@article{govan_young_lively_deiters_2015, title={Optically triggered immune response through photocaged oligonucleotides}, volume={56}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2015.01.165}, abstractNote={Bacterial and viral CpG oligonculeotides are unmethylated cytosine-phosphate-guanosine dinucleotide sequences and trigger an innate immune response through activation of the toll-like receptor 9 (TLR9). We have developed synthetic photocaged CpGs via site-specific incorporation of nitropiperonyloxymethyl (NPOM)-caged thymidine residues. These oligonucleotides enable the optical control of TLR9 function and thereby provide light-activation of an immune response. We provide a proof-of-concept model by applying a reporter assay in live cells and by quantification of endogenous production of interleukin 6.}, number={23}, journal={TETRAHEDRON LETTERS}, author={Govan, Jeane M. and Young, Douglas D. and Lively, Mark O. and Deiters, Alexander}, year={2015}, month={Jun}, pages={3639–3642} }
 @article{dush_mciver_parr_young_fisher_newman_sannes_hauck_deiters_nascone-yoder_2011, title={Heterotaxin: A TGF-beta Signaling Inhibitor Identified in a Multi-Phenotype Profiling Screen in Xenopus Embryos}, volume={18}, ISSN={["1879-1301"]}, DOI={10.1016/j.chembiol.2010.12.008}, abstractNote={Disruptions of anatomical left-right asymmetry result in life-threatening heterotaxic birth defects in vital organs. We performed a small molecule screen for left-right asymmetry phenotypes in Xenopus embryos and discovered a pyridine analog, heterotaxin, which disrupts both cardiovascular and digestive organ laterality and inhibits TGF-β-dependent left-right asymmetric gene expression. Heterotaxin analogs also perturb vascular development, melanogenesis, cell migration, and adhesion, and indirectly inhibit the phosphorylation of an intracellular mediator of TGF-β signaling. This combined phenotypic profile identifies these compounds as a class of TGF-β signaling inhibitors. Notably, heterotaxin analogs also possess highly desirable antitumor properties, inhibiting epithelial-mesenchymal transition, angiogenesis, and tumor cell proliferation in mammalian systems. Our results suggest that assessing multiple organ, tissue, cellular, and molecular parameters in a whole organism context is a valuable strategy for identifying the mechanism of action of bioactive compounds.}, number={2}, journal={CHEMISTRY & BIOLOGY}, author={Dush, Michael K. and McIver, Andrew L. and Parr, Meredith A. and Young, Douglas D. and Fisher, Julie and Newman, Donna R. and Sannes, Philip L. and Hauck, Marlene L. and Deiters, Alexander and Nascone-Yoder, Nanette}, year={2011}, month={Feb}, pages={252–263} }
 @article{karginov_zou_shirvanyants_kota_dokholyan_young_hahn_deiters_2011, title={Light Regulation of Protein Dimerization and Kinase Activity in Living Cells Using Photocaged Rapamycin and Engineered FKBP}, volume={133}, ISSN={["0002-7863"]}, DOI={10.1021/ja109630v}, abstractNote={We developed a new system for light-induced protein dimerization in living cells using a photocaged analogue of rapamycin together with an engineered rapamycin binding domain. Using focal adhesion kinase as a target, we demonstrated successful light-mediated regulation of protein interaction and localization in living cells. Modification of this approach enabled light-triggered activation of a protein kinase and initiation of kinase-induced phenotypic changes in vivo.}, number={3}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Karginov, Andrei V. and Zou, Yan and Shirvanyants, David and Kota, Pradeep and Dokholyan, Nikolay V. and Young, Douglas D. and Hahn, Klaus M. and Deiters, Alexander}, year={2011}, month={Jan}, pages={420–423} }
 @article{young_lively_deiters_2010, title={Activation and Deactivation of DNAzyme and Antisense Function with Light for the Photochemical Regulation of Gene Expression in Mammalian Cells}, volume={132}, ISSN={["1520-5126"]}, DOI={10.1021/ja100710j}, abstractNote={The photochemical regulation of biological systems represents a very precise means of achieving high-resolution control over gene expression in both a spatial and a temporal fashion. DNAzymes are enzymatically active deoxyoligonucleotides that enable the site-specific cleavage of RNA and have been used in a variety of in vitro applications. We have previously reported the photochemical activation of DNAzymes and antisense agents through the preparation of a caged DNA phosphoramidite and its site-specific incorporation into oligonucleotides. The presence of the caging group disrupts either DNA:RNA hybridization or catalytic activity until removed via a brief irradiation with UV light. Here, we are expanding this concept by investigating the photochemical deactivation of DNAzymes and antisense agents. Moreover, we report the application of light-activated and light-deactivated antisense agents to the regulation of gene function in mammalian cells. This represents the first example of gene silencing antisense agents that can be turned on and turned off in mammalian tissue culture.}, number={17}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Young, Douglas D. and Lively, Mark O. and Deiters, Alexander}, year={2010}, month={May}, pages={6183–6193} }
 @article{chou_young_deiters_2010, title={Photocaged T7 RNA Polymerase for the Light Activation of Transcription and Gene Function in Pro- and Eukaryotic Cells}, volume={11}, ISSN={["1439-7633"]}, DOI={10.1002/cbic.201000041}, abstractNote={Abstract}, number={7}, journal={CHEMBIOCHEM}, author={Chou, Chungjung and Young, Douglas D. and Deiters, Alexander}, year={2010}, month={May}, pages={972–977} }
 @article{wilkins_marionni_young_liu_wang_di salvo_deiters_cropp_2010, title={Site-Specific Incorporation of Fluorotyrosines into Proteins in Escherichia coli by Photochemical Disguise}, volume={49}, ISSN={["0006-2960"]}, DOI={10.1021/bi100013s}, abstractNote={Fluorinated analogues of tyrosine can be used to manipulate the electronic environments of protein active sites. The ability to selectively mutate tyrosine residues to fluorotyrosines is limited, however, and can currently only be achieved through the total synthesis of proteins. As a general solution to this problem, we genetically encoded the unnatural amino acids o-nitrobenzyl-2-fluorotyrosine, -3-fluorotyrosine, and -2,6-difluorotyrosine in Escherichia coli. These amino acids are disguised from recognition by the endogenous protein biosynthetic machinery, effectively preventing global incorporation of fluorotyrosine into proteins.}, number={8}, journal={BIOCHEMISTRY}, author={Wilkins, Bryan J. and Marionni, Samuel and Young, Douglas D. and Liu, Jia and Wang, Yan and Di Salvo, Martino L. and Deiters, Alexander and Cropp, T. Ashton}, year={2010}, month={Mar}, pages={1557–1559} }
 @article{young_connelly_grohmann_deiters_2010, title={Small Molecule Modifiers of MicroRNA miR-122 Function for the Treatment of Hepatitis C Virus Infection and Hepatocellular Carcinoma}, volume={132}, ISSN={["1520-5126"]}, DOI={10.1021/ja910275u}, abstractNote={MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation has the potential to provide new therapeutic approaches to such diseases. Here, we report the first small molecule inhibitors and activators of the liver-specific microRNA miR-122. This microRNA is the most abundant microRNA in the liver and is involved in hepatocellular carcinoma development and hepatitis C virus (HCV) infection. Our small molecule inhibitors reduce viral replication in liver cells and represent a new approach to the treatment of HCV infections. Moreover, small molecule activation of miR-122 in liver cancer cells selectively induced apoptosis through caspase activation, thus having implications in cancer chemotherapy. In addition to providing a new approach for the development of therapeutics, small molecule modifiers of miR-122 function are unique tools for exploring miR-122 biogenesis.}, number={23}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Young, Douglas D. and Connelly, Colleen M. and Grohmann, Christoph and Deiters, Alexander}, year={2010}, month={Jun}, pages={7976–7981} }
 @article{chou_young_deiters_2009, title={A Light-Activated DNA Polymerase}, volume={48}, ISSN={["1521-3773"]}, DOI={10.1002/anie.200901115}, abstractNote={When the time is right: The widely applied Thermus aquaticus DNA polymerase was rendered light-activatable by incorporation of the photocaged amino acid ortho-nitrobenzyl tyrosine in place of a key tyrosine residue in the active site (see picture). As the modified enzyme was completely inactive until irradiated with UV light, temporal regulation of polymerase activity was possible.}, number={32}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Chou, Chungjung and Young, Douglas D. and Deiters, Alexander}, year={2009}, pages={5950–5953} }
