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Nonribosomal peptide cyclases possess enormous biocatalytic potential for cyclizing peptides, including those shorter than ten residues. However, N-acetylcysteamine (SNAC) or related low molecular weight thiol leaving groups, which have traditionally been used as surrogates for a pantetheine group on the substrate C-terminus, necessitate a labor-intensive process to prepare the substrate for cyclases. Our group recently established a faster, automation-compatible synthetic method for cyclase substrates, using ethylene glycol (EG) as a new pantetheine surrogate. This approach significantly streamlines substrate preparation while maintaining cyclization efficiency. In this chapter, we describe the synthetic pathway for the solid-phase peptide synthesis of EG-functionalized peptides, followed by enzymatic cyclization using nonribosomal peptide cyclases.

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Diol as a New Pantetheine Surrogate for Chemoenzymatic Synthesis of Cyclic Peptides via Nonribosomal Peptide Cyclases

  • 实验方案

  • 发表日期：

    2025年

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  • Kei Fujita,
  • Rintaro Ichihara,
  • Masakazu Kobayashi,
  • Kenichi Matsuda,
  • Toshiyuki Wakimoto

摘要

Nonribosomal peptide cyclases possess enormous biocatalytic potential for cyclizing peptides, including those shorter than ten residues. However, N-acetylcysteamine (SNAC) or related low molecular weight thiol leaving groups, which have traditionally been used as surrogates for a pantetheine group on the substrate C-terminus, necessitate a labor-intensive process to prepare the substrate for cyclases. Our group recently established a faster, automation-compatible synthetic method for cyclase substrates, using ethylene glycol (EG) as a new pantetheine surrogate. This approach significantly streamlines substrate preparation while maintaining cyclization efficiency. In this chapter, we describe the synthetic pathway for the solid-phase peptide synthesis of EG-functionalized peptides, followed by enzymatic cyclization using nonribosomal peptide cyclases.