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.

References

Oct 25, 2000·Chemical & Pharmaceutical Bulletin·Y HidaiT Fukuyama
Nov 22, 2000·Biochimie·P EscoubasG Corzo
Nov 23, 2000·Journal of Medicinal Chemistry·K StrømgaardJ W Jaroszewski
Jun 30, 2004·Medicinal Research Reviews·Kristian Strømgaard, Ian Mellor
Feb 3, 2005·Toxicon : Official Journal of the International Society on Toxinology·Kristian StrømgaardStine B Vogensen
Apr 23, 2005·The Journal of Organic Chemistry·Marlen SchmidtGeorge Kokotos
Jun 29, 2005·Toxicon : Official Journal of the International Society on Toxinology·Manuel TzourosLaurent Bigler
Nov 23, 2005·Biochemistry·Tetsuya Kitaguchi, Kenton J Swartz
Sep 1, 2006·Journal of Medicinal Chemistry·Trine F AndersenKristian Strømgaard
Sep 11, 2009·The Journal of Organic Chemistry·Tina MittagTroels Skrydstrup
Nov 28, 2009·Journal of Mass Spectrometry : JMS·Silvan EichenbergerLaurent Bigler
Dec 30, 2010·Journal of Natural Products·Anne F BarslundKristian Strømgaard
Mar 8, 2011·Organic Letters·David SchaffertErnst Wagner
Aug 17, 2011·Biochemistry·Oleg I BaryginDenis B Tikhonov
Oct 29, 2011·Angewandte Chemie·Christian A OlsenKristian Strømgaard
Apr 11, 2012·The Journal of Organic Chemistry·Felix WojcikLaura Hartmann
Jul 12, 2013·European Journal of Mass Spectrometry·Manuel TzourosStefan Bienz

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Citations

Aug 17, 2020·Metabolites·Yvonne M ForsterLaurent Bigler

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