Nitrophenylgalactosides → (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 466505

Reaktionsgleichung

Reaktionsgleichung von HRID 466505
C1C=C([N+]([O-])=O)C([O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])=CC=1.C(=O)(O)[O-].[Na+]>>[O:10]=[CH:11][C@@H:12]([C@H:13]([C@H:14]([C@@H:15]([CH2:17][OH:18])[OH:16])[OH:19])[OH:20])[OH:21]

Komponenten

3

Edukt 2

HCID 96647NitrophenylgalactosidesHCID 516892Sodium Bicarbonate

Produkt 1

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

To a solution containing 30.12 g (100 mmol) o-nitrophenyl-β-D-galactoside in 1000 ml distilled water buffered at pH 6.8 with 0.5 M phosphate buffer and maintained at 37° C. is added 10 mg of monoclonal antibodies prepared according to Example 6. The reaction mixture is gently agitated for 2.0 hours. The monoclonal antibodies are then recovered from the reaction mixture by ultrafiltration. The filtrate is then cooled to 10° C. and treated with 9.2 g (110 mmol) sodium bicarbonate. The D-galactose is recovered by extracting the filtrate with three 100 ml portions of diethyl ether. The ether portions are combined, washed once with 1.0 N sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield D-galactose. The aqueous portion is then combined with the sodium bicarbonate wash and acidified to pH 3 by the addition of 5 N hydrochloric acid. The acidified aqueous portion is then extracted three times with ether. The etheral extracts are combined, dried over magnesium sulfate, filtered and concentrated at reduced pressure to yield o-nitrophenol. The o-nitrophenol and D-galactose may be further purified by HPLC or by recrystallization.

Aufarbeitung

  1. distillationdistilled water
  2. additionis added 10 mg of monoclonal antibodies
  3. customprepared
  4. filtrationThe monoclonal antibodies are then recovered from the reaction mixture by ultrafiltration
  5. temperatureThe filtrate is then cooled to 10° C.
  6. customThe D-galactose is recovered
  7. extractionby extracting the filtrate with three 100 ml portions of diethyl ether
  8. washwashed once with 1.0 N sodium bicarbonate
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d2101e9e411a46579f2a472913ec8f7c
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05156965

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