Ribosomal synthesis of an amphotericin-B inspired macrocycle

Kohei Torikai, Hiroaki Suga

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Here we report in vitro ribosomal synthesis of a natural product-like macrocyclic peptide, inspired by the structure of amphotericin B (AmB), an amphiphilic and membrane-interacting antifungal natural product. This AmB-inspired macrocyclic peptide (AmP), one side of which is composed of hydrophobic terpene, and the other side comprises a peptidic chain, was synthesized utilizing flexizyme-assisted in vitro translation via an unusual but successful initiation with a d-cysteine derivative. The established method for the synthesis of AmPs is applicable to the generation of a diverse AmP library coupled with an in vitro display format, with the potential to lead to the discovery of artificial bioactive amphiphilic macrocycles.

Original languageEnglish
Pages (from-to)17359-17361
Number of pages3
JournalJournal of the American Chemical Society
Volume136
Issue number50
DOIs
Publication statusPublished - Dec 17 2014
Externally publishedYes

Fingerprint

Amphotericin B
Biological Products
Peptides
Peptide Library
Terpenes
Cysteine
Display devices
Derivatives
Membranes
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry
  • Medicine(all)

Cite this

Ribosomal synthesis of an amphotericin-B inspired macrocycle. / Torikai, Kohei; Suga, Hiroaki.

In: Journal of the American Chemical Society, Vol. 136, No. 50, 17.12.2014, p. 17359-17361.

Research output: Contribution to journalArticle

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