A stable bis-allyloxycarbonyl biotin aldehyde derivative for biotinylation via reductive alkylation: application to the synthesis of a biotinylated doxorubicin derivative.
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.
Allart
Brigitte
B
The Wolfson Institute for Biomedical Research, University College London, The Cruciform Building, Gower Street, London, WC1E 6BT, United Kingdom.
Lehtolainen
Pauliina
P
Yla-Herttuala
Seppo
S
Martin
John F
JF
Selwood
David L
DL
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
D000345:Affinity Labels; D000447:Aldehydes; D004317:Doxorubicin; D004250:DNA Topoisomerases, Type II