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- W2004459035 abstract "Ausgehend von (S)-(+)-2-(Benzyloxy)[1-D1]ethanol (3) wurden (R)-(−)- und (S)-(+)-(Amino[2-D1]ethyl)phosphonsäure (8) synthetisiert. Der Enantiomerenüberschuß wurde mittels 1H-NMR-Spektroskopie nach Derivatisierung mit (+)-α-(Methoxy)-α-(trifluormethyl)phenylessigsäurechlorid bestimmt und beträgt 98%. Von Acanthamoeba castellanii werden diese zur (2-Amino-1-hydroxy[2-D1]ethyl)phosphonsäure (OH-AEP) (2-D1-2) hydroxyliert. Aus (S)-(+)-[2-D1]-AEP entsteht dabei (2S)-[2-D1]-OH-AEP, die auch aus [2,2-D2]-AEP neben [2,2-D2]-OH-AEP entsteht. Eine Aminotransferase tauscht somit teilweise das pro-R-Deuterium der [2,2-D2]-AEP gegen Wasserstoff aus. Biosynthesis of Natural Products with a P C Bond, IV. – Synthesis of (R)- and (S)-(2-Amino-[2-D1]ethyl)phosphonic Acid and Hydroxylation to (2-Amino-1-hydroxyethyl)phosphonic Acid in Acanthamoeba castellanii (Neff) Starting from (S)-(+)-2-(benzyloxy)[1-D1]ethanol (3), (R)-(−)-and (S)-(+)-(2-amino[2-D1]ethyl)phosphonic acid (8) are prepared. The enantiomeric excess as determined by 1H-NMR spectroscopy after derivatisation with (+)-α-(methoxy)-α-(trifluoromethyl)phenylacetyl chloride is 98%. These [2-D1]-AEP are hydroxylated by Acanthamoeba castellanii to give (2-amino-1-hydroxy[2-D1]ethyl)phosphonic acids (OH-AEP) (2-D1-2). (S)-(+)-[2-D1]-AEP is transformed into (2S)-[2-D1]-OH-AEP, also obtained from [2,2-D2]-AEP besides [2,2-D2]-OH-AEP. Therefore, the pro-R deuterium of [2,2-D2]-AEP is partly exchanged by an aminotransferase." @default.
- W2004459035 created "2016-06-24" @default.
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- W2004459035 date "1988-10-14" @default.
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- W2004459035 title "Biosynthese von Naturstoffen mit einer PC-Bindung, IV. Synthese der (R)- und (S)-(2-Amino[2-D1]ethyl)phosphonsäure und Hydroxylierung zu (2-Amino-1-hydroxyethyl)phosphonsäure inAcanthamoeba castellanii (Neff)" @default.
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- W2004459035 doi "https://doi.org/10.1002/jlac.198819881005" @default.
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