Linkers photolabile safety-catch

Routledge A, Abell C, Balasubramanian S. The use of a dithiane-protected benzoin photolabile safety catch linker for solid-phase synthesis. Tetrahedron Lett 1997 38 1227-1230. 

Cano, M., Ladlow, M. and Balasubramanian, S. (2002) Practical synthesis of a difhiane-protected 3, 5 -dialkoxybenzoin photolabile safety-catch linker for solid-phase organic synthesis. Journal of Organic Chemistry, 67,129-135. 

Felder ER, Petriella P, Schneider P, Synthesis of a photolabile safety catch linker of the 3 -methoxybenzoin type, Proc. of the First Int. Electr. Conf. on Synth. Org. Chem. (ECSOC-1), www.mdpi.org/ecsoc/, September 1-30, 1997. Poster http //www.unibas.ch/mdpi/ecsoc/b0003.html997. 

ER Felder, P Petriella, P Schneider. Synthesis of a photolabile safety catch linker of the 3 -methoxybenzoin type. First International Electronic Conference on Syn-... 

Routl997a Routledge, A., Abell, C. and Balasubramanian, S., The Use of a Dithiane Protected Benzoin Photolabile Safety Catch Linker for Solid-Phase Synthesis, Tetrahedron Lett., 38 (1997) 1227-1230. 

Recently, Belshaw [44] reported a safety-catch photolabile linker based on the phenacyl group that permits selective photorelease of oligonucleotides from a solid substrate. The safety-catch concept is based on masking the carbonyl group as a dimethyl ketal that renders the linker photoinert during oligonucleotide synthesis (Scheme 17.14). 

Scheme 17.14 Use of a safety-catch photolabile linker based on the phenacyl group for the selective photorelease of oligonucleotides.

An application of a related resin involves the synthesis of oligonucleotides via photolabile carbonate and carbamate anchors [230]. Photocleavable al-koxylbenzyl safety-catch solid supports Sr (Table 5) have been prepared [231,232]. Carboxylic acids were esterified by reaction with the secondary alcohol function of 5r and alcohols and amines could be attached via carbonate and carbamate derivatives, respectively. Unlike many previously reported photolabile linkers, these anchors were stable to irradiation with sunlight. In each case, product release was effected by treatment with mercuric chloride to remove the safety catch followed by irradiation with light of wavelength 350 nm, which leaves a benzofuran by-product tethered to the resin. 

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