Synthesis of Aminooxy and N-Alkylaminooxy Amines for Use in Bioconjugation

Five Boc-protected aminooxy and N-alkylaminooxy amines have been synthesized in 60−95% overall yield using a common synthetic strategy from readily available two- and three-carbon Cbz-protected amino alcohols. The amines can be linked to biomolecules via amide formation and incorporated directly int...

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Veröffentlicht in:	Journal of organic chemistry 2010-08, Vol.75 (16), p.5757-5759
Hauptverfasser:	Carrasco, Michael R, Alvarado, Carolina I, Dashner, Scott T, Wong, Amanda J, Wong, Michael A
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemical synthesis Amines - chemistry Chemistry Exact sciences and technology Ligands Molecular Structure Organic chemistry Peptides Peptoids - chemistry Preparations and properties Stereoisomerism
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creator	Carrasco, Michael R Alvarado, Carolina I Dashner, Scott T Wong, Amanda J Wong, Michael A
description	Five Boc-protected aminooxy and N-alkylaminooxy amines have been synthesized in 60−95% overall yield using a common synthetic strategy from readily available two- and three-carbon Cbz-protected amino alcohols. The amines can be linked to biomolecules via amide formation and incorporated directly into peptoids via submonomer synthesis. Subsequent deprotection of the aminooxy and N-alkylaminooxy groups enables conjugation with desired target molecules via established chemoselective ligation methods. The range of derivatives synthesized allows different distances to be established between the conjugated molecules.
doi_str_mv	10.1021/jo101066c
format	Article
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subjects	Amines - chemical synthesis Amines - chemistry Chemistry Exact sciences and technology Ligands Molecular Structure Organic chemistry Peptides Peptoids - chemistry Preparations and properties Stereoisomerism
title	Synthesis of Aminooxy and N-Alkylaminooxy Amines for Use in Bioconjugation
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