Abstract
Light-triggered chemical reactions can provide excellent tools to investigate the fundamental mechanisms important in biology. Light is easily applicable and orthogonal to most cellular events, and its dose and locality can be controlled in tissues and cells. Light-induced conversion of photochemical groups installed on small molecules, proteins, and oligonucleotides can alter their functional states and thus the ensuing biological events. Recently, photochemical control of DNA/RNA structure and function has garnered attention thanks to the rapidly expanding photochemistry used in diverse biological applications. Photoconvertible groups can be incorporated in the backbone, ribose, and nucleobase of an oligonucleotide to undergo various irreversible and reversible light-induced reactions such as cleavage, crosslinking, isomerization, and intramolecular cyclization reactions. In this review, we gather a list of photoconvertible groups used in oligonucleotides and summarize their reaction characteristics, impacts on DNA/RNA thermal stability and structure, as well as their biological applications.
Highlights
Biological applications. pHP modi cations were shown to temporarily block the antisense pairing between non-coding RNAs catalyzed by the RNA chaperone Hfq[62] and to regulate the function of the twister ribozyme.[73,74]
The photochromism of the modi ed dU with 2-Py or PhtBu was maintained in the environment of the single-stranded oligonucleotide, and for PhtBu even in the duplex
Signi cant strides have been made in the availability and applicability of photoreactive oligonucleotides
Summary
Optical control of chemical reactions has recently gained popularity.[1,2,3,4] These controls rely on photoconvertible groups. PHP modi cations were shown to temporarily block the antisense pairing between non-coding RNAs catalyzed by the RNA chaperone Hfq[62] and to regulate the function of the twister ribozyme.[73,74] The fast uncaging of pHP and its derivatives could be promising for various timeresolved studies that require the photoremoval reaction to occur faster than the molecular process under investigation.[73] phosphorothioate DNA.[28] Upon light irradiation, TEEP–OH is photocleaved and the phosphate backbone reverts to its native form (Fig. 4). Such inhibition of RNA folding could be abolished upon the photocleavage of ArS.[78]
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