“…Through the convergent Sonogashira coupling of an iodo-nucleobase to an acetylenic linker, dimers and tetramers of A and U fused bases were generated to explore these chain molecules (Figure 126). [709][710][711][712] UV studies on these single strands did not show any evidence of base interactions, indicating that intrastrand base stacking had been disrupted through this backbone modification. In a related system, phosphodiesterfused A and U bases were single-site incorporated into 14-mer DNA strands and led to duplex formation destabilized by an amount on the order of only one mismatch pair.…”
Section: Fused Sugar−base Backbonesmentioning
confidence: 93%
“… 123 Representative examples of PNA structural modifications. 124 Crystal structure of a peptide nucleic acid duplex (left) . For clarity, one strand is colored yellow and the other uses conventional atom colors: PNA 2 −DNA triplex (right) . Four chains are shown.…”
Section: Pnasmentioning
confidence: 99%
“…A recent series of investigations was undertaken to determine if a fusion between the sugar and the nucleobase would provide conformational accessibility to intermolecular complexation. Through the convergent Sonogashira coupling of an iodo-nucleobase to an acetylenic linker, dimers and tetramers of A and U fused bases were generated to explore these chain molecules (Figure ). − UV studies on these single strands did not show any evidence of base interactions, indicating that intrastrand base stacking had been disrupted through this backbone modification. In a related system, phosphodiester-fused A and U bases were single-site incorporated into 14-mer DNA strands and led to duplex formation destabilized by an amount on the order of only one mismatch pair. , These examples clearly demonstrate that the double-helix architecture has a strong preference for comblike structures where the backbone adopts conformations that project nucleobases in orthogonal orientations to the helical axis.…”
He attended Point Loma Nazarene University in San Diego, CA, where he worked with Professor Victor L. Heasley on the halogenation of unsaturated carbonyl compounds. After receiving his B.A. degree in Chemistry in 1997, he began his graduate career at the University of Illinois with Professor Jeffrey S. Moore. Currently he is in his fifth year investigating solvent effects on the helix−coil transition in oligo(m-phenylene ethynylene) foldamers. Matthew J. Mio (left) was born in Michigan in 1974. He attended the University of Detroit Mercy, where he worked with Professor Kevin. D. Belfield (now at the University of Central Florida) on the synthesis of nonlinear optical chromophores for use in polymeric systems. He graduated with his B.S. degree in Chemistry in 1997. Later that year, he began his graduate career at the University of Illinois at Urbana−Champaign with Professor Jeffrey S. Moore. There, Matt studied the synthesis and solution/ solid-state properties of oligo(m-phenylene ethynylene) foldamers and graduated with his Ph.D. degree in 2001. He then went to the Chemistry Department at Macalester College (St. Paul, MN) as a Mellon Postdoctoral Fellow to study the synthesis of novel CpCo−cyclobutadienyl-bridged cyclophanes with Professor Ronald G. Brisbois. Thomas S. Hughes (right) is currently a postdoctoral fellow in the research group of Professor Jeff Moore at the University of Illinois. He was born in 1970 in Philadelphia, PA, and received his B.S. degree from Temple University in 1991. In 1999 he received his Ph.D. degree from Cornell University, where he worked in the laboratories of Professor Barry Carpenter. He is currently studying the association kinetics of the binding of a helical oligomer to a rodlike guest. He is also investigating the thermodynamics of oligo(phenylene ethynylene) folding using molecular mechanics. Jeffrey S. Moore (second from right) was born in Illinois in 1962. After receiving his B.S. degree in Chemistry from the University of Illinois in 1984, he completed his Ph.D. degree in Materials Science and Engineering, also at the University of Illinois, with Samuel Stupp (1989). He then went to the California Institute of Technology as an NSF postdoctoral fellow to study with Robert Grubbs. In 1990 he joined the chemistry faculty at the University of Michigan in Ann Arbor. He returned to the University of Illinois in 1993, where he is currently a Professor of Chemistry and Materials Science and Engineering. In 1995 he became a part-time faculty member of the Beckman Institute for Advanced Science and Technology, where he now serves as co-chairman of the Molecular and Electronic Nanostructures Main Research Theme. Ryan B. Prince was born in Robbinsdale, MN, in 1972. He graduated from Southeast Missouri State University in 1995 with his B.S. degree in Chemistry, where he worked for Professor Jin K. Gong on the synthesis and characterization of transition-metal complexes that bind and activate carbon dioxide. He then went to the University of Illinois and worked with Professor Jeffrey...
