Data di Pubblicazione:
1993
Citazione:
CHEMOENZYMATIC SYNTHESIS OF ACETYL (R)-(+)-CYCLOSERINE AND
(S)-(-)-CYCLOSERINE / M. De Amici, C. De Micheli, F. Cateni, G. Carrea, G. Ottolina. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 4:5(1993), pp. 1073-1080. [10.1016/S0957-4166(00)80156-1]
Abstract:
The two enantiomers of acetyl cycloserine 8, the immediate precursors of
the chiral forms of cycloserine 1, were prepared in enantiomeric excess
higher than 98\% by means of lipase-catalyzed hydrolysis of
3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the
five lipases tested, lipase from Chromobacterium viscosum was by far the
most selective catalyst. Since the enantiomeric ratio (E) of the
reaction was higher than 100, the hydrolysis spontaneously stopped at
50\% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline
{[(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate
[(S)-(-)-5] in almost enantiomerically pure form. Intermediates
(R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl
cycloserine through a four step sequence. This strategy constitutes a
valid alternative to the previously reported procedures.}
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. De Amici, C. De Micheli, F. Cateni, G. Carrea, G. Ottolina
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