108-53-2Relevant academic research and scientific papers
One-pot synthesis of meridianins and meridianin analogues via indolization of nitrosoarenes
Tibiletti, Francesco,Simonetti, Marco,Nicholas, Kenneth M.,Palmisano, Giovanni,Parravicini, Matteo,Imbesi, Federico,Tollari, Stefano,Penoni, Andrea
, p. 1280 - 1288 (2010)
Meridianins, marine alkaloids known as kinase inhibitors with an indole skeleton, and meridianin analogues were produced regioselectively and in moderate to good yields by thermal annulation of nitrosoarenes with 2-amino-4-ethynylpyrimidine and 2-chloro-4-ethynylpyrimidine, respectively, through a novel and atom-economical indolization process.
Fungal and bacterial regioselective hydroxylation of pyrimidine heterocycles
Gotor, Vicente,Quiros, Margarita,Ramon, Liz,Frigola, Jordi,Fernandez, Rosa
, p. 6421 - 6432 (1997)
The bacterium Rhodococcus erythropolis is employed to hydroxylate the anxiolytic lesopitron, and this bacterium, together with Agrobacterium sp. and the fungus Beauveria bassiana, are used to extend the field of hydroxylation of heteroaromatic compounds to a series of unexplored pyrimidines. Of all the substrates investigated, only the carbamate 11a is regioselectively hydroxylated by B. bassiana at the C-5 position of the pyrimidine ring; in contrast, the bacteria are able to regioselectively oxidize, when free, the C-2 and/or C-4 positions of the pyrimidine moiety of all the substrates 1a - 12a up to a maximum of two oxidations.
A Global Scale Scenario for Prebiotic Chemistry: Silica-Based Self-Assembled Mineral Structures and Formamide
Saladino, Raffaele,Botta, Giorgia,Bizzarri, Bruno Mattia,Di Mauro, Ernesto,Garcia Ruiz, Juan Manuel
, p. 2806 - 2811 (2016/06/01)
The pathway from simple abiotically made organic compounds to the molecular bricks of life, as we know it, is unknown. The most efficient geological abiotic route to organic compounds results from the aqueous dissolution of olivine, a reaction known as serpentinization (Sleep, N.H., et al. (2004) Proc. Natl. Acad. Sci. USA 101, 12818-12822). In addition to molecular hydrogen and a reducing environment, serpentinization reactions lead to high-pH alkaline brines that can become easily enriched in silica. Under these chemical conditions, the formation of self-assembled nanocrystalline mineral composites, namely silica/carbonate biomorphs and metal silicate hydrate (MSH) tubular membranes (silica gardens), is unavoidable (Kellermeier, M., et al. In Methods in Enzymology, Research Methods in Biomineralization Science (De Yoreo, J., Ed.) Vol. 532, pp 225-256, Academic Press, Burlington, MA). The osmotically driven membranous structures have remarkable catalytic properties that could be operating in the reducing organic-rich chemical pot in which they form. Among one-carbon compounds, formamide (NH2CHO) has been shown to trigger the formation of complex prebiotic molecules under mineral-driven catalytic conditions (Saladino, R., et al. (2001) Biorganic & Medicinal Chemistry, 9, 1249-1253), proton irradiation (Saladino, R., et al. (2015) Proc. Natl. Acad. Sci. USA, 112, 2746-2755), and laser-induced dielectric breakdown (Ferus, M., et al. (2015) Proc Natl Acad Sci USA, 112, 657-662). Here, we show that MSH membranes are catalysts for the condensation of NH2CHO, yielding prebiotically relevant compounds, including carboxylic acids, amino acids, and nucleobases. Membranes formed by the reaction of alkaline (pH 12) sodium silicate solutions with MgSO4 and Fe2(SO4)3·9H2O show the highest efficiency, while reactions with CuCl2·2H2O, ZnCl2, FeCl2·4H2O, and MnCl2·4H2O showed lower reactivities. The collections of compounds forming inside and outside the tubular membrane are clearly specific, demonstrating that the mineral self-assembled membranes at the same time create space compartmentalization and selective catalysis of the synthesis of relevant compounds. Rather than requiring odd local conditions, the prebiotic organic chemistry scenario for the origin of life appears to be common at a universal scale and, most probably, earlier than ever thought for our planet.
