Synthesis of (2S,3R,4R)-Dihydroxyisoleucine for Use in Amatoxin Synthesis

被引：0

作者：

Chandra, Shambhu Deo ^{[1
]}

Gunasekera, Shanal ^{[1
]}

Noichl, Benjamin Philipp ^{[1
]}

Patrick, Brian O. ^{[1
]}

Perrin, David M. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

MANNICH-TYPE REACTIONS; RNA-POLYMERASE-II; ALPHA-AMANITIN; STRUCTURAL BASIS; TRANSCRIPTION; ACID; OXAZABOROLIDINES; INHIBITION; MECHANISM; PEPTIDES;

D O I：

10.1021/acs.joc.4c01051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a streamlined synthesis of (2S,3R,4R)-4,5-dihydroxy isoleucine (DHIle), an amino acid found in alpha-amanitin, which appears to be critical for toxicity. This synthetic route is transition metal-free and enables the production of significant quantities of DHIle with suitable protection for use in peptide synthesis. Its incorporation into a cytotoxic amatoxin analog is reported.

引用

页码：12739 / 12747

页数：9

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