Acetate → sodium [(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl] [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

HRID 532103

Reaction equation

HRID 532103 reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[CH:18][C:16]([NH2:17])=[N:15][C:13]2=[O:14])[C@H:9]([OH:20])[C@@H:8]1[OH:21])([OH:4])([OH:3])=[O:2].C(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O)(=O)C.C(O)(=O)C(C)=O.[Mg+2].[Cl-].[Cl-].O.P([O-])([O-])(OC(=O)C)=O.[OH-].[Na+:56].C([O-])(=O)C.[OH:61][C:62]([C:64]1([O:75][C@@H:74]([C@@H:76]([C@@H:78]([CH2:80][OH:81])[OH:79])[OH:77])[C@H:69]([NH:70][C:71]([CH3:73])=[O:72])[C@@H:67]([OH:68])[CH2:66]1)O)=[O:63].CC(N[C@H]1C([C@H](O)[C@H](O)CO)O[C@](OP(OC[C@H]2O[C@@H](N3C(=O)N=C(N)C=C3)[C@H](O)[C@@H]2O)([O-])=O)(C(O)=O)C[C@@H]1O)=O.[Na+]>C(O)C(N)(CO)CO.Cl>[CH3:73][C:71]([NH:70][C@H:69]1[C@H:74]([C@H:76]([OH:77])[C@H:78]([OH:79])[CH2:80][OH:81])[O:75][C@:64]([O:2][P:1]([O:5][CH2:6][C@H:7]2[O:11][C@@H:10]([N:12]3[C:13](=[O:14])[N:15]=[C:16]([NH2:17])[CH:18]=[CH:19]3)[CH:9]([OH:20])[C@H:8]2[OH:21])([O-:3])=[O:4])([C:62]([OH:63])=[O:61])[CH2:66][C@@H:67]1[OH:68])=[O:72].[Na+:56]

Participants

11

Reactant 9

HCID 175AcetateHCID 1060Pyruvic AcidHCID 61315'-Cytidylic acid2×HCID 14798Sodium HydroxideHCID 168060Magnesium chloride, monohydrateHCID 439174N-Acetyl-D-GlucosamineHCID 439197N-Acetyl-Neuraminic AcidHCID 4183249Acetic acid, monoanhydride with phosphoric acid, ion(2-)HCID 23679065CMP-NeuAc

Product 1

HCID 92132133sodium [(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl] [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

Reagents, catalysts & solvents 1

HCID 93573Tromethamine hydrochlorideSolvent

Procedure

A reaction mixture of 20-100 g of 20-80 mM cytidine 5′-monophosphate (CMP, Shanghai QZU Bioscience & Biotechnology), 34.15-136.6 g of 20-80 mM N-acetyl-D-glucosamine (Shanghai Jiubang Chemical), 33.9-101.7 g of 40-120 mM pyruvic acid, 30.9 g of 20 mM MgCl2.H2O (Duksan), 3.72 g of 1 mM CTP (Sigma), 84-525 g of 80-500 mM acetyl phosphate (Sigma) and 7 liters of 50 mM Tris HCl buffer (pH 7.0), maintained at pH 6.5-8.0 using 2M NaOH at 37° C., was mixed with the polymer beads prepared in Example 4, which have each of cytidine monophosphate kinase (CMK), acetate kinase (ACK), NeuAc aldolase (NAN), CMP-NeuAc synthetase (NEU) and GlcNAc-2-epimerase immobilized thereon. Then, the mixture was stirred in a reactor for 5-12 hours.

Workup

  1. temperaturemaintained at pH 6.5-8.0
  2. customat 37° C.
  3. additionwas mixed with the polymer
  4. custombeads prepared in Example 4, which

Sources & evidence

ORD record
ord-ad1d355cb08a4cfe91a8e816653fa2f5
Source dataset
uspto-grants-2014_10
Patent number
US08852891B2

Linked notes

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