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CAS 3063-71-6

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CMP-Neu5Ac

Description:
CMP-Neu5Ac, or Cytidine 5'-monophosphate N-acetylneuraminic acid, is a nucleotide sugar that plays a crucial role in the biosynthesis of sialic acids, which are important components of glycoproteins and glycolipids. This compound is characterized by its structure, which includes a cytidine moiety linked to a sialic acid derivative, specifically N-acetylneuraminic acid. CMP-Neu5Ac is typically found in cellular processes involving glycosylation, influencing cell-cell interactions, signaling, and immune responses. It is soluble in water and exhibits stability under physiological conditions, making it suitable for various biochemical applications. CMP-Neu5Ac serves as a donor substrate for sialyltransferases, enzymes that catalyze the transfer of sialic acid to growing carbohydrate chains. Its role in cellular recognition and adhesion highlights its significance in both health and disease, particularly in viral infections and cancer biology. Overall, CMP-Neu5Ac is a vital molecule in glycobiology, contributing to the complexity of cellular interactions and functions.
Formula:C20H31N4O16P
InChI:InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1
InChI key:InChIKey=TXCIAUNLDRJGJZ-BILDWYJOSA-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(C)=O)[C@@H](O)C3)[H]
Synonyms:
  • (2R,4S,5R,6R)-5-(acetylamino)-2-{[{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)
  • (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid
  • 5-(acetylamino)-2-{[{[5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)
  • 5′-Cytidylic acid, 5′→2-ester with 5-acetamido-3,5-dideoxy-<span class="text-smallcaps">D</smallcap>-glycero-<smallcap>D</span>-galacto-nonulopyranosonic acid
  • <span class="text-smallcaps">D</smallcap>-glycero-<smallcap>D</span>-galacto-Nonulopyranosonic acid, 5-acetamido-3,5-dideoxy-, 2→5′-monoester with cytidylic acid
  • <span class="text-smallcaps">D</smallcap>-glycero-β-<smallcap>D</span>-galacto-2-Nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-, 2-(hydrogen 5′-cytidylate)
  • CMP-N-acetylneuraminic acid
  • CMP-Neu5Ac
  • CMP-NeuAc
  • CMP-b-D-Sialic Acid, DisodiumSalt
  • See more synonyms
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