“…Through the convergent Sonogashira coupling of an iodo-nucleobase to an acetylenic linker, dimers and tetramers of A and U fused bases were generated to explore these chain molecules (Figure 126). [709][710][711][712] UV studies on these single strands did not show any evidence of base interactions, indicating that intrastrand base stacking had been disrupted through this backbone modification. In a related system, phosphodiesterfused A and U bases were single-site incorporated into 14-mer DNA strands and led to duplex formation destabilized by an amount on the order of only one mismatch pair.…”
Section: Fused Sugar−base Backbonesmentioning
confidence: 93%
“… 123 Representative examples of PNA structural modifications. 124 Crystal structure of a peptide nucleic acid duplex (left) . For clarity, one strand is colored yellow and the other uses conventional atom colors: PNA 2 −DNA triplex (right) . Four chains are shown.…”
Section: Pnasmentioning
confidence: 99%
“…A recent series of investigations was undertaken to determine if a fusion between the sugar and the nucleobase would provide conformational accessibility to intermolecular complexation. Through the convergent Sonogashira coupling of an iodo-nucleobase to an acetylenic linker, dimers and tetramers of A and U fused bases were generated to explore these chain molecules (Figure ). − UV studies on these single strands did not show any evidence of base interactions, indicating that intrastrand base stacking had been disrupted through this backbone modification. In a related system, phosphodiester-fused A and U bases were single-site incorporated into 14-mer DNA strands and led to duplex formation destabilized by an amount on the order of only one mismatch pair. , These examples clearly demonstrate that the double-helix architecture has a strong preference for comblike structures where the backbone adopts conformations that project nucleobases in orthogonal orientations to the helical axis.…”
He attended Point Loma Nazarene University in San Diego, CA, where he worked with Professor Victor L. Heasley on the halogenation of unsaturated carbonyl compounds. After receiving his B.A. degree in Chemistry in 1997, he began his graduate career at the University of Illinois with Professor Jeffrey S. Moore. Currently he is in his fifth year investigating solvent effects on the helix−coil transition in oligo(m-phenylene ethynylene) foldamers. Matthew J. Mio (left) was born in Michigan in 1974. He attended the University of Detroit Mercy, where he worked with Professor Kevin. D. Belfield (now at the University of Central Florida) on the synthesis of nonlinear optical chromophores for use in polymeric systems. He graduated with his B.S. degree in Chemistry in 1997. Later that year, he began his graduate career at the University of Illinois at Urbana−Champaign with Professor Jeffrey S. Moore. There, Matt studied the synthesis and solution/ solid-state properties of oligo(m-phenylene ethynylene) foldamers and graduated with his Ph.D. degree in 2001. He then went to the Chemistry Department at Macalester College (St. Paul, MN) as a Mellon Postdoctoral Fellow to study the synthesis of novel CpCo−cyclobutadienyl-bridged cyclophanes with Professor Ronald G. Brisbois. Thomas S. Hughes (right) is currently a postdoctoral fellow in the research group of Professor Jeff Moore at the University of Illinois. He was born in 1970 in Philadelphia, PA, and received his B.S. degree from Temple University in 1991. In 1999 he received his Ph.D. degree from Cornell University, where he worked in the laboratories of Professor Barry Carpenter. He is currently studying the association kinetics of the binding of a helical oligomer to a rodlike guest. He is also investigating the thermodynamics of oligo(phenylene ethynylene) folding using molecular mechanics. Jeffrey S. Moore (second from right) was born in Illinois in 1962. After receiving his B.S. degree in Chemistry from the University of Illinois in 1984, he completed his Ph.D. degree in Materials Science and Engineering, also at the University of Illinois, with Samuel Stupp (1989). He then went to the California Institute of Technology as an NSF postdoctoral fellow to study with Robert Grubbs. In 1990 he joined the chemistry faculty at the University of Michigan in Ann Arbor. He returned to the University of Illinois in 1993, where he is currently a Professor of Chemistry and Materials Science and Engineering. In 1995 he became a part-time faculty member of the Beckman Institute for Advanced Science and Technology, where he now serves as co-chairman of the Molecular and Electronic Nanostructures Main Research Theme. Ryan B. Prince was born in Robbinsdale, MN, in 1972. He graduated from Southeast Missouri State University in 1995 with his B.S. degree in Chemistry, where he worked for Professor Jin K. Gong on the synthesis and characterization of transition-metal complexes that bind and activate carbon dioxide. He then went to the University of Illinois and worked with Professor Jeffrey...
“…100 However, aryl azides have also been found to be relatively unreactive in click reactions and usually require extensive heating for a reaction to occur. [101][102][103] The Hudson group demonstrated the unreactivity of 8 …”
This dissertation, written by Jessica Zayas, and entitled Strain Promoted Click Chemistry of 8-Azidopurine and 5-Azidopyrimidine Nucleosides and Nucleotides with Cyclooctynes and Applications to Living Cell Imaging, having been approved in respect to style and intellectual content, is referred to you for judgment.We have read this dissertation and recommend that it be approved. The SPAAC methodology developed has also been applied to study the cellular targets in protozoal parasite, Trichomonas vaginalis and bacteria, Pseudomonas aeruginosa. The 9-(2-deoxy-2-fluoro-β,D-arabino-furanosyl)adenine (arabino-F-Ado) was modified with an azido moiety at the C8 position for use in click chemistry. Tagging and subcellular localization studies using azido modified arabino-F-Ado could provide insight into the mechanism of action of arabino-F-Ado.
_______________________________________
“…These compounds may form stable complexes with uridine oligonucleotides and their 6,5‘-acetyleno-linked analogues. The synthesis of dimers 396 was achieved by a Sonogashira reaction in which cross-coupling of a C-8-halogenated monomer 394 with a C-5‘-ethynylated nucleoside 395 occurs . The optimized catalytic system consists of Pd 2 (dba) 3 , Et 3 N, and 6 mol % of tris(furan-2-yl)phosphine, which accelerates the cross-coupling about 3-fold.…”
Section: K Precursors Of Oligonucleotides With a
Nucleobase-including...mentioning
A. Palladium Compounds and ComplexesOrganic synthesis generally makes use of palladium compounds in either the Pd(0) or Pd(II) oxidation state. Palladium(II) salts may be used either as stoichiometric reagents or as catalysts, while palladium(0) complexes are used only as catalysts.
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