98300-80-2

Basic information

• Product Name: cytidine monophosphate-N-glycoloylneuraminic acid
• Synonyms: cytidine monophosphate-N-glycoloylneuraminic acid;Cytidine-5'-monophospho-N-glycolylneuraminic acid disodium salt, 98%
• CAS NO: 98300-80-2
• Molecular Formula: C₂₀H₃₁N₄O₁₇P
• Molecular Weight: 630.450501
• Mol File: 98300-80-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.09g/cm³
• Refractive Index: 1.751
• CAS DataBase Reference: cytidine monophosphate-N-glycoloylneuraminic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cytidine monophosphate-N-glycoloylneuraminic acid(98300-80-2)
• EPA Substance Registry System: cytidine monophosphate-N-glycoloylneuraminic acid(98300-80-2)

Safety Data

• Hazardous Substances Data: 98300-80-2(Hazardous Substances Data)

Usage

General Description

Cytidine monophosphate-N-glycoloylneuraminic acid (CMP-Neu5Gc) is a derivative of cytidine monophosphate and an important precursor in the synthesis of the sialic acid Neu5Gc. Sialic acids are a family of nine-carbon sugars found in abundance on the surface of animal cells and play essential roles in cell-cell recognition and adhesion. CMP-Neu5Gc is involved in various biological processes, including immune responses and the modulation of cell signaling. However, it has also been implicated in certain diseases and health issues, particularly in relation to its incorporation into human tissues through dietary sources such as red meat and dairy products. The presence of CMP-Neu5Gc in human cells has been linked to chronic inflammation, certain types of cancer, and autoimmune diseases, making it an area of interest in both biomedical research and nutrition.

InChI:InChI=1/C20H31N4O17P/c21-10-1-2-24(19(35)22-10)17-15(32)14(31)9(39-17)6-38-42(36,37)41-20(18(33)34)3-7(27)12(23-11(29)5-26)16(40-20)13(30)8(28)4-25/h1-2,7-9,12-17,25-28,30-32H,3-6H2,(H,23,29)(H,33,34)(H,36,37)(H2,21,22,35)/t7-,8+,9+,12+,13+,14+,15+,16+,17?,20+/m0/s1

Upstream product

• 4710-95-6 D-mannosamine hydrochloride 
• 40632-06-2 2',3'-O,N⁴-triacetylcytidine 
• 65-46-3 CYTIDINE 
• 194665-70-8 C₄₀H₅₃N₄O₂₅P 
• 194665-66-2 allyl 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 5-[2-(acetoxy) acetamido]-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphite 
• 175877-09-5 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 5-[2-(acetoxy)acetamido]-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate 
• 194665-58-2 2',3'-O,N⁴-triacetyl-5'-tert-butyldiphenylsilyl cytidine 
• 175877-08-4 methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate 
• 188786-02-9 2-allyl-2'-(2',3',N⁴-triacetyl-cytidin-5')-yl-N,N'-diisopropylphosphoramidite 
• 58479-65-5 5'-O-(tert-butyldiphenylsilyl)cytidine 
• 118865-39-7 methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl chlorid)onate 
• 113-24-6 sodium pyruvate 
• 65-47-4 cytidine triphosphate 
• 80124-69-2 5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid 

Relevant articles and documents

Efficient chemoenzymatic synthesis of O-linked sialyl oligosaccharides

The tumor associated Tn (GalNAcα(1-1)-Thr/Ser)- and T (Galβ(1-3)-GalNAcα(1-1)Thr/Ser)-antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcα2,6-sialyltransferase (chST6GalNAc I) and a porcine Galβ(1-3)GalNAcα-2,3-sialyltransferase (pST3Gal I). Using these enzymes, the common O-linked sialosides Neu5Acα(2-6)GalNAcα(1-1)Thr, Galβ(1-3)[Neu5Acα(2-6)] GalNAcα(1-1)Thr, Neu5Acα(2-3)Galβ(1-3)GalNAcα(1-1)Thr, and Neu5Acα(2-3)Galβ(1-3)[Neu5Acα(2-6)]GalNAcα(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

Synthesis of CMP-sialic acid conjugates: Substrates for the enzymatic synthesis of natural and designed sialyl oligosaccharides

The syntheses of several congeners of CMP-NeuAc are described. These compounds are substrates for enzymatic glycosylation.