Pyruvate → 9-Azido-9-deoxy-N-acetylneuraminic acid

HRID 2211070Notes

Reaction equation

HRID 2211070 reaction equation
C(S)[C@@H](O)[C@H](O)CS.[C:9]([O-:14])(=[O:13])[C:10]([CH3:12])=[O:11].[N:15]([CH2:18][C@H:19]1[O:25][CH:23]([OH:24])[C@@H:22]([NH:26][C:27](=[O:29])[CH3:28])[C@@H:21]([OH:30])[C@@H:20]1[OH:31])=[N+:16]=[N-:17].OC(C1(O[C@@H]([C@@H]([C@@H](CO)O)O)[C@H](NC(C)=O)[C@@H](O)C1)O)=O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[N:15]([CH2:18][C@@H:19]([OH:25])[C@@H:20]([OH:31])[C@@H:21]1[O:30][C:10]([OH:11])([C:9](=[O:14])[OH:13])[CH2:12][C@H:23]([OH:24])[C@H:22]1[NH:26][C:27](=[O:29])[CH3:28])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 107735PyruvateHCID 439197N-Acetyl-Neuraminic AcidHCID 446094D-1,4-DithiothreitolHCID 117085726-azido-6-deoxy-N-acetylmannosamine

Product 1

HCID 154790309-Azido-9-deoxy-N-acetylneuraminic acidYield 84%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

In a 10 mL of 0.1M potassium phosphate buffer (pH 7.5) containing 10 mM DTT and 0.5M pyruvate were dissolved 50 mg of 6-azido-6-deoxy-N-acetylmannosamine and 1.5 mg of NeuAc aldolase. The starting material was consumed in 14 hours. The solution was lyophilized and the purification was carried out with Bio Gel P-2 gel filtration (3×90 cm) chromatography with a flow rate of 6 mL/40 minutes, at 4° C. The fractions containing the product were pooled and freezed dry to give Compound 203 in 84 percent yield.

Workup

  1. customThe starting material was consumed in 14 hours
  2. customthe purification
  3. filtrationwas carried out with Bio Gel P-2 gel filtration (3×90 cm) chromatography with a flow rate of 6 mL/40 minutes, at 4° C
  4. additionThe fractions containing the product
  5. customfreezed dry

Sources & evidence

ORD record
ord-c7625a1e51864332a731951bce9f5062
Source dataset
uspto-grants-1995_10
Patent number
US05461143

Reaction notes

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