Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines
Tryptophan (Trp) carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification. Herein, we have reported a metal-free photoinduced N-H alkylation strategy using N-aryl glycines for specific modification of tryptophan-containing peptides. The robustnes...
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| Vydáno v: | Chinese chemical letters Ročník 35; číslo 6; s. 109244 - 319 |
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| Hlavní autoři: | , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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Elsevier B.V
01.06.2024
School of Medicine or Institute of Translation Medicine,Shanghai University,Shanghai 200444,China |
| Témata: | |
| ISSN: | 1001-8417, 1878-5964 |
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| Abstract | Tryptophan (Trp) carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification. Herein, we have reported a metal-free photoinduced N-H alkylation strategy using N-aryl glycines for specific modification of tryptophan-containing peptides. The robustness of our approach is demonstrated by its wide substrate scope, excellent isolated yields, as well as almost unobservable side effects. Using this highly efficiently metal-free condition, alkylated Trp-containing peptides can be smoothly assembled. This study provides a reliable and practical tool for the chemo-selective modification of various tryptophan containing oligopeptides.
Various alkylated Trp-containing peptides were synthesized by metal-free photoinduced decarboxylative alkylation in acceptable to excellent yields.
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| AbstractList | Tryptophan (Trp) carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification. Herein, we have reported a metal-free photoinduced N-H alkylation strategy using N-aryl glycines for specific modification of tryptophan-containing peptides. The robustness of our approach is demonstrated by its wide substrate scope, excellent isolated yields, as well as almost unobservable side effects. Using this highly efficiently metal-free condition, alkylated Trp-containing peptides can be smoothly assembled. This study provides a reliable and practical tool for the chemo-selective modification of various tryptophan containing oligopeptides.
Various alkylated Trp-containing peptides were synthesized by metal-free photoinduced decarboxylative alkylation in acceptable to excellent yields.
[Display omitted] Tryptophan(Trp)carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification.Herein,we have reported a metal-free photoinduced N-H alkylation strategy us-ing N-aryl glycines for specific modification of tryptophan-containing peptides.The robustness of our approach is demonstrated by its wide substrate scope,excellent isolated yields,as well as almost unob-servable side effects.Using this highly efficiently metal-free condition,alkylated Trp-containing peptides can be smoothly assembled.This study provides a reliable and practical tool for the chemo-selective modification of various tryptophan containing oligopeptides. |
| ArticleNumber | 109244 |
| Author | Liu, Chao Huang, Wenjing Gao, Fei Yin, Jianhui Hu, Honggang Guo, Changyong |
| AuthorAffiliation | School of Medicine or Institute of Translation Medicine,Shanghai University,Shanghai 200444,China |
| AuthorAffiliation_xml | – name: School of Medicine or Institute of Translation Medicine,Shanghai University,Shanghai 200444,China |
| Author_xml | – sequence: 1 givenname: Jianhui surname: Yin fullname: Yin, Jianhui – sequence: 2 givenname: Wenjing surname: Huang fullname: Huang, Wenjing – sequence: 3 givenname: Changyong surname: Guo fullname: Guo, Changyong – sequence: 4 givenname: Chao surname: Liu fullname: Liu, Chao – sequence: 5 givenname: Fei surname: Gao fullname: Gao, Fei email: Flyhightly@shu.edu.cn – sequence: 6 givenname: Honggang orcidid: 0000-0003-0577-3021 surname: Hu fullname: Hu, Honggang email: hhu66@shu.edu.cn |
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| Keywords | Tryptophan Modification Glycine Peptide Photoinduced |
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| Snippet | Tryptophan (Trp) carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification. Herein, we have reported a... Tryptophan(Trp)carries a unique heteroaromatic indole side chain and plays a critical role in peptide or protein modification.Herein,we have reported a... |
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| SubjectTerms | Glycine Modification Peptide Photoinduced Tryptophan |
| Title | Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines |
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