The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A

MJ Rodriguez, M Belvo, R Morris, DJ Zeckner…

Index: Rodriguez, Michael J.; Belvo, Matthew; Morris, Robert; Zeckner, Douglas J.; Current, William L.; Sachs, Roberta K.; Zweifel, Mark J. Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 2 p. 161 - 164

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Citation Number: 8

Abstract

The γ hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C′ provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical ...