N-protection of amino acid derivatives catalyzed by immobilized penicillin G acylase

Mergè Fité, Montserrat Capellas, M. Dolors Benaiges, Gloria Caminal, Pere Claṕes, Gregorio Alvaro

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10 Citations (Scopus)

Abstract

The introduction of a N-α-phenylacetyl moiety into glycine, methionine and aspartic acid derivatives using immobilized penicillin G acylase (PGA) as catalyst was studied. High synthetic yields (86-97%) were obtained in biphasic systems under thermodynamic control using fully carboxy-protected derivatives of amino acids such as H-Gly-OMe, H-Gly-OBzl, H-Met-OEt, H-Asp(OBut)-OMe, H-Asp(OMe)-OMe and H-Asp(OBzl)-OBzl. Moderate yields (50-62%) were obtained for the N-α protection of β-carboxy free, α-carboxy esters of aspartic acid such as H-Asp-OMe and H-Asp-OBzl in methanol/buffer mixtures under kinetic control. The synthesis of some phenylacetyl derivatives on a preparative scale under the optimum conditions is also described. © 1997 OPA (Overseas Publishers Association) Amsterdam B. V. Published in The Netherlands by Harwood Academic Publishers.
Original languageEnglish
Pages (from-to)317-332
JournalBiocatalysis and Biotransformation
Volume14
Issue number4
Publication statusPublished - 1 Dec 1997

Keywords

  • Diphasic system
  • Immobilized Penicillin G amidase
  • Mandelic acid
  • Monophasic system
  • N-phenylacetyl
  • N-Protection of amino acid derivatives
  • Phenylacetic acid

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