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

Organic Letters
Cesear CoronaJeffrey B Arterburn

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.

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Citations

Mar 23, 2012·The Journal of Biological Chemistry·Tatiana P Soares da CostaAndrew D Abell
Nov 8, 2012·Bioscience, Biotechnology, and Biochemistry·Yasuyuki MutoMakoto Hashimoto
Oct 1, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paweł StrzelczykGrzegorz Bujacz
Mar 19, 2011·Chemistry, an Asian Journal·Tingyi LiJincheng Mao
Aug 11, 2018·Chemical Communications : Chem Comm·Le FangMichael Watkinson
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·José Carlos Iglesias-SánchezJosé Elguero
Oct 11, 2013·Organic & Biomolecular Chemistry·Anne I GermerothAlison N Hulme
Jan 15, 2021·Frontiers in Pharmacology·Ángela Martín-SerranoMaría I Montañez
Mar 28, 2017·Bioorganic & Medicinal Chemistry·Chintam Nagendra ReddyJoshua Rokach
Feb 20, 2007·Chemical Reviews·Rafael Chinchilla, Carmen Najera

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