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肽模拟物的可持续合成——化学酶串联氧化-Ugi反应。

The sustainable synthesis of peptidomimetics chemoenzymatic tandem oxidation-Ugi reaction.

作者信息

Madej Arleta, Koszelewski Dominik, Paprocki Daniel, Brodzka Anna, Ostaszewski Ryszard

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52 01-224 Warsaw Poland

出版信息

RSC Adv. 2018 Aug 8;8(50):28405-28413. doi: 10.1039/c8ra04583f. eCollection 2018 Aug 7.

DOI:10.1039/c8ra04583f
PMID:35542459
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9084175/
Abstract

A simply and green synthetic protocol based on the selective laccase-oxidation of alcohol to a corresponding aldehyde and a following Ugi reaction in a micellar system made of SDS was developed and is reported herein. Special emphasis was placed on the metal-free chemoenzymatic tandem reaction based on alcohol oxidation strategies using molecular oxygen from air, followed by an Ugi reaction. The reaction was carried out without the use of a transition metal or organic solvents as a reaction medium. The presented protocol offers an efficient and environmentally friendly procedure.

摘要

本文报道了一种简单且绿色的合成方法,该方法基于在由十二烷基硫酸钠(SDS)制成的胶束体系中,通过漆酶将醇选择性氧化为相应的醛,随后进行Ugi反应。特别强调了基于使用空气中的分子氧的醇氧化策略的无金属化学酶串联反应,随后是Ugi反应。该反应在不使用过渡金属或有机溶剂作为反应介质的情况下进行。所提出的方法提供了一种高效且环境友好的程序。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/10eaae67039c/c8ra04583f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/442d6ab34a37/c8ra04583f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/906f2a68f62d/c8ra04583f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/84d600229128/c8ra04583f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/10eaae67039c/c8ra04583f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/442d6ab34a37/c8ra04583f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/906f2a68f62d/c8ra04583f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/84d600229128/c8ra04583f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c4ec/9084175/10eaae67039c/c8ra04583f-f2.jpg

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本文引用的文献

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Ugi multicomponent reaction product: the inhibitive effect on DNA oxidation depends upon the isocyanide moiety.Ugi 多组分反应产物:异氰基部分对 DNA 氧化的抑制作用取决于异氰基部分。
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醇的 Ugi 四组分反应:化学计量和催化氧化/MCR 序列。
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Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols.通过与伯醇的催化脱氢偶联进行单瓶合成N-酰化吲哚。
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