Meteorites as catalysts for prebiotic chemistry
Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
, p. 16916 - 16922 (2014/01/06)
From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
Synthesis and degradation of nucleic acid components by formamide and iron sulfur minerals
Saladino, Raffaele,Neri, Veronica,Crestini, Claudia,Costanzo, Giovanna,Graciotti, Michele,Di Mauro, Ernesto
experimental part, p. 15512 - 15518 (2009/03/12)
We describe the one-pot synthesis of a large panel of nucleic bases and related compounds from formamide in the presence of iron sulfur and iron-copper sulfur minerals as catalysts. The major products observed are purine, 1H-pyrimidinone, isocytosine, adenine, 2-aminopurine, carbodiimide, urea, and oxalic acid. Isocytosine and 2-aminopurine may recognize natural nucleobases by Watson-Crick and reverse Watson-Crick interactions, thus suggesting novel scenarios for the origin of primordial nucleic acids. Since the major problem in the origin of informational polymers is the instability of their precursors, we also investigate the effects of iron sulfur and iron-copper sulfur minerals on the stability of ribooligonucleotides in formamide and in water. All of the iron sulfur and iron-copper sulfur minerals stimulated degradation of RNA. The relevance of these findings with respect to the origin of informational polymers is discussed.
Self-assembling dyes
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, (2008/06/13)
A novel dye according to formula (I): capable of self-assembling thus forming supra-molecular structures. These self-assembling dyes may be advantageously used in an ink-jet ink for improving the stability of ink-jet ink images to light fading.
Ink composition containing a particular type of dye, and corresponding ink jet printing process
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, (2008/06/13)
An ink composition is disclosed which contains a novel type of dye (DYE)n(SAU)m that is capable of self-assembling under appropriate conditions, or is capable of assembling with another analogous dye (DYE′)n′(SAU′)m′, or is capable of assembling with a compound (SAU″)p(X)q, thus forming supramolecular structures. Also disclosed is an ink jet printing process using these novel dyes, and an ink jet printing apparatus provided with an ink cartridge containing such a dye.
2′-Deoxyuridine and 2′-deoxyisocytidine as constituents of DNA with parallel chain orientation: The stabilization of the iCd·Gd base pair by the 5-methyl group
Seela, Frank,He, Yang
, p. 2527 - 2540 (2007/10/03)
Parallel-stranded oligonucleotides containing 2′-deoxyuridine (2) and 2′-deoxyisocytidine (4) were synthesized. The phosphoramidite 11 employed in the solid-phase synthesis carries a (dimethylamino)methylidene residue as amino-protecting group. This group stabilizes the acid-labile glycosylic bond of 4 and enables the base-catalyzed deprotection of oligonucleotides without degrading the nucleoside 4 residues. Oligonucleotide duplexes incorporating the 5-Me derivatives of 2 (→2′-deoxythymidine) and 4 (→2′-deoxy-5-methylisocytidine), which are more stable than those containing the unmethylated nucleosides, were also compared. Depending on the nearest-neighbor environment. Me groups provide an additional stabilization through Me/Me contacts or Me/backbone interactions.
Combined matrix-isolation FT-IR and ab initio 6-31++G** study of H-bonded complexes between water and molecules modelling cytosine or isocytosine
Smets, Johan,Adamovicz, Ludwik,Maes, Guido
, p. 113 - 130 (2007/10/02)
A step-by-step experimental and ab initio SCF/6-31++G** procedure is described for the interpretation of the matrix FT-IR spectra of H-bonded complexes of cytosine or isocytosine with water.The method involves a detailed study of several compounds, each modelling one or a few cytosine sites and/or tautomers in order of increasing complexity.Results are presented for tautomerization processes in 2-OH-pyridine, 4-OH-pyrimidine and isocytosine, and for H-bonded complexes of water with pyrimidine, 4-OH-pyridine and 4-NH2-pyridine.The whole series of obtained results has allowed the setting up of a large-scale vibration correlation diagram for water complexed with N- and O-bases.It also allows some new, important conclusions to be drawn about the major problem of scaling ab initio predicted frequencies for anharmonic proton-donor vibrational modes.
