The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-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) -lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (l'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 β-lactam precursors of carbapenem antibiotics / Bucciarclli, M.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 17(1999), pp. 2489-2494.

Enantioselective lipase-catalyzed acetylation of β-lactam precursors of carbapenem antibiotics

Davoli P.;Forni A.;Prati F.
1999

Abstract

The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-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) -lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (l'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.
1999
17
2489
2494
Enantioselective lipase-catalyzed acetylation of β-lactam precursors of carbapenem antibiotics / Bucciarclli, M.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 17(1999), pp. 2489-2494.
Bucciarclli, M.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1207270
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 12
social impact