71051-83-7Relevant academic research and scientific papers
Synthesis of bifunctionalized nitroxyls via intramolecular epoxide ring opening
Ozhogina, Olga A
, p. 553 - 555 (2002)
The syntheses of nitroxyl oxirane and further functionalized derivatives are described. Ring-cleavage reactions of this epoxide have been carried out with a variety of nucleophiles in order to show the general synthetic utility for preparing nitroxyls bearing two functional groups. The relatively facile synthesis of the nitroxyl amino alcohol should prove to be valuable in various spin labeling applications.
Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid
Kumamoto, Takuya,Suzuki, Kazuya,Kim, Sang-Kook,Hoshino, Katsuyoshi,Takahashi, Masahiro,Sato, Hiromi,Iwata, Hiroki,Ueno, Koichi,Fukuzumi, Masahiro,Ishikawa, Tsutomu
body text, p. 2109 - 2114 (2011/02/17)
Nitroxyl-aziridine hybrid, a candidate for a magnetic resonance imaging (MRI) probe and an anticancer drug, was synthesized by aziridine formation reaction of nitroxyl-introduced aldehyde and guanidinium ylide in good diastereoselectivity. The relative co
Improvement of a critical intermediate step in the synthesis of a nitroxide-based spin-labeled deoxythymidine analog
Powell, Jeannine H.,Johnson II, Edward M.,Gannett, Peter M.
, p. 1244 - 1250 (2007/10/03)
Methods to reduce the carboxylic acid moiety in 3-carboxy-2,2,5,5- tetramethyl-pyrrolin-1-oxyl to an alcohol as an intermediate toward the corresponding aldehyde have been explored and an improved method has been developed.
Facile synthesis of 3-formyl-2,2,5,5-tetramethyl-1-oxypyrroline
Stork, Sebastian W.,Makinen, Marvin W.
, p. 1309 - 1312 (2007/10/03)
The spin-label compound 3-formyl-2,2,5,5-tetramethyl-1-oxypyrroline was synthesized from inexpensive starting materials in a sequence of four experimentally undemanding, but high yield achieving transformations. The key step is reduction of an N-methoxy-N-methylcarboxamide to an aldehyde functionality.
Synthesis of nitroxide containing polyenes: two chemically modified retinals and their interaction with bacterioopsin
Groesbeek, M.,Lugtenburg, J.
, p. 403 - 409 (2007/10/03)
The synthesis and spectroscopic characterization of two retinal analogues is described, the paramagnetic 3-pyrrolin-1-yloxy analogue 1 and its diamagnetic equivalent, the 3-pyrroline analogue 2.Various aspects of the synthesis of the aminoxy group containing polyenes are discussed.Upon interaction with bacterioopsin, both 1 and 2 are incorporated in the protein and form a system with λmax 459 nm.Neither of the two bacteriorhodopsin analogues is photoactive.ESR spectroscopy data of the system containing 1 show that the ring part of the chromophore in the protein is rigidly fixed in orientation.
Synthesis of conjugated polyene carbonyl derivatives of nitroxyl spin-labels and determination of their molecular structure and conformation by electron nuclear double resonance
Mustafi, Devkumar,Boisvert, William E.,Makinen, Marvin W.
, p. 3674 - 3682 (2007/10/02)
Formic, propenoic, and pentadienoic acid derivatives of the nitroxyl spin-label 2,2,5,5-tetramethyl-1-oxypyrroline and their corresponding ethyl ester and aldehyde analogues have been synthesized and characterized by chemical methods. Because the π-bonding Orbitals of the olefinic side chains are conjugated to the vinyl group of the oxypyrrolinyl ring, these spin-labeled derivatives are excellent spectrophotometric probes, exhibiting high molecular absorption extinction in the near ultraviolet. The molecular structures and conformations of these spin-labeled derivatives have been determined by electron nuclear double resonance (ENDOR) spectroscopy and molecular modeling. ENDOR was performed on frozen, glassy solutions of the spin-labels, and ENDOR absorptions of protons on the side chains were assigned by selective deuteration. From the maximum and minimum ENDOR shifts that correspond to the principal hyperfine coupling components, the dipolar hyperfine contributions were calculated to estimate electron-proton separations. The electron-proton distances evaluated over a 4.5-10.5-A? range were associated with less than 3% uncertainty on the basis of ENDOR line widths. Conformational analysis based on torsion angle search calculations, constrained by ENDOR-determined electron-proton separations, showed that the polyene chain has an all planar, trans conformation. In the aldehydes the conformation of the C=O group with respect to the alkene chain is found to be s-trans, while in the acids and esters the -OH and -OC2H5 groups were found to be s-trans, placing the C=O group in an s-cis conformation. The different conformations of the carbonyl group in these compounds are explained on the basis of resonance energy and dipolar interactions of the polyene side chain and the carbonyl or carboxyl group.
Synthesis and Dehydrobromination of α-Bromo Aldehyde and Ketone Nitroxyl Radical Spin Labels
Hankovszky, H. Olga,Hideg, Kalman,Sar, P. Cecilla,Lovas, M. Judit,Jerkovich, Gyula
, p. 59 - 62 (2007/10/02)
Various types of α-bromo aldehyde and ketone derivatives of nitroxyl radicals can be prepared in a selective bromination reaction with pyrrolidone hydrotribromide in the presence of a double bond.The saturated α-bromo aldehydes are dehydrobrominated with
