Photolabile Linkers for Solid-Phase Synthesis

Remi J.T. Mikkelsen; Katja E. Grier; Kim T. Mortensen; Thomas E. Nielsen; Katrine Qvortrup

doi:10.1021/acscombsci.8b00028

Photolabile Linkers for Solid-Phase Synthesis

Remi J.T. Mikkelsen, Katja E. Grier, Kim T. Mortensen, Thomas E. Nielsen^*, Katrine Qvortrup

^*Corresponding author for this work

15 Citations (Scopus)

Abstract

Photolabile linkers are the subjects of intense research because they allow the release of the target molecule simply by irradiation. Photochemical release of synthesis products is often facilitated without additional reagents under mild reaction conditions, which may even be environmentally friendly and appealing in the context of greener chemistry. The mild conditions also allow for applications of released material in subsequent biological screening experiments, where contamination with cleavage reagents would be detrimental. This Review pays attention to the increasing number of photolabile linkers developed for solid-phase synthesis and release and covers: (i) o-nitrobenzyloxy linkers, (ii) o-nitrobenzylamino linkers, (iii) α-substituted o-nitrobenzyl linkers, (iv) o-nitroveratryl linkers, (v) phenacyl linkers, (vi) p-alkoxyphenacyl linkers, (vii) benzoin linkers, (viii) pivaloyl linkers, and (ix) other photolabile linkers.

Original language	English
Journal	ACS Combinatorial Science
Volume	20
Issue number	7
Pages (from-to)	377-379
Number of pages	3
ISSN	2156-8952
DOIs	https://doi.org/10.1021/acscombsci.8b00028
Publication status	Published - 2018

Keywords

chemical biology
combinatorial chemistry
photolabile linker
solid-phase synthesis

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10.1021/acscombsci.8b00028

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title = "Photolabile Linkers for Solid-Phase Synthesis",

abstract = "Photolabile linkers are the subjects of intense research because they allow the release of the target molecule simply by irradiation. Photochemical release of synthesis products is often facilitated without additional reagents under mild reaction conditions, which may even be environmentally friendly and appealing in the context of greener chemistry. The mild conditions also allow for applications of released material in subsequent biological screening experiments, where contamination with cleavage reagents would be detrimental. This Review pays attention to the increasing number of photolabile linkers developed for solid-phase synthesis and release and covers: (i) o-nitrobenzyloxy linkers, (ii) o-nitrobenzylamino linkers, (iii) α-substituted o-nitrobenzyl linkers, (iv) o-nitroveratryl linkers, (v) phenacyl linkers, (vi) p-alkoxyphenacyl linkers, (vii) benzoin linkers, (viii) pivaloyl linkers, and (ix) other photolabile linkers.",

keywords = "chemical biology, combinatorial chemistry, photolabile linker, solid-phase synthesis",

author = "Mikkelsen, {Remi J.T.} and Grier, {Katja E.} and Mortensen, {Kim T.} and Nielsen, {Thomas E.} and Katrine Qvortrup",

year = "2018",

doi = "10.1021/acscombsci.8b00028",

language = "English",

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T1 - Photolabile Linkers for Solid-Phase Synthesis

AU - Mikkelsen, Remi J.T.

AU - Grier, Katja E.

AU - Mortensen, Kim T.

AU - Nielsen, Thomas E.

AU - Qvortrup, Katrine

PY - 2018

Y1 - 2018

N2 - Photolabile linkers are the subjects of intense research because they allow the release of the target molecule simply by irradiation. Photochemical release of synthesis products is often facilitated without additional reagents under mild reaction conditions, which may even be environmentally friendly and appealing in the context of greener chemistry. The mild conditions also allow for applications of released material in subsequent biological screening experiments, where contamination with cleavage reagents would be detrimental. This Review pays attention to the increasing number of photolabile linkers developed for solid-phase synthesis and release and covers: (i) o-nitrobenzyloxy linkers, (ii) o-nitrobenzylamino linkers, (iii) α-substituted o-nitrobenzyl linkers, (iv) o-nitroveratryl linkers, (v) phenacyl linkers, (vi) p-alkoxyphenacyl linkers, (vii) benzoin linkers, (viii) pivaloyl linkers, and (ix) other photolabile linkers.

AB - Photolabile linkers are the subjects of intense research because they allow the release of the target molecule simply by irradiation. Photochemical release of synthesis products is often facilitated without additional reagents under mild reaction conditions, which may even be environmentally friendly and appealing in the context of greener chemistry. The mild conditions also allow for applications of released material in subsequent biological screening experiments, where contamination with cleavage reagents would be detrimental. This Review pays attention to the increasing number of photolabile linkers developed for solid-phase synthesis and release and covers: (i) o-nitrobenzyloxy linkers, (ii) o-nitrobenzylamino linkers, (iii) α-substituted o-nitrobenzyl linkers, (iv) o-nitroveratryl linkers, (v) phenacyl linkers, (vi) p-alkoxyphenacyl linkers, (vii) benzoin linkers, (viii) pivaloyl linkers, and (ix) other photolabile linkers.

KW - chemical biology

KW - combinatorial chemistry

KW - photolabile linker

KW - solid-phase synthesis

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DO - 10.1021/acscombsci.8b00028

M3 - Review

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SN - 2156-8952

VL - 20

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EP - 379

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

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ER -

Photolabile Linkers for Solid-Phase Synthesis

Abstract

Keywords

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