Issue 23, 2009
From the journal:

Chemical Communications

Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides†

Yuki Goto,ab   Kazuhiro Iwasaki,ac   Kohei Torikai,a   Hiroshi Murakamia  and  Hiroaki Suga*abc  

* Corresponding authors

a Research Center for Advanced Science and Technology, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904, Japan
E-mail: hsuga@rcast.u-tokyo.ac.jp
Fax: +81 3 5452 5495
Tel: +81 3 5452 5495

b Department of Advanced Interdisciplinary Studies, Graduate School of Engineering, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904, Japan

c Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904, Japan

Abstract

We report here the ribosomal synthesis of methyllanthionine-containing cyclic peptides involving a site-specific incorporation of vinylglycine under the reprogrammed genetic code, followed by the isomerization of the vinylglycine to dehydrobutyrine, and the subsequent intramolecular Michael addition of a cysteine residue placed at a downstream position of the vinylglycine.

Graphical abstract: Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides

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Article information

DOI
https://doi.org/10.1039/B904314D
Article type
Communication
Submitted
03 Mar 2009
Accepted
31 Mar 2009
First published
30 Apr 2009

Chem. Commun., 2009, 3419-3421

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Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides

Y. Goto, K. Iwasaki, K. Torikai, H. Murakami and H. Suga, Chem. Commun., 2009, 3419 DOI: 10.1039/B904314D

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