Effective Friedel-Crafts Acylation of Biotin Acid Chloride in Trifluoromethanesulfonic Acid

Yasuyuki MUTO; Yuta MURAI; Yasuko SAKIHAMA; Yasuyuki HASHIDOKO; Makoto HASHIMOTO

doi:10.1271/bbb.120553

Organic Chemistry Notes

Effective Friedel-Crafts Acylation of Biotin Acid Chloride in Trifluoromethanesulfonic Acid

Yasuyuki MUTO, Yuta MURAI, Yasuko SAKIHAMA, Yasuyuki HASHIDOKO, Makoto HASHIMOTO

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Keywords: biotin, avidin, Friedel-Crafts acylation, triflic acid, 2-(4'-hydroxyphenylazo)benzoic acid

JOURNAL FREE ACCESS

2012 Volume 76 Issue 11 Pages 2162-2164

DOI https://doi.org/10.1271/bbb.120553

View "Advance Publication" version (November 7, 2012).

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Abstract

Biotin is one of the most useful tags in (bio)analytical science due to its specific interaction with avidin, but is not easy to convert because of its low solubility in most solvents. Friedel-Crafts acylation of biotin acid chloride in triflic acid was examined, and the synthesized derivatives had stronger affinity to avidin than biotin in a binding assay using 2-(4'-hydroxyphenylazo)benzoic acid.

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