Selective modification of tryptophan in polypeptides <i>via</i> C–N coupling with azoles using <i>in situ</i>-generated iodine-based oxidants in aqueous media-Reference-Cited by-同舟云学术

Selective modification of tryptophan in polypeptides via C–N coupling with azoles using in situ-generated iodine-based oxidants in aqueous media

Published:2023 Issue:87 Volume:59 Page:13026-13029
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Watanabe Shunsuke¹,Wada Yuki²,Kawano Masaki²^ORCID,Higashibayashi Shuhei¹^ORCID,Sugai Takeshi¹^ORCID,Hanaya Kengo¹^ORCID

Affiliation:

1. Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan

2. Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan

Abstract

Hypervalent iodine-mediated C–N coupling of the indole and azoles realizes the selective modification of tryptophan in polypeptides in aqueous media. The process allows the introduction of chemical handles and the peptide stapling.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2023/CC/D3CC03731B

Reference34 articles.

1. RNA-peptide fusions for the in vitro selection of peptides and proteins

2. Phage display: Concept, innovations, applications and future

3. Phage Display: Simple Evolution in a Petri Dish (Nobel Lecture)

4. A RaPID way to discover nonstandard macrocyclic peptide modulators of drug targets

5. Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation

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