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.
Corona
Cesear
C
New Mexico State University, P.O. Box 30001MSC 3C, Las Cruces, New Mexico 88003, USA..
Bryant
Bj K
BK
Arterburn
Jeffrey B
JB
D000475:Alkenes / Q000138:chemical synthesis; D000480:Alkynes / Q000138:chemical synthesis*; D001360:Avidin / Q000737:chemistry; D001710:Biotin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D019921:Biotinylation; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D001360:Avidin; D010165:Palladium; D001710:Biotin