 @article{bereman_young_deiters_muddiman_2009, title={Development of a Robust and High Throughput Method for Profiling N-Linked Glycans Derived from Plasma Glycoproteins by NanoLC-FTICR Mass Spectrometry}, volume={8}, ISSN={["1535-3907"]}, DOI={10.1021/pr9002323}, abstractNote={Recent investigations continue to emphasize the importance of glycosylation in various diseases including cancer. In this work, we present a step-by-step protocol describing a method for N-linked glycan profiling of plasma glycoproteins by nanoflow liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS). A large experimental space was initially explored and is described herein. Three internal standards were spiked into the sample and provided normalization of plasma glycan abundance across different experimental conditions. Incubation methods and times and the effect of NP40 detergent on glycan abundance were explored. It was found that an 18-h incubation with no detergent led to the greatest ion abundance; however, data could be obtained in less than one day from raw plasma samples utilizing microwave irradiation or shorter incubation periods. The intersample precision of three different glycans was less than 5.5% (RSD) when the internal standards were added prior to the initial processing step. The high mass measurement accuracy (<3 ppm) afforded by the FTICR mass spectrometer provided confident identifications of several glycan species.}, number={7}, journal={JOURNAL OF PROTEOME RESEARCH}, author={Bereman, Michael S. and Young, Douglas D. and Deiters, Alexander and Muddiman, David C.}, year={2009}, month={Jul}, pages={3764–3770} }
 @article{edwards_young_deiters_2009, title={Light-Activated Cre Recombinase as a Tool for the Spatial and Temporal Control of Gene Function in Mammalian Cells}, volume={4}, ISSN={["1554-8937"]}, DOI={10.1021/cb900041s}, abstractNote={Cre recombinase catalyzes DNA exchange between two conserved lox recognition sites. The enzyme has extensive biological application, from basic cloning to engineering knock-out and knock-in organisms. Widespread use of Cre is due to its simplicity and effectiveness, but the enzyme and the recombination event remain difficult to control with high precision. To obtain such control we report the installation of a light-responsive o-nitrobenzyl caging group directly in the catalytic site of Cre, inhibiting its activity. Prior to irradiation, caged Cre is completely inactive, as demonstrated both in vitro and in mammalian cell culture. Exposure to non-damaging UVA light removes the caging group and restores recombinase activity. Tight spatio-temporal control over DNA recombination is thereby achieved.}, number={6}, journal={ACS CHEMICAL BIOLOGY}, author={Edwards, Wesleigh F. and Young, Douglas D. and Deiters, Alexander}, year={2009}, month={Jun}, pages={441–445} }
 @article{young_garner_yoder_deiters_2009, title={Light-activation of gene function in mammalian cells via ribozymes}, ISSN={1359-7345 1364-548X}, url={http://dx.doi.org/10.1039/b819375d}, DOI={10.1039/b819375d}, abstractNote={A ribozyme based gene control element enabled the spatio-temporal regulation of gene function in mammalian cell culture with light.}, number={5}, journal={Chem. Commun.}, publisher={Royal Society of Chemistry (RSC)}, author={Young, Douglas D. and Garner, R. Aaron and Yoder, Jeffrey A. and Deiters, Alexander}, year={2009}, pages={568–570} }
 @article{young_teske_deiters_2009, title={Open-Vessel Microwave-Mediated [2+2+2]-Cyclotrimerization Reactions}, ISSN={["1437-210X"]}, DOI={10.1055/s-0029-1218149}, abstractNote={[2+2+2]-Cyclotrimerization reactions often suffer from low reaction rates and low chemoselectivity. We are reporting a solution to both problems through the use of open-vessel conditions for microwave-mediated cyclotrimerization reactions.}, number={22}, journal={SYNTHESIS-STUTTGART}, author={Young, Douglas D. and Teske, Jesse A. and Deiters, Alexander}, year={2009}, month={Nov}, pages={3785–3790} }
 @article{young_govan_lively_deiters_2009, title={Photochemical Regulation of Restriction Endonuclease Activity}, volume={10}, ISSN={["1439-7633"]}, DOI={10.1002/cbic.200900090}, abstractNote={Abstract}, number={10}, journal={CHEMBIOCHEM}, author={Young, Douglas D. and Govan, Jeane M. and Lively, Mark O. and Deiters, Alexander}, year={2009}, month={Jul}, pages={1612–1616} }
 @article{young_lusic_lively_deiters_2009, title={Restriction enzyme-free mutagenesis via the light regulation of DNA polymerization}, volume={37}, number={8}, journal={Nucleic Acids Research}, author={Young, D. D. and Lusic, H. and Lively, M. O. and Deiters, A.}, year={2009} }
