Useful Method for Direct Introduction of the Photoaffinity 3-(4-Hydroxyphenyl)-3-trifluoromethyldiazirine Group

Abstract

A convergent and efficient preparation method of the photoaffinity 3-(4-alkoxyphenyl)-3-trifluoromethyldiazirine derivatives was established by direct introduction of the photoaffinity group utilizing the Mitsunobu reaction.

Design and Synthesis of a Tag‐Free Chemical Probe for Photoaffinity Labeling

“…The etherification was also possible under Mitsunobu conditions. [24] However, the yield was lower and separation of the byproducts turned out to be problematic. The final oxidation of the aldehyde 21 to the acid 22 was rather problematic.…”

Synthesis of photolabile .DELTA.lac-acetogenin for photoaffinity labeling of mitochondrial complex I

“…Pd(0)-catalyzed coupling of alkyne 10 with 3-bromo-2-propyn-1-ol gave 11 and subsequent hydrogenation with 10% Pd/C afforded 12. After the reaction of 12 with 3-(4-hydroxyphenyl)-3-trifluoromethyldiazirine, which was synthesized by the method of Lu et al, 12) under the Mitsunobu reaction conditions, 13) hydrolysis of the acetyl group and sequential deprotection of MOM ether afforded 13. The inhibition of complex I activity was determined by NADH oxidase assay using bovine heart submitochondrial particles.…”

Chemo-Enzymatic Synthesis of 1’-Photoreactive Sucrose Derivatives via Ether Linkage

“…The p-diazirinyl phenol 10 has been utilized to form ether linkage in the Mitsunobu reaction in previous reports. 18 The reported reaction was set at room temperature for all compounds with good yields. Our results indicated that Mitsunobu reaction of sucrose derivative 2 and diazirinyl phenols 9 or 10 were regulated by two factors.…”