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


Pauli, Denise; Bienz, Stefan (2015). Regioselective solid-phase synthesis of N-monohydroxylated and N-mono-methylated acylpolyamine spider toxins using an 2-(orthonitrophenyl)ethanal-modified resin. Organic & Biomolecular Chemistry, 13:4473-4485.

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:26 February 2015
Deposited On:18 Dec 2015 08:00
Last Modified:05 Apr 2016 19:12
Publisher:RSC Publishing
ISSN:1477-0520
Publisher DOI:https://doi.org/10.1039/c5ob00108k

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