 @article{edwards_young_deiters_2009, title={The effect of microwave irradiation on DNA hybridization}, volume={7}, ISSN={["1477-0539"]}, DOI={10.1039/b903609a}, abstractNote={The effect of microwave irradiation on DNA/DNA hybridization has been studied under controlled power and temperature conditions. It was discovered that microwave irradiation led to the melting of double-stranded deoxyoligonucleotides well below their thermal melting temperature and independent of the length of the deoxyoligonucleotides. These observations indicate a specific interaction of microwaves with DNA, and have important implications in the chemical or enzymatic processing of DNA under microwave heating.}, number={12}, journal={ORGANIC & BIOMOLECULAR CHEMISTRY}, author={Edwards, Wesleigh F. and Young, Douglas D. and Deiters, Alexander}, year={2009}, pages={2506–2508} }
 @article{mciver_young_deiters_2008, title={A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine}, ISSN={["1359-7345"]}, DOI={10.1039/b811068a}, abstractNote={A convergent and flexible synthesis of substituted triphenylenes, azatriphenylenes, and the cytotoxic alkaloids dehydrotylophorine and tylophorine has been developed.}, number={39}, journal={CHEMICAL COMMUNICATIONS}, author={McIver, Andrew and Young, Douglas D. and Deiters, Alexander}, year={2008}, pages={4750–4752} }
 @article{young_lusic_lively_yoder_deiters_2008, title={Gene Silencing in Mammalian Cells with Light-Activated Antisense Agents}, volume={9}, ISSN={1439-4227 1439-7633}, url={http://dx.doi.org/10.1002/cbic.200800627}, DOI={10.1002/cbic.200800627}, abstractNote={Detailed knowledge of the external regulation of gene func-tion is a fundamental necessity in order to annotate sequencedgenomes and to understand biological processes in single cellsand multicellular organisms. One of the most widely used ap-proaches for the down-regulation of specific genes is the ap-plication of antisense agents. Antisense agents are oligomersthat have the ability to hybridize sequence specificslly tomRNAs, inhibiting translation and potentially leading to mRNAdegradation through RNAse H recruitment.}, number={18}, journal={ChemBioChem}, publisher={Wiley}, author={Young, Douglas D. and Lusic, Hrvoje and Lively, Mark O. and Yoder, Jeffrey A. and Deiters, Alexander}, year={2008}, month={Dec}, pages={2937–2940} }
 @article{young_deiters_2008, title={Light-regulated RNA-small molecule interactions}, volume={9}, ISSN={["1439-4227"]}, DOI={10.1002/cbic.200800051}, abstractNote={The development of light-regulated processes represents a noninvasive means to exert a high level of spatial and temporal control over a chemical or biological system.[1] The ability to light regulate the activity of biologically relevant molecules by the installation of photolabile protecting groups that are removed upon irradiation with ultraviolet light has been demonstrated numerous times in this context. Examples of this approach include the regulation of gene expression,[2] protein production,[3] protein function,[4] as well as antisense,[5] DNA,[6] and RNA function.[7] Other caged biologically relevant small molecules include ATP, Ca2+, theophylline, and fatty acids.[8] However, the decaging process only allows for the irreversible activation or deactivation of the system under study, thus limiting the scope of its utility.}, number={8}, journal={CHEMBIOCHEM}, author={Young, Douglas D. and Deiters, Alexander}, year={2008}, month={May}, pages={1225–1228} }
 @article{young_edwards_lusic_lively_deiters_2008, title={Light-triggered polymerase chain reaction}, ISSN={["1364-548X"]}, DOI={10.1039/b715152g}, abstractNote={Photochemical control of the polymerase chain reaction has been achieved through the incorporation of light-triggered nucleotides into DNA.}, number={4}, journal={CHEMICAL COMMUNICATIONS}, author={Young, Douglas D. and Edwards, Wesleigh F. and Lusic, Hrvoje and Lively, Mark O. and Deiters, Alexander}, year={2008}, pages={462–464} }
 @article{young_nichols_kelly_deiters_2008, title={Microwave activation of enzymatic catalysis}, volume={130}, ISSN={["0002-7863"]}, DOI={10.1021/ja802404g}, abstractNote={Microwave irradiation can be used to regulate biocatalysis. Herein, the utilization of hyperthermophilic enzymes in a microwave reactor is reported. While these enzymes are inactive at low temperatures, they can be activated with microwave irradiation. To the best of our knowledge, this is the first illustration of a specific microwave effect in enzymatic catalysis.}, number={31}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Young, Douglas D. and Nichols, Jason and Kelly, Robert M. and Deiters, Alexander}, year={2008}, month={Aug}, pages={10048-+} }
