935-13-7Relevant articles and documents
Furan-PNA: A mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA
Manicardi,Gyssels,Corradini,Madder
, p. 6930 - 6933 (2016)
We here report on the design and synthesis of tailor-made furan-modified peptide nucleic acid (PNA) probes for covalent targeting of single stranded DNA through a crosslinking strategy. After introducing furan-containing building blocks into a PNA sequence, hybridization and furan-oxidation based crosslinking to DNA is investigated. The structure of the crosslinked products is characterized and preliminary investigations concerning the application of these systems to double stranded DNA are shown.
Reversible Covalent Assembly of Nanoparticles through On-Surface Diels-Alder Reaction
Schütz, Markus B.,Lê, Khan,Ilyas, Shaista,Mathur, Sanjay
, p. 1552 - 1558 (2020/03/05)
We demonstrate here a controlled assembly of individual nanoscale building blocks into defined architectures based on chemospecific covalent bonding interactions. For this purpose, α-Fe2O3, γ-Fe2O3, and SiO2 nanoparticles decorated with surface-conjugated organic ligands were used for performing on-surface Diels-Alder reactions. Driven through their chemical affinity and surface-grafted complementary functionalities, nanoparticles underwent click-reactions to produce covalently organized nanostructures. An advantage of using the Diels-Alder reaction is its reversible nature, which was used to click and unclick the nanoparticles on demand. The efficiency and chemical specificity of this approach opens up another synthetic access to unify materials with complementary properties, where the thermoresponsive nature of particle assemblies imparts to them a fully reversible character. The covalent conjugation strategies demonstrated in this work potentially allow the use of a diverse range of particles and ligands for their applications in different disciplines such as medicine, optics, or photonics. The nanoparticles morphology and crystalline nature were investigated by TEM and XRD analysis, while the presence of surface attached groups was verified by NMR, FTIR, UV-vis, and ζ potential measurements.
Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion
Kim, Sun Min,Shin, Hun Yi,Kim, Dong Wan,Yang, Jung Woon
, p. 241 - 245 (2016/02/27)
A transition metal-free, chemoselective reaction was performed using the sodium tert-butoxide-oxygen (NaOtBu-O2) system, resulting in either oxidative dehomologation or direct oxidation of alcohols. In particular, the newly developed protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. The rational mechanism of this transformation was also demonstrated by performing an 18O isotopic labelling experiment. This protocol presents a straightforward method for biomass conversion of a lignin model compound to phenol and benzoic acid.
A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
supporting information, p. 7785 - 7788 (2014/08/05)
Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
Raney nickel-catalyzed hydrogenation of unsaturated carboxylic acids with sodium borohydride in water
Rao, Gopal Krishna,Gowda, Narendra B.,Ramakrishna, Ramesha A.
experimental part, p. 893 - 904 (2012/02/01)
A mild, selective, and green method for the reduction of unsaturated carboxylic acids with sodium borohydride-Raney nickel (W6) system in water is reported. This method is practical and safe and avoids use of organic solvents. Taylor & Francis Group, LLC.
Unprecedented C-selective interstrand cross-linking through in situ oxidation of furan-modified oligodeoxynucleotides
De Beeck, Marieke Op,Madder, Annemieke
experimental part, p. 796 - 807 (2011/04/15)
Chemical reagents that form interstrand cross-links have been used for a long time in cancer therapy. They covalently link two strands of DNA, thereby blocking transcription. Cross-link repair enzymes, however, can restore the transcription processes, causing resistance to certain anti-cancer drugs. The mechanism of these cross-link repair processes has not yet been fully revealed. One of the obstacles in this study is the lack of sufficient amounts of well-defined, stable, cross-linked duplexes to study the pathways of cross-link repair enzymes. Our group has developed a cross-link strategy where a furan moiety is incorporated into oligodeoxynucleotides (ODNs). These furan-modified nucleic acids can form interstrand crosslinks upon selective furan oxidation with N-bromosuccinimide.We here report on the incorporation of the furan moiety at the 20-position of a uridine through an amido or ureido linker. The resulting modified ODNs display an unprecedented selectivity for cross-linking toward a cytidine opposite the modified residue, forming one specific cross-linked duplex, which could be isolated in good yield. Furthermore, the structure of the formed cross-linked duplexes could be unambiguously characterized.
QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS
-
, (2008/12/06)
The present invention relates to novel quinolones of Formula I that inhibit inducible NOS synthase together with methods of synthesizing and using the compounds including methods for inhibiting or modulating nitric oxide synthesis and/or lowering nitric oxide levels in a patient by administering the compounds for the treatment of disease.
Probing structural effects on replication efficiency through comparative analyses of families of potential self-replicators
Kassianidis, Eleftherios,Pearson, Russell J.,Philp, Douglas
, p. 8798 - 8812 (2007/10/03)
A formidable synthetic apparatus for the creation of nanoscale molecular structures and supramolecular assemblies through molecular structures can potentially be created from systems that are capable of parallel automultiplication (self-replication). In order to achieve this goal, a detailed understanding of the relationship be tween molecular structure and replication efficiency is necessary. Diastereoisomeric templates that are capable of specific and simultaneous autocatalysis have been synthesised. A systematic experimental and theoretical evaluation of their behaviour and that of structurally-related systems reveals the key determinants that dictate the emergence of self-replicative function and defines the structural space within which this behaviour is observed.
Heteroaromatic side-chain analogs of pregabalin
Schelkun, Robert M.,Yuen, Po-Wai,Wustrow, David J.,Kinsora, Jack,Su, Ti-Zhi,Vartanian, Mark G.
, p. 2329 - 2332 (2007/10/03)
A series of heteroaromatic analogs of pregabalin has been identified that possess anticonvulsant activity in the DBA/2 mouse model. The methods of synthesis and preliminary pharmacology are discussed herein.
Fine-tuning furan toxicity: Fast and quantitative DNA interchain cross-link formation upon selective oxidation of a furan containing oligonucleotide
Halila, Sami,Velasco, Trinidad,De Clercq, Pierre,Madder, Annemieke
, p. 936 - 938 (2007/10/03)
Oligonucleotides containing a furan modified internal nucleoside have been synthesized; selective in situ oxidation of the furan moiety to a reactive enal species in the presence of a complementary DNA strand gives rise to fast and efficient formation of an interstrand cross-link. The Royal Society of Chemistry 2005.
