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

ABSTRACT: [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.

SUBMITTER: Corona C

PROVIDER: S-EPMC2523258 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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

Corona Cesear C Bryant Bj K BK Arterburn Jeffrey B JB

Organic letters 20060401 9

[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- ...[more]

PMID: 16623575

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