Research Topics
Genomes and GenesSpecies | Alexander DeitersSummaryAffiliation: North Carolina State University Country: USA Publications
Research Grants
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Publications
Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesisAlexander Deiters
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA
Chem Rev 104:2199-238. 2004
Photocaged morpholino oligomers for the light-regulation of gene function in zebrafish and Xenopus embryosAlexander Deiters
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, United States
J Am Chem Soc 132:15644-50. 2010..Our results suggest that photocaged morpholinos are readily synthesized and highly efficacious tools for light-activated spatiotemporal control of gene expression in multiple contexts...
Small molecule modifiers of the microRNA and RNA interference pathwayAlexander Deiters
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695 8204, USA
AAPS J 12:51-60. 2010..Thus, the activation of tumor-suppressive miRNAs and the inhibition of oncogenic miRNAs by small molecules have the potential to provide a fundamentally new approach for the development of cancer therapeutics...
Light activation as a method of regulating and studying gene expressionAlexander Deiters
North Carolina State University, Department of Chemistry, Raleigh, NC 27695 8204, USA
Curr Opin Chem Biol 13:678-86. 2009..UV light irradiation then removes the caging group and activates the molecule, enabling control over gene activity with high spatial and temporal resolution...
Activation and deactivation of DNAzyme and antisense function with light for the photochemical regulation of gene expression in mammalian cellsDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Am Chem Soc 132:6183-93. 2010..This represents the first example of gene silencing antisense agents that can be turned on and turned off in mammalian tissue culture...
A photoactivatable small-molecule inhibitor for light-controlled spatiotemporal regulation of Rho kinase in live embryosAllison R Morckel
Department of Molecular Biomedical Sciences, College of Veterinary Medicine, North Carolina State University, Raleigh, NC 27606, USA
Development 139:437-42. 2012....
The human mitochondrial tRNAMet: structure/function relationship of a unique modification in the decoding of unconventional codonsYann Bilbille
Department of Molecular and Structural Biochemistry, North Carolina State University, Raleigh, NC 27695, USA
J Mol Biol 406:257-74. 2011....
Light-activated deoxyguanosine: photochemical regulation of peroxidase activityHrvoje Lusic
North Carolina State University, Department of Chemistry, Raleigh, NC 27695, USA
Mol Biosyst 4:508-11. 2008..Photochemical activation of a deoxyribozyme with peroxidase activity was achieved by the synthesis and incorporation of a caged deoxyguanosine...
Generating permissive site-specific unnatural aminoacyl-tRNA synthetasesShigeki J Miyake-Stoner
Department of Chemistry, Franklin and Marshall College, Lancaster, Pennsylvania 17604 3003, USA
Biochemistry 49:1667-77. 2010..We expect that results of this work will increase the accessibility of UAA technology and the use of new UAAs in proteins...
Stabilization and photochemical regulation of antisense agents through PEGylationJeane M Govan
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, United States
Bioconjug Chem 22:2136-42. 2011..By using a photocleavable PEG group (PhotoPEG), antisense activity can be regulated with high spatial and temporal resolution, paving the way for precise regulation of gene expression in biological systems...
Restriction enzyme-free mutagenesis via the light regulation of DNA polymerizationDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, NC 27607 8204, USA
Nucleic Acids Res 37:e58. 2009..Additionally, this approach enables not only site-directed mutations, but also the insertion of DNA strands of any length into plasmids and the deletion of entire genes from plasmids...
Microwave-assisted synthesis of unnatural amino acidsDouglas D Young
Department of Chemistry, North Carolina State University, Campus Box 8204, Raleigh, NC 27695 8204, USA
Bioorg Med Chem Lett 18:5478-80. 2008..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...
Photochemical regulation of restriction endonuclease activityDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Chembiochem 10:1612-6. 2009..Interestingly, these groups do not appear to dramatically affect initial binding of the enzyme to the DNA substrate, but rather prevent recognition of the specific cleavage site...
