title: A stable bis-allyloxycarbonyl biotin aldehyde derivative for biotinylation via reductive alkylation: application to the synthesis of a biotinylated doxorubicin derivative.
abstract: A novel, stable, biotin aldehyde derivative is reported in which the biotin moiety is N1,N3-protected by the allyloxycarbonyl group. The derivative is stable to sodium cyanoborohydride mediated reductive alkylation and is cleaved under mild Pd [0] catalysis. This novel biotin aldehyde should have wide application in avidin- and streptavidin-based detection systems and bioassays. The derivative is utilized in the synthesis of a biotinylated doxorubicin analogue that retains topoisomerase activity.
authors.affiliation: The Wolfson Institute for Biomedical Research, University College London, The Cruciform Building, Gower Street, London, WC1E 6BT, United Kingdom.
authors.forename: Brigitte
authors.initials: B
authors.lastname: Allart
authors.forename: Pauliina
authors.initials: P
authors.lastname: Lehtolainen
authors.forename: Seppo
authors.initials: S
authors.lastname: Yla-Herttuala
authors.forename: John F
authors.initials: JF
authors.lastname: Martin
authors.forename: David L
authors.initials: DL
authors.lastname: Selwood
mesh_terms: D000345:Affinity Labels / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D019921:Biotinylation; D004250:DNA Topoisomerases, Type II / Q000187:drug effects; D004317:Doxorubicin / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000345:Affinity Labels; D000447:Aldehydes; D004317:Doxorubicin; D004250:DNA Topoisomerases, Type II