 @article{young_torres-kolbus_deiters_2008, title={Microwave-assisted synthesis of unnatural amino acids}, volume={18}, ISSN={["0960-894X"]}, DOI={10.1016/j.bmcl.2008.09.025}, abstractNote={Microwave irradiation has been proven to be a useful tool in the rapid assembly of racemic unnatural amino acids in only two steps. Additional benefits of this methodology are the commercial availability of the inexpensive starting materials and the high yields and high purities of the final amino acid products.}, number={20}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Young, Douglas D. and Torres-Kolbus, Jessica and Deiters, Alexander}, year={2008}, month={Oct}, pages={5478–5480} }
 @article{gumireddy_young_xiong_hogenesch_huang_deiters_2008, title={Small-molecule inhibitors of microRNA miR-21 function}, volume={47}, ISSN={["1521-3773"]}, DOI={10.1002/anie.200801555}, abstractNote={MicroRNAs (miRNAs) have recently emerged as an important class of gene regulators, and their misregulation has been linked to a variety of cancers. Small molecule inhibitors of miRNAs would be important tools to elucidate the detailed mechanisms of miRNA function and provide lead structures for the development of new therapeutics. We are reporting a cellular screen for miRNA pathway inhibitors and the first small molecule modifiers of miRNA function.}, number={39}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Gumireddy, Kiranmai and Young, Douglas D. and Xiong, Xin and Hogenesch, John B. and Huang, Qihong and Deiters, Alexander}, year={2008}, pages={7482–7484} }
 @article{zou_young_cruz-montanez_deiters_2008, title={Synthesis of Anthracene and Azaanthracene Fluorophores via [2+2+2] Cyclotrimerization Reactions}, volume={10}, ISSN={["1523-7052"]}, DOI={10.1021/ol8019549}, abstractNote={A highly convergent [2+2+2] cyclotrimerization approach to anthracenes and 2-azaanthracenes has been developed. It allows for the facile introduction of the anthracene moiety on alkyne and nitrile bearing molecules and the rapid construction of compound arrays. This is showcased in the assembly of a collection of fluorophores and their photochemical evaluation.}, number={20}, journal={ORGANIC LETTERS}, author={Zou, Yan and Young, Douglas D. and Cruz-Montanez, Alejandra and Deiters, Alexander}, year={2008}, month={Oct}, pages={4661–4664} }
 @article{young_deiters_2007, title={A general approach to chemo- and regioselective cyclotrimerization reactions}, volume={46}, ISSN={["1433-7851"]}, DOI={10.1002/anie.200700802}, abstractNote={Microwave-ready heterocycles: Cobalt-catalyzed [2+2+2] cyclotrimerization of nitrile derivatives with diynes anchored to a solid support under microwave irradiation provides a universal approach to pyridine, pyridone, and iminopyridine products. The reaction is completely chemo- and regioselective, and the products are obtained in excellent yield and high purity.}, number={27}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Young, Douglas D. and Deiters, Alexander}, year={2007}, pages={5187–5190} }
 @article{young_sripada_deiters_2007, title={Microwave-assisted solid-supported alkyne cyclotrimerization reactions for combinatorial chemistry}, volume={9}, ISSN={["1520-4766"]}, DOI={10.1021/cc070068b}, abstractNote={ADVERTISEMENT RETURN TO ISSUEReportNEXTMicrowave-Assisted Solid-Supported Alkyne Cyclotrimerization Reactions for Combinatorial ChemistryDouglas D. Young, Lakshminath Sripada, and Alexander DeitersView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 Cite this: J. Comb. Chem. 2007, 9, 5, 735–738Publication Date (Web):July 21, 2007Publication History Received4 May 2007Published online21 July 2007Published inissue 1 September 2007https://pubs.acs.org/doi/10.1021/cc070068bhttps://doi.org/10.1021/cc070068bbrief-reportACS PublicationsCopyright © 2007 American Chemical SocietyRequest reuse permissionsArticle Views754Altmetric-Citations35LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Aromatic compounds,Electromagnetic radiation,Hydrocarbons,Irradiation,Reactivity Get e-Alerts}, number={5}, journal={JOURNAL OF COMBINATORIAL CHEMISTRY}, author={Young, Douglas D. and Sripada, Lakshminath and Deiters, Alexander}, year={2007}, pages={735–738} }
