Regioselective solid-phase synthesis of N-mono-hydroxylated and N-mono-methylated acylpolyamine spider toxins using an 2-(ortho-nitrophenyl)ethanal-modified resin

Organic & Biomolecular Chemistry
Denise Pauli, Stefan Bienz

Abstract

A recently introduced new SPS resin, possessing a 2-(ortho-nitrophenyl)ethanal linker, was used for the regioselective on-resin synthesis of N-mono-hydroxylated and N-mono-methylated polyamine spider toxins of Agelenopsis aperta and Larinioides folium. The polyamine backbones of the target compounds were efficiently constructed from the center by reductive amination of the aldehyde linker, followed by stepwise alkylation and acylation on solid support. Depending on the cleavage conditions, employing either oxidation/Cope elimination or methylation/Hofmann elimination, regioselectively the respective N-hydroxyl or N-methyl products were obtained. Employing this methodology, a number of acylpolyamine spider toxins were synthesized and identified as venom components by UHPLC and ESI-MS/MS.

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Citations

Aug 17, 2020·Metabolites·Yvonne M ForsterLaurent Bigler

Related Concepts

Oxidation
Polyamines
Scorpion Venoms
Mass Spectrometry
2-nitrophenyl-beta-D-glucopyranoside
Acetylspermidine deacetylase
Amine Test
Health Center
AS resin
Hydroxyl group

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