Enzymes in organic chemistry. Part 10:1 Chemo-enzymatic synthesis of L- phosphaserine and L-phosphaisoserine and enantioseparation of amino- hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

Friedrich Hammerschmidt, Wolfgang Lindner, Frank Wuggenig, Elfriede Zarbl

Veröffentlichungen: Beitrag in FachzeitschriftArtikelPeer Reviewed

Abstract

Diisopropyl 2-azido-1-acetoxyethylphosphonate (‘)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give a-hydroxyphosphonate (S)-(- )-6 and ester (R)-(-)-7, which was saponified to give (R)-(+)-6. The two a- hydroxyphosphonates (R)- and (S)-6 were transformed into l-phosphaisoserine and L-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. (C) 2000 Elsevier Science Ltd.
OriginalspracheEnglisch
Seiten (von - bis)2955-2964
Seitenumfang10
FachzeitschriftTetrahedron: Asymmetry
Jahrgang11
Ausgabenummer14
DOIs
PublikationsstatusVeröffentlicht - 2000

ÖFOS 2012

  • 1040 Chemie

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