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3063-71-6,MFCD00870237
Catalog No.:AA00BE4N

3063-71-6 | CYTIDINE 5'-MONOPHOSPHO-N-

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Purity
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1mg
≥85%
in stock  
$159.00   $112.00
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5mg
≥85%
in stock  
$438.00   $307.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE4N
Chemical Name:
CYTIDINE 5'-MONOPHOSPHO-N-
CAS Number:
3063-71-6
Molecular Formula:
C20H31N4O16P
Molecular Weight:
614.4511
MDL Number:
MFCD00870237
SMILES:
OC[C@H]([C@H]([C@@H]1O[C@](C[C@@H]([C@H]1NC(=O)C)O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(nc1=O)N)O)C(=O)O)O)O
Properties
Properties
 
Form:
Solid  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
1120  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
16  
Hydrogen Bond Donor Count:
10  
Rotatable Bond Count:
11  
XLogP3:
-6.7  

Downstream Synthesis Route

[1]LiebigsAnnalenderChemie,1990,p.1101-1105

[2]JournaloftheAmericanChemicalSociety,1992,vol.114,p.3901-3910

3063-71-6    5965-66-2   
2,6-sialyllactose 

[1]Simon,EthanS.;Bednarski,MarkD.;Whitesides,GeorgeM.[JournaloftheAmericanChemicalSociety,1988,vol.110,#21,p.7159-7163]

3063-71-6    6813-81-6    489-46-3    63-37-6   
(2S,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylicacid 
 
(2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylicacid 

[1]JournaloftheAmericanChemicalSociety,1998,vol.120,p.1357-1362

[1]Bioscience,BiotechnologyandBiochemistry,2005,vol.69,p.1944-1950

[1]Bioscience,BiotechnologyandBiochemistry,2005,vol.69,p.1944-1950

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Title: The CMP-sialic acid transporter is localized in the medial-trans Golgi and possesses two specific endoplasmic reticulum export motifs in its carboxyl-terminal cytoplasmic tail.

Journal: The Journal of biological chemistry 20061013

Title: Humanization of yeast to produce complex terminally sialylated glycoproteins.

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Title: Isolation and analysis of a baculovirus vector that supports recombinant glycoprotein sialylation by SfSWT-1 cells cultured in serum-free medium.

Journal: Biotechnology and bioengineering 20060905

Title: Expression of a functional Drosophila melanogaster CMP-sialic acid synthetase. Differential localization of the Drosophila and human enzymes.

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Title: Enhancing recombinant glycoprotein sialylation through CMP-sialic acid transporter over expression in Chinese hamster ovary cells.

Journal: Biotechnology and bioengineering 20060405

Title: Effects of elevated ammonium on glycosylation gene expression in CHO cells.

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Title: Cytidine 5'-monophosphate (CMP)-induced structural changes in a multifunctional sialyltransferase from Pasteurella multocida.

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Title: Crystallization and preliminary X-ray crystallographic analysis of the alpha-2,6-sialyltransferase PM0188 from Pasteurella multosida.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20060201

Title: Expression of human CMP-N-acetylneuraminic acid synthetase and CMP-sialic acid transporter in tobacco suspension-cultured cell.

Journal: Biochemical and biophysical research communications 20060127

Title: Functional expression of the CMP-sialic acid transporter in Escherichia coli and its identification as a simple mobile carrier.

Journal: Glycobiology 20060101

Title: Characterization of a mutation and an alternative splicing of UDP-galactose transporter in MDCK-RCAr cell line.

Journal: Biochimica et biophysica acta 20060101

Title: Bacteria and cancer: cause, coincidence or cure? A review.

Journal: Journal of translational medicine 20060101

Title: Metabolic engineering of microbes for oligosaccharide and polysaccharide synthesis.

Journal: Microbial cell factories 20060101

Title: One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities.

Journal: Nature protocols 20060101

Title: Enzymatic synthesis of cytidine 5'-monophospho-N-acetylneuraminic acid.

Journal: Bioscience, biotechnology, and biochemistry 20051001

Title: The intracellular concentration of sialic acid regulates the polysialylation of the neural cell adhesion molecule.

