Sodium Carbonate → Demannose

HRID 1740722Notes

Reaction equation

HRID 1740722 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C1C(N=C=S)=CC=C([O:16][CH:17]2[O:22][CH:21]([CH2:23][OH:24])[CH:20]([OH:25])[CH:19]([OH:26])[CH:18]2[OH:27])C=1>CN(C)C=O>[O:16]=[CH:17][C@H:18]([C@H:19]([C@@H:20]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:25])[OH:26])[OH:27]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 4182945beta-D-Galactopyranosylphenyl isothiocyanate

Product 1

HCID 161658Demannose

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthetic glycoprotein carriers were constructed in which poly(L-lysine), average chain length 100 (Mr 20,000 Da), was glycosylated using a-D-mannopyranosyl phenylisothiocyanate dissolved in N,N-dimethylformamide. The solution was adjusted to pH 9.5 by the addition of 1 M Sodium carbonate, pH 9.5. Shielded from light and incubated for 16 hours at 22° C., the solution was dialyzed against 5 mM Sodium chloride for two days. Approximately 0.8 to 1.0% of the amine side chains in the polylysine are glycosylated, as determined by absorbance spectroscopy at 250 nm. As a control, an alternative glycoprotein carrier was synthesized by substituting a-D-mannopyranosyl phenylisothiocyanate with a-D-galactopyranosyl phenylisothiocyanate.

Workup

  1. customthe solution was dialyzed against 5 mM Sodium chloride for two days
  2. customAs a control, an alternative glycoprotein carrier was synthesized

Sources & evidence

ORD record
ord-a89f975030674dfca6dfb0c2c08427dd
Source dataset
uspto-grants-1999_10
Patent number
US05972900

Reaction notes

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