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Updated: Jan 15, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

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ペプチド骨のリガンド制御型ステレオダイバーゲントα-ビニレーションおよびα-アリレーション

Jie Hu1, Shengjie Su1, Haodong Zhang1

  • 1Center for Supramolecular Chemistry and Catalysis, College of Sciences, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.

Journal of the American Chemical Society
|October 8, 2025
PubMed
まとめ

この研究は,ニッケル触媒によるクロスカップリングを用いてペプチドの骨組みを改変するための新しい方法を導入しています. このアプローチは,ペプチド化学における重要な合成障害を克服し,内部部位でのステレオ選択的機能化を可能にします.

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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