Baldwin and Whitehead's Manzamine Alkaloids Biosynthesis Hypothesis Involves a Finely Tuned Reactivity of Acrolein: Automated Extraction of Reactivity Patterns from LC-MS2 Data

被引：0

作者：

Leblond, Axel ^{[1
]}

Nguyen, Alexandre ^{[1
]}

Alcover, Charlotte ^{[1
]}

Leblanc, Karine ^{[1
]}

Gallard, Jean-Francois ^{[2
]}

Joseph, Delphine ^{[1
]}

Poupon, Erwan ^{[1
]}

Beniddir, Mehdi A. ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, BioCIS, Chim Subst Nat, F-91400 Orsay, France

[2] Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 11期

关键词：

THROUGHPUT EXPERIMENTATION; BIOMIMETIC SYNTHESIS; AMPHIMEDON SP; DISCOVERY; MICHAEL; CHEMISTRY; CATALYST;

D O I：

10.1021/acs.orglett.4c00194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Inspired by the multicomponent reaction-type scenario involving fatty dialdehydes, a nitrogen source, and acrolein, as a key C-3 unit, put forward by Baldwin and Whitehead to explain the formation of manzamine-type alkaloids, 96 multicomponent reactions were designed, and their analytical readouts were deconvoluted using a herein-provided chemoinformatic workflow. This strategy pinpointed relevant conditions tuning the reactivity of acrolein to fulfill Baldwin and Whitehead's manzamine alkaloids biosynthetic hypothesis. This strategy can become part of a general method for the high-content analysis of multicomponent reactions applied to a natural product biosynthetic scenario.

引用

页码：2163 / 2168

页数：6