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 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.
Carrasco
Michael R
MR
Department of Chemistry and Biochemistry, Santa Clara University, 500 El Camino Real, Santa Clara, California 95053-0270, USA. mcarrasco@scu.edu
Alvarado
Carolina I
CI
Dashner
Scott T
ST
Wong
Amanda J
AJ
Wong
Michael A
MA
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D034444:Peptoids / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D008024:Ligands; D034444:Peptoids