Light-regulated RNA-small molecule interactionsDouglas D Young
North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA
Chembiochem 9:1225-8. 2008
Phenanthridine synthesis via [2+2+2] cyclotrimerization reactionsLakshminath Sripada
Department of Chemistry, North Carolina State University, Raleigh, NC 27695 8204, USA
Org Biomol Chem 6:263-5. 2008..A concise synthesis of phenanthridines via a microwave-assisted [2+2+2] cyclotrimerization reaction has been developed...
Photochemical control of bacterial signal processing using a light-activated erythromycinLaura Gardner
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Mol Biosyst 7:2554-7. 2011..coli. We applied this photochemical gene switch to the construction of a light-triggered logic gate, a light-controlled band-pass filter, as well as spatial and temporal control of gene expression...
High-throughput luciferase reporter assay for small-molecule inhibitors of microRNA functionColleen M Connelly
North Carolina State University, Raleigh, NC, USA
J Biomol Screen 17:822-8. 2012..The described reporter assay will enable the high-throughput screening of small-molecule miR-122 inhibitors and can be readily extended to other miRNAs...
Heterotaxin: a TGF-β signaling inhibitor identified in a multi-phenotype profiling screen in Xenopus embryosMichael K Dush
Department of Molecular Biomedical Sciences, College of Veterinary Medicine, North Carolina State University, 4700 Hillsborough Street, Raleigh, NC 27606, USA
Chem Biol 18:252-63. 2011..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...
Photochemical control of biological processesDouglas D Young
North Carolina State University, Department of Chemistry, Campus Box 8204, Raleigh, NC 27695, USA
Org Biomol Chem 5:999-1005. 2007..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...
Photocleavable polyethylene glycol for the light-regulation of protein functionWesleigh E Georgianna
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Bioconjug Chem 21:1404-7. 2010..Herein, we report the synthesis of a photocleavable PEG reagent (PhotoPEG) and its application to the light-regulation of enzyme activity...
Photochemical activation of protein expression in bacterial cellsDouglas D Young
North Carolina State University, Department of Chemistry, Campus Box 8204, Raleigh, NC 27695-8204, USA
Angew Chem Int Ed Engl 46:4290-2. 2007
Tricyclic alkaloid core structures assembled by a cyclotrimerization-coupled intramolecular nucleophilic substitution reactionAndrew L McIver
North Carolina State University, Department of Chemistry, Raleigh, North Carolina 27695 8204, USA
Org Lett 12:1288-91. 2010..This methodology enabled the facile assembly of the spiroindolinone framework of citrinadins A and B, and cyclopiamine B...
Regulation of transcription through light-activation and light-deactivation of triplex-forming oligonucleotides in mammalian cellsJeane M Govan
Department of Chemistry, North Carolina State University, Raleigh, 27695, United States
ACS Chem Biol 7:1247-56. 2012..In addition, hairpin loop structures were found to significantly increase the efficacy of phosphodiester DNA-based TFOs in tissue culture...
Photochemical control of DNA decoy function enables precise regulation of nuclear factor κB activityJeane M Govan
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Am Chem Soc 133:13176-82. 2011..This is the first example of a caged DNA decoy for the photochemical regulation of gene expression in mammalian cells and represents an important addition to the toolbox of light-controlled gene regulatory agents...
Photocaged t7 RNA polymerase for the light activation of transcription and gene function in pro- and eukaryotic cellsChungjung Chou
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Chembiochem 11:972-7. 2010..The ability to achieve spatiotemporal regulation of orthogonal RNA synthesis enables the precise dissection and manipulation of a wide range of cellular events, including gene function...
Microwave activation of enzymatic catalysisDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Am Chem Soc 130:10048-9. 2008..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...
Photochemical DNA activationHrvoje Lusic
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Org Lett 9:1903-6. 2007..The developed strategy has the potential to find widespread application in the light-induced regulation of oligonucleotide function...
Synthesis of anthracene and azaanthracene fluorophores via [2+2+2] cyclotrimerization reactionsYan Zou
Department of Chemistry, North Carolina State University, Campus Box 8204, Raleigh, North Carolina 27695 8204, USA
Org Lett 10:4661-4. 2008..This is showcased in the assembly of a collection of fluorophores and their photochemical evaluation...
Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramiditeHrvoje Lusic
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
Org Lett 12:916-9. 2010..Furthermore, its installation on a thymidine phosphoramidite is described. This caging group is efficiently removed through light-irradiation at 365 nm...
Spatiotemporal control of microRNA function using light-activated antagomirsColleen M Connelly
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA
Mol Biosyst 8:2987-93. 2012..The presented approach enables the precise regulation of miRNA function and miRNA networks with unprecedented spatial and temporal resolution using UV irradiation and can be extended to any miRNA of interest...
Microwave-mediated nickel-catalyzed cyclotrimerization reactions: total synthesis of illudinineJesse A Teske
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695 8204, USA
J Org Chem 73:342-5. 2008..This represents the first example of a Ni-catalyzed cyclotrimerization reaction in total synthesis...
Recent advances in the photochemical control of protein functionChad W Riggsbee
Department of Chemistry, North Carolina State University, Raleigh, NC 27607, USA
Trends Biotechnol 28:468-75. 2010..In addition, examples of the photochemical control of protein function through the application of genetically engineered natural-light receptors are presented...
A genetically encoded fluorescent amino acidDaniel Summerer
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, SR202, La Jolla, CA 92037, USA
Proc Natl Acad Sci U S A 103:9785-9. 2006..The strategy described here should be applicable to a number of different fluorophores in both prokaryotic and eukaryotic organisms, and it should facilitate both biochemical and cellular studies of protein structure and function...
A genetically encoded photocaged tyrosineAlexander Deiters
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA
Angew Chem Int Ed Engl 45:2728-31. 2006
Total synthesis of cryptoacetalideYan Zou
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Org Chem 75:5355-8. 2010..Key steps of the synthesis are a microwave-mediated [2+2+2] cyclo-trimerization reaction to construct the central benzene ring, and a light-mediated radical cyclization to assemble the spiro-ketal moiety...
Microwave-assisted solid-supported alkyne cyclotrimerization reactions for combinatorial chemistryDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA
J Comb Chem 9:735-8. 2007
Synthesis of the pyridine core of cyclothiazomycinYan Zou
North Carolina State University, Department of Chemistry, Raleigh, North Carolina 27695 8204, USA
Org Lett 13:4352-5. 2011....
A cyclotrimerization route to cannabinoidsJesse A Teske
North Carolina State University, Department of Chemistry, Raleigh, North Carolina 27695 8204, USA
Org Lett 10:2195-8. 2008..This approach provides a high level of synthetic flexibility allowing for the facile synthesis of cannabinoid analogues...
Synthesis and investigation of the 5-formylcytidine modified, anticodon stem and loop of the human mitochondrial tRNAMetHrvoje Lusic
Department of Chemistry, Department of Molecular and Structural Biochemistry, North Carolina State University, Raleigh, NC 27695 and Dharmacon, 2650 Crescent Drive 100, Lafayette, CO 80026, USA
Nucleic Acids Res 36:6548-57. 2008..The modification contributes to the tRNA's anticodon domain structure, thermodynamic properties and its ability to bind codons AUA and AUG in translational initiation and elongation...
Light-controlled synthetic gene circuitsLaura Gardner
North Carolina State University, Department of Chemistry, Raleigh, NC 27695, United States
Curr Opin Chem Biol 16:292-9. 2012..Herein we describe recent advancements in the area of light-controlled synthetic networks...
Small molecule modifiers of microRNA miR-122 function for the treatment of hepatitis C virus infection and hepatocellular carcinomaDouglas D Young
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Am Chem Soc 132:7976-81. 2010..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...
DNA computation: a photochemically controlled AND gateAlex Prokup
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695 8204, USA
J Am Chem Soc 134:3810-5. 2012..This connection is important for the further development of an interface between DNA logic gates and electronic devices, enabling the connection of biological systems with electrical circuits...
