Sodium Hydroxide → HCID 102244862, compound

HRID 1779736Notes

Reaction equation

HRID 1779736 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([F:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[O:18].[Na+].[N-]=[N+]=[N-].[Na+].[OH-].[Na+].C(N[C@H]1[C@H]([C@@H]([C@@H](CO)O)O)OC(O)(C(=O)O)C[C@@H]1O)(=O)C>O>[C:1]([NH:4][C@H:5]1[C@H:11]([C@H:10]([F:13])[C@@H:9]([CH2:14][OH:15])[OH:8])[O:12][C:17]([OH:18])([C:16](=[O:21])[OH:20])[CH2:19][C@@H:6]1[OH:7])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 439197N-Acetyl-Neuraminic AcidHCID 10466144GlyTouCan:G32189XGHCID 23662274Sodium pyruvate

Product 1

HCID 102244862HCID 102244862, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

The compound (16) (1.241 g), sodium pyruvate (1.200 g) and sodium azide (4.3 mg) were dissolved in distilled water (4.3 ml) and the pH of the resulting solution was adjusted to 10.59 by 2N sodium hydroxide. To this solution, 4.3 mg (112 U) of N-acetyl-neuraminic acid aldolase (NAL-300, manufactured by Toyobo Co., Ltd.) was added, followed by stirring mildly at 20° C. for 4 days. Thereafter, the reaction solution was desalted with an ion exchange resin (Dowex 50X8-200, H-type) and purified by an ion exchange chromatography (Dowex 1, HCOOH-type; aqueous 1.0M-HCOOH solution) to give 0.342 g of the candy-like titled compound (yield: 19.2%).

Workup

  1. addition) was added
  2. custompurified by an ion exchange chromatography (Dowex 1, HCOOH-type; aqueous 1.0M-HCOOH solution)

Sources & evidence

ORD record
ord-0df27b14224c423386b818ef135089b4
Source dataset
uspto-grants-1997_05
Patent number
US05627290

Reaction notes

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