Z-Ala-gln-OH → L-Alanyl-L-Glutamine

HRID 1086941

Reaktionsgleichung

Reaktionsgleichung von HRID 1086941
C([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][C:20](=[O:22])[NH2:21])=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.[H][H]>CO.O.[C].[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][C:20](=[O:22])[NH2:21])=[O:15])[CH3:13]

Komponenten

6

Edukt 2

HCID 14534789Z-Ala-gln-OHHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 123935L-Alanyl-L-GlutamineAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 200 ml three-necked flask was charged 5.0 g (14.2 mmol) of Z-L-Ala-L-Gln, and the peptide was dissolved in 100 ml of a mixture of methanol and water (methanol:water =7:3) and stirred with a magnetic stirrer. After the air in the flask had been replaced with nitrogen, 0.8 g of 2% by weight of palladium-carbon was added thereto, and the protective group was eliminated in a stream of hydrogen. After 2 hours, the completion of the reaction was confirmed by thin layer chromatography, and then the palladium-carbon was filtered off. The filtrate was concentrated to 20 ml under reduced pressure, and 40 ml of isopropyl alcohol was added thereto. The resulting mixture was stirred for 30 minutes, during which time crystals precipitated. The crystals were collected by filtration, washed with isopropyl alcohol and then dried under reduced pressure to give 2.8 g (12.9 mmol) (90%) of L-Ala-L-Gln.

Aufarbeitung

  1. additionwas added
  2. filtrationthe palladium-carbon was filtered off
  3. concentrationThe filtrate was concentrated to 20 ml under reduced pressure, and 40 ml of isopropyl alcohol
  4. additionwas added
  5. stirringThe resulting mixture was stirred for 30 minutes, during which time crystals
  6. customprecipitated
  7. filtrationThe crystals were collected by filtration
  8. washwashed with isopropyl alcohol
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60edb0568624431aa3dd8c20db345199
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05032675

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