fields of Research and Industry
DSO has potential implications in various fields of research and industry, such as drug development and biomedical research. Its immunomodulatory and anti-inflammatory properties make it an attractive candidate for the development of novel therapeutics for autoimmune diseases and cancer. Additionally, DSO has potential applications in the development of immunomodulatory agents, vaccines, and other biologics.
Limitations and Future Directions
Despite its promising therapeutic potential, there are several limitations to the use of DSO in clinical settings. For instance, the synthesis of DSO can be challenging and costly, which limits its availability and accessibility. Additionally, there is still much to be learned about the mechanisms by which DSO interacts with the immune system and modulates its functions.
Future directions for research on DSO include the development of more efficient and cost-effective methods of synthesis, the identification of novel therapeutic targets, and the elucidation of the molecular mechanisms underlying its immunomodulatory and anti-inflammatory effects. Furthermore, the potential of DSO as a modulator of the gut microbiome and its role in the gut-brain-axis needs further exploration.
CAS Number | 58902-60-6 |
Product Name | Disialyloctasaccharide |
IUPAC Name | (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[[(2R,3R,4S,5S,6S)-4-[(2R,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4S,5R,6R)-6-[[(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R,3S,4R,5R)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy-3,5-dihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
Molecular Formula | C76H125N5O57 |
Molecular Weight | 2020.8 g/mol |
InChI | InChI=1S/C76H125N5O57/c1-19(90)77-24(8-82)41(100)58(29(99)11-85)131-70-57(116)63(134-72-65(54(113)45(104)31(13-87)125-72)136-67-40(81-23(5)94)50(109)60(33(15-89)127-67)133-69-56(115)52(111)47(106)36(130-69)18-123-76(74(119)120)7-26(96)38(79-21(3)92)62(138-76)43(102)28(98)10-84)48(107)34(128-70)16-121-71-64(53(112)44(103)30(12-86)124-71)135-66-39(80-22(4)93)49(108)59(32(14-88)126-66)132-68-55(114)51(110)46(105)35(129-68)17-122-75(73(117)118)6-25(95)37(78-20(2)91)61(137-75)42(101)27(97)9-83/h8,24-72,83-89,95-116H,6-7,9-18H2,1-5H3,(H,77,90)(H,78,91)(H,79,92)(H,80,93)(H,81,94)(H,117,118)(H,119,120)/t24-,25-,26-,27+,28+,29+,30+,31+,32+,33+,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+,44+,45+,46-,47-,48+,49+,50+,51-,52-,53-,54-,55+,56+,57-,58+,59+,60+,61+,62+,63-,64-,65-,66-,67-,68-,69-,70-,71-,72+,75+,76+/m0/s1 |
InChI Key | YQWQHDSJVQCIQT-BNIJKCBMSA-N |
SMILES | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OCC2C(C(C(C(O2)OC3C(OC(C(C3O)NC(=O)C)OC4C(C(C(OC4OCC5C(C(C(C(O5)OC(C(CO)O)C(C(C=O)NC(=O)C)O)O)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)COC9(CC(C(C(O9)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)O)NC(=O)C)O)CO)O)O)CO)O)O)O)O |
Canonical SMILES | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OCC2C(C(C(C(O2)OC3C(OC(C(C3O)NC(=O)C)OC4C(C(C(OC4OCC5C(C(C(C(O5)OC(C(CO)O)C(C(C=O)NC(=O)C)O)O)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)COC9(CC(C(C(O9)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)O)NC(=O)C)O)CO)O)O)CO)O)O)O)O |
Isomeric SMILES | CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)NC(=O)C)O[C@H]4[C@H]([C@@H]([C@H](O[C@@H]4OC[C@@H]5[C@H]([C@@H]([C@@H]([C@@H](O5)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)NC(=O)C)O)O)O[C@@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO[C@@]9(C[C@@H]([C@H]([C@@H](O9)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)O)NC(=O)C)O)CO)O)O)CO)O)O)O)O |
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