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

Denise Pauli; Stefan Bienz

doi:10.1039/C5OB00108K

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

Denise Pauli^a and Stefan Bienz*^a

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^a Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland
E-mail: stefan.bienz@chem.uzh.ch
Tel: +41 (0)44 635 42 45

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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Publication details

The article was received on 19 Jan 2015, accepted on 26 Feb 2015 and first published on 03 Mar 2015

Article type: Paper

DOI: 10.1039/C5OB00108K

Author version available: Download Author version (PDF)

Citation: Org. Biomol. Chem., 2015,13, 4473-4485

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

D. Pauli and S. Bienz, Org. Biomol. Chem., 2015, 13, 4473
DOI: 10.1039/C5OB00108K
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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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