Synthesis of a biotin-derived alkyne for pd-catalyzed coupling reactions.

[reaction: see text] An efficient synthesis of a terminal alkyne derived from d-biotin was developed to provide an alternative for carboxyl-based biotinylation. This approach was illustrated by the preparation of alkyne- and alkene-linked phenylalanine derivatives using palladium-catalyzed Sonogashira and Oh methodology. (Strept)avidin binding was observed using soluble and immobilized receptors. These results demonstrate the applicability of carbon-linked biotin derivatives for use in affinity-based purification and bioanalytical applications.