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

HRID 233556

Reaction equation

HRID 233556 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-20091454213a4006a46762a1aa23be0d
Source dataset
uspto-grants-1997_01
Patent number
US05593887

Linked notes

Loading…