Journal: FEBS letters 20050912

Title: Gene-expression profiles for five key glycosylation genes for galactose-fed CHO cells expressing recombinant IL-4/13 cytokine trap.

Journal: Biotechnology and bioengineering 20050605

Title: Engineering intracellular CMP-sialic acid metabolism into insect cells and methods to enhance its generation.

Journal: Biochemistry 20050524

Title: Genetic complementation reveals a novel human congenital disorder of glycosylation of type II, due to inactivation of the Golgi CMP-sialic acid transporter.

Journal: Blood 20050401

Title: Co-expression of two mammalian glycosyltransferases in the yeast cell wall allows synthesis of sLex.

Journal: FEMS yeast research 20050201

Title: Investigating hookworm genomes by comparative analysis of two Ancylostoma species.

Journal: BMC genomics 20050101

Title: Large-scale approaches for glycobiology.

Journal: Genome biology 20050101

Title: Chemoenzymatic synthesis of CMP-sialic acid derivatives by a one-pot two-enzyme system: comparison of substrate flexibility of three microbial CMP-sialic acid synthetases.

Journal: Bioorganic & medicinal chemistry 20041215

Title: Inflammation-induced transcriptional regulation of Golgi transporters required for the synthesis of sulfo sLex glycan epitopes.

Journal: Glycobiology 20041201

Title: Epigenetic reprogramming of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) in HIV-1-infected CEM T cells.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20041201

Title: Structure and function of vertebrate CMP-sialic acid synthetases.

Journal: Glycobiology 20041001

Title: Production of cytidine 5'-monophospho-N-acetyl-beta-D-neuraminic acid (CMP-sialic acid) using enzymes or whole cells entrapped in calcium pectate-silica-gel beads.

Journal: Biotechnology and applied biochemistry 20040801

Title: CMP-sialic acid synthetase of the nucleus.

Journal: Biochimica et biophysica acta 20040706

Title: Lineage-specific gene duplication and loss in human and great ape evolution.

Journal: PLoS biology 20040701

Title: Structural analysis of the sialyltransferase CstII from Campylobacter jejuni in complex with a substrate analog.

Journal: Nature structural & molecular biology 20040201

Title: Regulation of sialic acid O-acetylation in human colon mucosa.

Journal: Biological chemistry 20040201

Title: Cell surface sialylation and ecto-sialyltransferase activity of human CD34 progenitors from peripheral blood and bone marrow.

Journal: Glycoconjugate journal 20040101

Title: The crystal structure of murine CMP-5-N-acetylneuraminic acid synthetase.

Journal: Journal of molecular biology 20031205

Title: Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases.

Journal: The Journal of organic chemistry 20030711

Title: Substrate recognition by nucleotide sugar transporters: further characterization of substrate recognition regions by analyses of UDP-galactose/CMP-sialic acid transporter chimeras and biochemical analysis of the substrate specificity of parental and chimeric transporters.

Journal: The Journal of biological chemistry 20030620

Title: Chemoenzymatic synthesis of the sialyl-alpha-(2-->3')-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end.

Journal: Carbohydrate research 20030616

Title: A transgenic insect cell line engineered to produce CMP-sialic acid and sialylated glycoproteins.

Journal: Glycobiology 20030601

Title: Evidence for a sialic acid salvaging pathway in lepidopteran insect cells.

Journal: Glycobiology 20030601

Title: Functional relationships of the sialyltransferases involved in expression of the polysialic acid capsules of Escherichia coli K1 and K92 and Neisseria meningitidis groups B or C.

Journal: The Journal of biological chemistry 20030425

Title: Production of cytidine 5'-monophosphate N-acetylneuraminic acid using recombinant Escherichia coli as a biocatalyst.

Journal: Biotechnology and bioengineering 20021205

Title: Expression and functional characterization of a nucleotide sugar transporter from Drosophila melanogaster: relevance to protein glycosylation in insect cell expression systems.

Journal: Protein expression and purification 20021201

Title: [Minimal functional domain of cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuAc) synthetase from Escherichia coli].

Journal: Sheng wu gong cheng xue bao = Chinese journal of biotechnology 20021101

Title: Transport of UDP-galactose in plants. Identification and functional characterization of AtUTr1, an Arabidopsis thaliana UDP-galactos/UDP-glucose transporter.

