CAS 98300-80-2

CMP-NeuGc

Description:

CMP-NeuGc, or Cytidine Monophosphate N-Glycolylneuraminic Acid, is a nucleotide sugar derivative that plays a significant role in cellular processes, particularly in the biosynthesis of glycoproteins and glycolipids. It is characterized by the presence of a glycolyl group attached to the neuraminic acid moiety, which distinguishes it from its counterpart, CMP-NeuAc (Cytidine Monophosphate N-Acetylneuraminic Acid). CMP-NeuGc is involved in various biological functions, including cell signaling and immune responses, and is known to be incorporated into glycoconjugates in certain mammalian cells. Its structure allows it to participate in sialylation processes, which are crucial for the proper functioning of glycoproteins. CMP-NeuGc is of particular interest in research related to cancer biology and immunology, as it can influence cell interactions and immune evasion mechanisms. However, it is important to note that humans do not naturally synthesize NeuGc due to a genetic mutation, making its study relevant for understanding evolutionary biology and potential therapeutic applications.

Formula: C₂₀H₃₁N₄O₁₇P

InChI: InChI=1S/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

InChI key: InChIKey=HOEWKBQADMRCLO-UIUGZIMDSA-N

SMILES: O(P(OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C(=O)N=C(N)C=C2)(=O)O)[C@]3(C(O)=O)O[C@@]([C@@H]([C@@H](CO)O)O)([C@H](NC(CO)=O)[C@@H](O)C3)[H]

Synonyms:

• D-glycero-β-D-galacto-2-Nonulopyranosonic acid, 3,5-dideoxy-5-[(hydroxyacetyl)amino]-, 2-(hydrogen 5′-cytidylate)
• CMP-Neu5Gc.2Na
• β-Neuraminic acid, N-(hydroxyacetyl)-, 2-(hydrogen 5′-cytidylate)
• β-Neuraminic acid, N-(2-hydroxyacetyl)-, 2-(hydrogen 5′-cytidylate)
• CMP-NeuGc

CMP-Neu5Gc sodium salt

CAS: 98300-80-2

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Formula: C₂₀H₂₉N₄Na₂O₁₇P

Molecular weight: 674.41 g/mol

Ref: 3D-MC00696