 @article{lusic_young_lively_deiters_2007, title={Photochemical DNA activation}, volume={9}, ISSN={["1523-7052"]}, DOI={10.1021/ol070455u}, abstractNote={A new photocaged nucleoside was synthesized and incorporated into DNA with the use of standard synthesis conditions. This approach enabled the disruption of specific H-bonds and allowed for the analysis of their contribution to the activity of a DNAzyme. Brief irradiation with nonphotodamaging UV light led to rapid decaging and almost quantitative restoration of DNAzyme activity. The developed strategy has the potential to find widespread application in the light-induced regulation of oligonucleotide function.}, number={10}, journal={ORGANIC LETTERS}, author={Lusic, Hrvoje and Young, Douglas D. and Lively, Mark O. and Deiters, Alexander}, year={2007}, month={May}, pages={1903–1906} }
 @article{young_deiters_2007, title={Photochemical activation of protein expression in bacterial cells}, volume={46}, ISSN={["1521-3773"]}, DOI={10.1002/anie.200700057}, abstractNote={Small-molecule-inducible gene-expression systems are available in a variety of cell types including bacterial cells, yeast cells, and mammalian cells. They have been used for conditional protein expression in higher organisms ranging from plants to mice. These systems are typically composed of a natural receptor taken from one organism and transferred into a second organism, in conjunction with a natural or unnatural small-molecule ligand that is orthogonal to all endogenous molecules of the organism of interest. Exposure of the organism to the small molecule typically activates gene expression, a process that has found application in the production of recombinant proteins, the programing of biological processes, and the study of gene function. Although this technique enables temporal control over gene function on a minute-to-hour timescale, it does not permit spatial control. A highly efficient way to simultaneously achieve spatial and temporal control over biological processes is the application of photocaging. The term “caging” defines the installation of a photoremovable group on a biologically active molecule, thus rendering the molecule inactive. Caging groups have been installed on small molecules, oligonucleotides, peptides, and proteins. Irradiation with UV light removes the caging group and restores biological activity. Recently, this approach has been applied to the light activation of small-molecule inducers of protein expression. Both reported systems, that is, the doxycycline and the nuclear hormone (for example, estradiol) conditional-geneexpression systems, are restricted to eukaryotic cells. Here we report a light-inducible gene-expression system which can be used in bacterial cells, plants, and mammalian organisms. It is based on the lactose (lac) repressor which binds to the lac operator (lacO), thereby inhibiting RNA polymerase from performing gene transcription. In presence of the small-molecule effector isopropyl-b-d-thio-galactoside (IPTG), the repressor is released from the DNA through an allosteric binding event, which results in a conformational change and leads to gene expression (Figure 1). The crystal structure of the LacI/IPTG complex (Protein Data Bank file no. 1LBH) reveals interactions between the small molecule and the protein in a tight binding pocket, as well as four essential hydrogen bonds between the 4-OH group and Arg197, the 3-OH group and Arg197, and also the 2-OH group and Asp274 and Asn246 (see the Supporting Information). We speculated that disruption of the hydrogen-bond network through the installation of a sterically demanding caging group on IPTG would inhibit the formation of the LacI/IPTG complex and thereby inhibit gene expression. If the installed group is removable through irradiation with UV light, IPTG can be generated in a spatiotemporal manner, thereby enabling spatiotemporal control over protein expression. In order to achieve this, the caged IPTG 1 was synthesized in a single step (78% yield) by the reaction of IPTG with 6-nitropiperonal (see the Experimental Section), which furnished selective dioxolan formation at the 4and 6-hydroxy groups. This is in accordance with the results of NMR experiments and previous observations in similar reactions. The caged IPTG 1 is nontoxic to bacterial cells and no degradation