Photodeprotection of up to Eight Photolabile Protecting Groups from a Single Glycan

Samarasimhareddy, Mamidi; Alshanski, Israel; Mervinetsky, Evgeniy; Hurevich, Mattan

doi:10.1055/s-0036-1591915

Cited by 5 publications

(2 citation statements)

References 5 publications

(4 reference statements)

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“…For over half a century, numerous studies have applied the ONB photoresponsive protecting group to control synthetic transformations, such as in peptide synthesis, , oligonucleotide synthesis, , glycoside synthesis, , and more. Moreover, the photoresponsive ortho -nitrobenzyl unit has been applied to develop a variety of technologies, including caged light-responsive ion carriers such as Ca 2+ and Mg 2+ ionophores and cryptands, photoresponsive polymer networks and photoresponsive hydrogels, , photoactivated prodrugs and drug delivery systems, photocaged bioconjugates, such as insulin, for controlled release, aggregation of nanoparticles, and surface patterning .…”

Section: Introductionmentioning

confidence: 99%

Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications

et al. 2023

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This review article introduces mechanistic aspects and applications of photochemically deprotected ortho-nitrobenzyl (ONB)-functionalized nucleic acids and their impact on diverse research fields including DNA nanotechnology and materials chemistry, biological chemistry, and systems chemistry. Specific topics addressed include the synthesis of the ONB-modified nucleic acids, the mechanisms involved in the photochemical deprotection of the ONB units, and the photophysical and chemical means to tune the irradiation wavelength required for the photodeprotection process. Principles to activate ONB-caged nanostructures, ONB-protected DNAzymes and aptamer frameworks are introduced. Specifically, the use of ONB-protected nucleic acids for the phototriggered spatiotemporal amplified sensing and imaging of intracellular mRNAs at the single-cell level are addressed, and control over transcription machineries, protein translation and spatiotemporal silencing of gene expression by ONB-deprotected nucleic acids are demonstrated. In addition, photodeprotection of ONB-modified nucleic acids finds important applications in controlling material properties and functions. These are introduced by the phototriggered fusion of ONB nucleic acid functionalized liposomes as models for cell–cell fusion, the light-stimulated fusion of ONB nucleic acid functionalized drug-loaded liposomes with cells for therapeutic applications, and the photolithographic patterning of ONB nucleic acid-modified interfaces. Particularly, the photolithographic control of the stiffness of membrane-like interfaces for the guided patterned growth of cells is realized. Moreover, ONB-functionalized microcapsules act as light-responsive carriers for the controlled release of drugs, and ONB-modified DNA origami frameworks act as mechanical devices or stimuli-responsive containments for the operation of DNA machineries such as the CRISPR-Cas9 system. The future challenges and potential applications of photoprotected DNA structures are discussed.

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Section: Introductionmentioning

confidence: 99%

Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications

et al. 2023

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“…The application of PPGs in the biological context dates back to the 1970s, to the first studies of Engels and Schlaeger and Kaplan et al with caged cAMP and ATP [10,11], following an earlier report by Barltrop and Schofield on the photorelease of glycine (Figure 2) [12]. Although the present paper will focus on the biological applications of PPGs, synthetic applications (although relatively less common in the literature vs. the biological ones) could also be envisaged [13,14]. A deprotection step carried out under mild conditions and not requiring an additional reagent (i.e., light acting as a traceless reagent) is of considerable interest also for designing a (more complex/multi-step) synthesis pathway.…”

Section: Introductionmentioning

confidence: 99%

Photoremovable Protecting Groups

Dunkel

2022

Encyclopedia

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Photoremovable protecting groups (PPGs) (also often called photocages in the literature) are used for temporary inactivation of biologically active substrates. By photoirradiation the PPG could be cleaved off and the biological activity could be restored on-demand, with a high spatiotemporal precision. The on-site liberation of the biologically active substrate could be exploited for studying dynamic biological processes or for designing targeted pharmacological interventions in vitro or in vivo. Several chemical scaffolds have been described and tested as PPGs, operating at different wavelengths. The scope of potential substrates is very broad, spanning from small molecules to proteins. In a wider context, PPGs could be used for the design of various light-responsive materials as well, for diverse applications.

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Photolabile Protecting Group‐Mediated Synthesis of 2‐Deoxy‐Glycosides

Liu

et al. 2021

Chin. J. Chem.

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Main observation and conclusion A green and efficient photolabile protecting group (PPG)‐mediated glycosidation approach for the synthesis of 2‐deoxy‐glycosides is reported. By employing ortho‐nitrobenzyl carbonate (oNBC) as PPG, N,N‐dimethylformamide (DMF)‐modulated SPhosAuNTf2‐promoted glycosidation with per‐oNBC‐protected 2‐deoxy‐glycosyl ynenoates affords the 2‐deoxy‐glycosides with moderate to excellent α‐selectivities presumably depending on the reactivities of the acceptor alcohols. Based on the PPG‐mediated glycosidation approach, oligosaccharides with three to six oNBC groups are effectively achieved. The multiple oNBC groups in the 2‐deoxy‐glycosides are completely cleaved by irradiation at 365 nm, resulting in the desired 2‐deoxy‐glycosides in an efficient manner without affecting the common alkyne, alkene, azide functional groups and the traditional protecting groups on the aglycones.

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Photodeprotection of up to Eight Photolabile Protecting Groups from a Single Glycan

Cited by 5 publications

References 5 publications

Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications

Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications

Photoremovable Protecting Groups

Photolabile Protecting Group‐Mediated Synthesis of 2‐Deoxy‐Glycosides

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