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Paper | Special issue | Vol 30, No. 2, 1990, pp.909-927
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S84
Concerning the Intermediacy of Monocyclic β-Lactams in Penicillin Biosynthesis: Synthesis and Attempted Bioconversion of Seco-isopenicillin N

A. Ian Scott,* Ramaswamy Shankaranarayan, and Sung-Kee Chung

*Center for Biological NMR, Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, U.S.A.

Abstract

The title compound (3a) was synthesized as its dimer by the skeletal rearrangement of protected isopenicillin N-sulfoxide, hydrogenation, hydrolysis of the thiazoline ring, oxidative dimerization and deprotection. The reductive conversion of the dimer to monomer (3a) was clearly demonstrated. Seco-isopenicillin N (3a) gave no bioactive products on incubation with cell-free systems from either Cephalosporium acremonium or Streptomyces clavuligerus.