Journal: The Journal of biological chemistry 20020906

Title: High-level expression of recombinant Neisseria CMP-sialic acid synthetase in Escherichia coli.

Journal: Protein expression and purification 20020701

Title: Nuclear localization signal of murine CMP-Neu5Ac synthetase includes residues required for both nuclear targeting and enzymatic activity.

Journal: The Journal of biological chemistry 20020531

Title: Regulation of the mannan-binding lectin pathway of complement on Neisseria gonorrhoeae by C1-inhibitor and alpha 2-macroglobulin.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20020415

Title: GPR99, a new G protein-coupled receptor with homology to a new subgroup of nucleotide receptors.

Journal: BMC genomics 20020101

Title: The human L-threonine 3-dehydrogenase gene is an expressed pseudogene.

Journal: BMC genetics 20020101

Title: Inhibition of CMP-sialic acid transport into Golgi vesicles by nucleoside monophosphates.

Journal: Biochemistry 20011127

Title: Microbial glycosyltransferases for carbohydrate synthesis: alpha-2,3-sialyltransferase from Neisseria gonorrheae.

Journal: Journal of the American Chemical Society 20011107

Title: Metabolic control of recombinant monoclonal antibody N-glycosylation in GS-NS0 cells.

Journal: Biotechnology and bioengineering 20011020

Title: Mannose-binding lectin accelerates complement activation and increases serum killing of Neisseria meningitidis serogroup C.

Journal: The Journal of infectious diseases 20011001

Title: The structure of CMP:2-keto-3-deoxy-manno-octonic acid synthetase and of its complexes with substrates and substrate analogs.

Journal: Journal of molecular biology 20010907

Title: Efficient biochemical engineering of cellular sialic acids using an unphysiological sialic acid precursor in cells lacking UDP-N-acetylglucosamine 2-epimerase.

Journal: FEBS letters 20010810

Title: Location and mechanism of alpha 2,6-sialyltransferase dimer formation. Role of cysteine residues in enzyme dimerization, localization, activity, and processing.

Journal: The Journal of biological chemistry 20010803

Title: Elongation of alternating alpha 2,8/2,9 polysialic acid by the Escherichia coli K92 polysialyltransferase.

Journal: Glycobiology 20010801

Title: Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N-acetylneuraminic acid (Neu5Ac) as substrates.

Journal: Glycobiology 20010801

Title: Nucleotide sugar transporters: biological and functional aspects.

Journal: Biochimie 20010801

Title: Glycoengineering of therapeutic glycoproteins: in vitro galactosylation and sialylation of glycoproteins with terminal N-acetylglucosamine and galactose residues.

Journal: Biochemistry 20010731

Title: Point mutations identified in Lec8 Chinese hamster ovary glycosylation mutants that inactivate both the UDP-galactose and CMP-sialic acid transporters.

Journal: The Journal of biological chemistry 20010713

Title: Redirection of sialic acid metabolism in genetically engineered Escherichia coli.

Journal: Glycobiology 20010701

Title: Exploring the acceptor substrate recognition of the human beta-galactoside alpha 2,6-sialyltransferase.

Journal: The Journal of biological chemistry 20010615

Title: Substrate recognition by UDP-galactose and CMP-sialic acid transporters. Different sets of transmembrane helices are utilized for the specific recognition of UDP-galactose and CMP-sialic acid.

Journal: The Journal of biological chemistry 20010615

Title: Soyasaponin I, a potent and specific sialyltransferase inhibitor.

Journal: Biochemical and biophysical research communications 20010608

Title: Dominant inheritance of sialuria, an inborn error of feedback inhibition.

Journal: American journal of human genetics 20010601

Title: Increased expression of UDP-galactose transporter messenger RNA in human colon cancer tissues and its implication in synthesis of Thomsen-Friedenreich antigen and sialyl Lewis A/X determinants.

Journal: Cancer research 20010601

Title: Sequence of the E. coli O104 antigen gene cluster and identification of O104 specific genes.

Journal: Gene 20010530

Title: Metabolic control of recombinant protein N-glycan processing in NS0 and CHO cells.

Journal: Biotechnology and bioengineering 20010505

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