Light regulation of protein dimerization and kinase activity in living cells using photocaged rapamycin and engineered FKBPAndrei V Karginov
Department of Pharmacology, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States
J Am Chem Soc 133:420-3. 2011..Modification of this approach enabled light-triggered activation of a protein kinase and initiation of kinase-induced phenotypic changes in vivo...
Hydrogen peroxide induced activation of gene expression in mammalian cells using boronate estrone derivativesJeane M Govan
Department of Chemistry, North Carolina State University, Raleigh, NC 27695 8204, USA
Angew Chem Int Ed Engl 51:9066-70. 2012..This sensor is highly sensitive and specific for H(2)O(2)...
The effect of microwave irradiation on DNA hybridizationWesleigh F Edwards
Department of Chemistry, North Carolina State University, Raleigh, NC 27695 8204, USA
Org Biomol Chem 7:2506-8. 2009..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...
Development of a robust and high throughput method for profiling N-linked glycans derived from plasma glycoproteins by NanoLC-FTICR mass spectrometryMichael S Bereman
W M Keck FT ICR Mass Spectrometry Laboratory, Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, USA
J Proteome Res 8:3764-70. 2009..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...
In vivo incorporation of an alkyne into proteins in Escherichia coliAlexander Deiters
Department of Chemistry, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
Bioorg Med Chem Lett 15:1521-4. 2005..These evolved tRNA-synthetase pairs were used to site-specifically incorporate an alkynyl group into a protein, which was subsequently conjugated with fluorescent dyes by a [3+2]-cycloaddition reaction under mild reaction conditions...
Photochemical hammerhead ribozyme activationDouglas D Young
North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA
Bioorg Med Chem Lett 16:2658-61. 2006..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...
Site-specific in vivo labeling of proteins for NMR studiesAlexander Deiters
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA
Chembiochem 6:55-8. 2005
General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloidsAlexander Deiters
Department of Chemistry and Biochemistry, University of Texas, Austin, Texas 78712, USA
J Org Chem 71:6547-61. 2006..The ABD --> ABCD approach to these alkaloids featured a novel one-pot sequence of an RCM reaction and a zirconocene-catalyzed carbomagnesation followed by a second RCM to generate the D-ring...
Small-molecule inhibitors of microrna miR-21 functionKiranmai Gumireddy
The Wistar Institute, 3601 Spruce Street, Philadelphia, PA 19104, USA
Angew Chem Int Ed Engl 47:7482-4. 2008
Stereoselective total synthesis of dihydrocorynantheolAlexander Deiters
Department of Chemistry and Biochemistry, The University of Texas, Austin 78712, USA
Org Lett 4:3243-5. 2002..Since no protecting groups were used, the present synthesis of 1 is exceedingly concise, consisting of only eight distinct operations...
Research Grants
- Switchable Systems for Spatio-Temporal Control of Gene Expression in ZebrafishAlexander Deiters; Fiscal Year: 2007..aptamers, expression plasmids, etc.) and protocols (e.g. for organic synthesis, UV irradiation, etc.) will be made accessible to the scientific community via a dedicated web-page. ..
- Switchable Systems for Spatio-Temporal Control of Gene Expression in ZebrafishAlexander Deiters; Fiscal Year: 2009..aptamers, expression plasmids, etc.) and protocols (e.g. for organic synthesis, UV irradiation, etc.) will be made accessible to the scientific community via a dedicated web-page. ..
- Switchable Systems for Spatio-Temporal Control of Gene Expression in ZebrafishAlexander Deiters; Fiscal Year: 2010..aptamers, expression plasmids, etc.) and protocols (e.g. for organic synthesis, UV irradiation, etc.) will be made accessible to the scientific community via a dedicated web-page. ..
- Switchable Systems for Spatio-Temporal Control of Gene Expression in ZebrafishAlexander Deiters; Fiscal Year: 2010..aptamers, expression plasmids, etc.) and protocols (e.g. for organic synthesis, UV irradiation, etc.) will be made accessible to the scientific community via a dedicated web-page. ..
