The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-β-lactams 3–6, useful precursors of carbapenem antibiotics, proceeds with high enantioselectivity (E > 98) to afford the corresponding acetates 3b–6b in optically pure form. The rate of acetylation is influenced by the relative stereochemistry of the C(3)–C(4) β-lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (1'R,3R) enantiomers, as determined by chemical correlation. On the other hand, the lipase-PS-catalyzed hydrolysis of esters 3b,d in phosphate buffer proceeds with low selectivity and at a lower rate.

Enantioselective Lipase-Catalyzed Acetylation of beta-Lactams Precursors of Carbapenem Antibiotics / Bucciarelli, Maria; Davoli, Paolo; Forni, Arrigo; Moretti, Irene; Prati, Fabio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - STAMPA. - 17:(1999), pp. 2489-2494.

Enantioselective Lipase-Catalyzed Acetylation of beta-Lactams Precursors of Carbapenem Antibiotics

BUCCIARELLI, Maria;DAVOLI, Paolo;FORNI, Arrigo;MORETTI, Irene;PRATI, Fabio
1999

Abstract

The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-β-lactams 3–6, useful precursors of carbapenem antibiotics, proceeds with high enantioselectivity (E > 98) to afford the corresponding acetates 3b–6b in optically pure form. The rate of acetylation is influenced by the relative stereochemistry of the C(3)–C(4) β-lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (1'R,3R) enantiomers, as determined by chemical correlation. On the other hand, the lipase-PS-catalyzed hydrolysis of esters 3b,d in phosphate buffer proceeds with low selectivity and at a lower rate.
17
2489
2494
Enantioselective Lipase-Catalyzed Acetylation of beta-Lactams Precursors of Carbapenem Antibiotics / Bucciarelli, Maria; Davoli, Paolo; Forni, Arrigo; Moretti, Irene; Prati, Fabio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - STAMPA. - 17:(1999), pp. 2489-2494.
Bucciarelli, Maria; Davoli, Paolo; Forni, Arrigo; Moretti, Irene; Prati, Fabio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/457172
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