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Acrylamide → 5-N-Acetyl-9-O-acetyl-neuraminic acid

HRID 233548
Notes
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Reaction equation

HRID 233548 reaction equation
[C:1](OC[C@H]1OC(O)[C@@H](N)[C@@H](O)[C@@H]1O)(=[O:3])[CH3:2].[OH:16][C:17]([C:19]1([O:30][C@@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[C@H:24]([NH:25][C:26]([CH3:28])=[O:27])[C@@H:22]([OH:23])[CH2:21]1)[OH:20])=[O:18].C=CC(N)=O>P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(S)[C@@H](O)[C@H](O)CS.C([O-])(=O)C(C)=O.O>[C:1]([O:36][CH2:35][C@@H:33]([OH:34])[C@@H:31]([OH:32])[C@@H:29]1[O:30][C:19]([OH:20])([C:17](=[O:16])[OH:18])[CH2:21][C@H:22]([OH:23])[C@H:24]1[NH:25][C:26](=[O:27])[CH3:28])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 6579AcrylamideHCID 439197N-Acetyl-Neuraminic AcidHCID 131719162GlyTouCan:G81315WS

Product 1

HCID 920427445-N-Acetyl-9-O-acetyl-neuraminic acidYield 47%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent
HCID 62657
Potassium Phosphate, Tribasic
Solvent
HCID 107735PyruvateSolvent
HCID 446094D-1,4-DithiothreitolSolvent

Procedure

In a 10 mL of 0.1M potassium phosphate buffer (pH 7.5) were dissolved 10 mM DTT, 0.5M pyruvate, 100 mg of 6-O-acetylmannosamine, prepared as described above, and 1.5 mg NeuAc aldolase (36 U). The reaction mixture was incubated at 37° C. for 8 days followed by lyophilization. The lyophilized powder was dissolved in a small amount of water and directly applied to a Bio Gel P-2 column (3×90 cm) and eluted with a flow rate of 6 mL/40 minutes at 4° C. To remove the trace amount of contaminated NeuAc due to the hydrolysis of the product, another gel filtration was required. Compound 201 was obtained in 47 percent yield. Its physical data were consistent with the reported data.

Workup

  1. customprepared
  2. washeluted with a flow rate of 6 mL/40 minutes at 4° C
  3. customTo remove the trace amount of contaminated NeuAc due
  4. customto the hydrolysis of the product
  5. filtrationanother gel filtration

Sources & evidence

ORD record
ord-741cf5ac689a4803a5cf3c18601112e1
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05593887

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes