Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:17])[C@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:17])[C@@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of (±)-α-methyltryptophan methyl ester (150.0 mg, 0.646 mmol) in 50 mL of 50 mM sodium phosphate buffer pH 7.5 was added carboxypeptidase Y from Bakers Yeast (6.4 mg). The resulting suspension was stirred at ambient temperature. After 4 h, 75% conversion was observed by HPLC (C18 column, 254 nm detection, acid tR =9.0 min and ester tR =11.9 min). The reaction was extracted with 2×25 mL chloroform. The combined extracts were treated with brine, dried with magnesium sulfate, then concentrated in vacuo to yield (R)-α-methyltryptophan methyl ester (15.6 mg, 67.2 mmol, 10.4%). A portion of this α-methyl amino ester was derivatized with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (TAGIT). HPLC analysis of the resulting thioureas showed the (R,S)-diastereomer to be in >99% diastereomeric excess (C18 column, 254 nm detection, S,S)-diastereomer tR =15.9 min and (R,S)-diastereomer tR =16.8 min).
Aufarbeitung
- additionwas added carboxypeptidase Y from Bakers Yeast (6.4 mg)
- extractionThe reaction was extracted with 2×25 mL chloroform
- additionThe combined extracts were treated with brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-9c71beaed8264b348facb4cab7b20ba6
- Quelldatensatz
- uspto-grants-1996_02
- Patentnummer
- US05492830
Verknüpfte Notizen
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