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

Inspired by the multicomponent reaction-type scenario involving fatty dialdehydes, a nitrogen source, and acrolein, as a key C3 unit, put forward by Baldwin and Whitehead to explain the formation of manzamine-type alkaloids, 96 multicomponent reactions were designed, and their analytical readouts we...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 26; no. 11; pp. 2163 - 2168
Main Authors Leblond, Axel, Nguyen, Alexandre, Alcover, Charlotte, Leblanc, Karine, Gallard, Jean-François, Joseph, Delphine, Poupon, Erwan, Beniddir, Mehdi A.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.03.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BIOMIMETIC SYNTHESIS
AMPHIMEDON SP
MICHAEL
THROUGHPUT EXPERIMENTATION
CHEMISTRY
CATALYST
DISCOVERY
Online AccessGet full text

Cover

More Information
Summary:Inspired by the multicomponent reaction-type scenario involving fatty dialdehydes, a nitrogen source, and acrolein, as a key C3 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00194