was observed under physiological conditions. Irradiation of an aqueous solution of 1 ( 0.5 mm, e365= 4533 cm m ) with nonphotodamaging UV light (handheld UV lamp, 365 nm, 0.5 Wcm ) for 5 min leads to quantitative formation of the ester 2, as a 1:1 mixture of regioisomers (4-OH/6-OH, Scheme 1 shows the 4-OH ester). The half life for the conversion 1!2 after irradiation depends on the concentration of 1 and amounts to 11 s at a concentration of 0.1 mm, 5.1 min at 0.5 mm, or 11.8 min at 1.0 mm (see the Supporting Information). This facile photolytic conversion of a 1,3-dioxane is in remarkable contrast to previous observations with bromohydroxycoumarin caged diols. The quantum yield (f= 0.131) for the photochemical conversion of 1 into 2 has been determined by 3,4-dimethoxynitrobenzene actinometry. The ester 2 is stable in an aqueous solution; however, as observed for other carbohydrate esters, 2 is hydrolyzed to IPTG by the esterases found in a cellular environment (t1/2= 63 min 2 min, see the Supporting Information). The growth of bacterial cells exposed to 0.5 mm concentrations of 1 and 2 revealed that the compounds do not reduce growth rates, are nontoxic, and are easily taken up by the cells (see the Supporting Information). Figure 1. IPTG-induced expression of an open reading frame (ORF) through formation of the IPTG/lac repressor complex.}, number={23}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Young, Douglas D. and Deiters, Alexander}, year={2007}, pages={4290–4292} }
 @article{young_deiters_2007, title={Photochemical control of biological processes}, volume={5}, ISSN={["1477-0539"]}, DOI={10.1039/b616410m}, abstractNote={Photochemical regulation of biological processes offers a high level of control to study intracellular mechanisms with unprecedented spatial and temporal resolution. This report summarizes the advances made in recent years, focusing predominantly on the in vivo regulation of gene function using irradiation with UV light. The majority of the described applications entail the utilization of photocaging groups installed either on a small molecule modulator of biomolecular function or directly on a biological macromolecule itself.}, number={7}, journal={ORGANIC & BIOMOLECULAR CHEMISTRY}, author={Young, Douglas D. and Deiters, Alexander}, year={2007}, pages={999–1005} }
 @article{senaiar_teske_young_deiters_2007, title={Synthesis of indanones via solid-supported [2+2+2] cyclotrimerization}, volume={72}, ISSN={["0022-3263"]}, DOI={10.1021/jo7013565}, abstractNote={A new facile approach toward natural and unnatural indanones has been developed, featuring a solid-supported [2+2+2] cyclotrimerization as the key step. This strategy has been applied to the chemo- and regioselective assembly of indanone arrays and to the total synthesis of a recently isolated indanone marine natural product.}, number={20}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Senaiar, Ramesh S. and Teske, Jesse A. and Young, Douglas D. and Deiters, Alexander}, year={2007}, month={Sep}, pages={7801–7804} }
 @article{young_deiters_2006, title={Photochemical hammerhead ribozyme activation}, volume={16}, ISSN={["1464-3405"]}, DOI={10.1016/j.bmcl.2006.02.034}, abstractNote={We report the light-activation of allosteric cis and trans acting ribozymes via decaging of a small organic molecule ligand. To achieve this effectively, we introduce an optimized N-caging group based on a nitrobenzyl core structure. This approach can potentially be employed toward a light-induced control of gene function.}, number={10}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Young, DD and Deiters, A}, year={2006}, month={May}, pages={2658–2661} }
 @article{senaiar_young_deiters_2006, title={Pyridines via solid-supported [2+2+2] cyclotrimerization}, DOI={10.1039/b515901f}, abstractNote={The formation of pyridines via a crossed [2 + 2 + 2] cycloaddition has been achieved on a solid-support for the first time.}, number={12}, journal={Chemical Communications (Cambridge, England)}, author={Senaiar, R. S. and Young, D. D. and Deiters, A.}, year={2006}, pages={1313–1315} }
 @article{young_senaiar_deiters_2006, title={Solid-supported [2+2+2] cyclotrimerizations}, volume={12}, ISSN={["0947-6539"]}, DOI={10.1002/chem.200501360}, abstractNote={Abstract}, number={21}, journal={CHEMISTRY-A EUROPEAN JOURNAL}, author={Young, Douglas D. and Senaiar, Ramesh S. and Deiters, Alexander}, year={2006}, month={Jul}, pages={5563–5568} }