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The breaking beads approach for photocleavage from solid support

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Abstract

Photocleavage from polystyrene beads is a pivotal reaction for solid phase synthesis that relies on photolabile linkers. Photocleavage from intact porous polystyrene beads is not optimal because light cannot penetrate into the beads and the surface area exposed to irradiation is limited. Thus, hazardous, technically challenging and expensive setups are used for photocleavage from intact beads. We developed a new concept in which grinding the beads during or prior to irradiation is employed as an essential part of the photocleavage process. By grinding the beads we are exposing more surface area to the light source, hence, photocleavage can be performed even using a simple benchtop LED setup. This approach proved very efficient for photocleavage of various model compounds including fully protected oligosaccharides.

Graphical abstract: The breaking beads approach for photocleavage from solid support

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Supplementary files

Article information


Submitted
20 Apr 2020
Accepted
13 May 2020
First published
13 May 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

The breaking beads approach for photocleavage from solid support

Y. Bakhatan, I. Alshanski, D. Grunhaus and M. Hurevich, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00821D

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