New PDF release: Biomedical Frontiers of Fluorine Chemistry

By Iwao Ojima, James R. McCarthy, John T. Welch

ISBN-10: 084121588X

ISBN-13: 9780841215887

ISBN-10: 0841234426

ISBN-13: 9780841234420

content material: fresh advances within the biomedicinal chemistry of fluorine-containing compounds / Kenneth L. Kirk and Robert Filler --
useful synthesis of enantiopure fluoroamino acids of organic curiosity by means of uneven aldol reactions / V.A. Soloshonok --
Synthesis and incorporation of [alpha]-trifluoromethyl-substituted amino acids into peptides / Beate Koksch, Norbert Sewald, Hans-Dieter Jakubke, and Klaus Burger --
Trifluoromethylated amino alcohols : new man made techniques and medicinal goals / Jean-Pierre Bégué and Danièle Bonnet-Delpon --
uneven synthesis of functionalized fluorinated cyclopropanes and its software to fluoromethano amino acids / Takeo Taguchi, Akira Shibuya, and Tsutomu Morikawa --
Synthesis and homes of novel fluoroprostacyclins : powerful and sturdy prostacyclin agonists / Yasushi Matsumura, Takashi Nakano, Tomoyuki Asai, and Yoshitomi Morizawa --
instruction of fluorinated amino acids with tyrosine phenol lyase : results of fluorination on response kinetics and mechanism of tyrosine phenol lyase and tyrosine protein kinase Csk / R.L. VonTersch, F. Secundo, R.S. Phillips, and M.G. Newton --
effective man made routes to chiral 6-deoxy-6,6,6-trifluorosugars through intramolecular 1,2-O, O-silyl migration / Takashi Yamazaki, Kenji Mizutani, and Tomoya Kitazume --
Fluoroamino acid containing analogues of folic acid and methotrexate / Takashi Tsukamoto, James ok. Coward, and John J. McGuire --
Fluoro-olefin isosteres as peptidomimetics / J.T. Welch, J. Lin, L.G. Boros, B. DeCorte, okay. Bergmann, and R. Gimi --
Molecular layout of fluorine-containing peptide mimetics / Piotr Cieplak, Peter A. Kollman, and Jan P. Radomski --
Mechanistic reports of the prenyl move response with fluorinated substrate analogs / C. Dale Poulter --
Elucidation of the mechanism of inhibition of human immunodeficiency virus 1 protease through difluorostatones / D. Schirlin, J.M. Rondeau, B. Podlogar, C. Tardif, C. Tarnus, V. Van Dorsselaer, and R. Farr --
Fluorine-containing peptidomimetics as inhibitors of aspartyl proteases / Hing L. Sham --
Inhibition of ornithine aminotransferase : a brand new goal for healing intervention / J.B. Ducep, okay. Jund, B. Lesur, S. Sarhan, M. Schleimer, P.R. Zimmermann, and N. Seiler --
Fluorinated diet D₃ analog with in vivo anticancer job / Katsuhiko Iseki and Yoshiro Kobayashi --
Syntheses, organic job, and conformational research of fluorine-containing taxoids / Iwao Ojima, Scott D. Kuduk, John C. Slater, Rayomand H. Gimi, Chung Ming solar, Subrata Chakravarty, Michele Ourevitch, Ahmed Abouabdellah, Danièle Bonnet-Delpon, Jean-Pierre Bégué, Jean M. Veith, Paula Pera, and Ralph J. Bernacki --
layout of a fluoro-olefin cytidine nucleoside as a bioprecursor of a mechanism-based inhibitor of ribonucleotide reductase / James R. McCarthy, Prasad S. Sunkara, Donald P. Matthews, Alan J. Bitonti, Esa T. Jarvi, Jeffrey S. Sabol, Robert J. Resvick, Edward W. Huber, Wilfred A. van der Donk, Guixue Yu, and JoAnne Stubbe --
Synthesis and organic job of 2',2'-difluorodeoxycytidine (gemcitabine) / L.W. Hertel, J.S. Kroin, C.S. Grossman, Gerald B. Grindey, A.F. Dorr, A.M.V. Storniolo, W. Plunkett, V. Gandhi, and P. Huang --
Fluorinated sugars as probes of glycosidase mechanisms / Mark Namchuk, Curtis Braun, John D. McCarter, and Stephen G. Withers --
¹⁹F-labeled amino acids as structural and dynamic probes in membrane-associated proteins / Zhen-Yu solar, E. Ann Pratt, and Chien Ho --
Fluorinated amino acids in nerve platforms / Kenneth L. Kirk and Jun-Ying Nie --
¹⁸F-labeled tracers for positron emission tomography reports within the neurosciences / Yu-Shin Ding and Joanna S. Fowler.

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Acad. Sci. USA 1989, 86, 5600-5604. ; Rao, Y. ; Premchandran, R. ; Haluska, P. ; Fried, J. J. Am. Chem. Soc. 1992, 114, 8464-8472. ; Johns, D. ; Driscoll, J. -C. Biochem. Pharmacol. 1994, 48, 1477-1481. ; Driscoll, J. ; Johns, D. G. Biochem. Pharmacol. 1995, 50, 274-276. Poulter, C. ; Rilling, H. Acc. Chem. Res. 1979, 11, 307-313. Kim, D. ; Lees, W. ; Walsh, C. T. J. Am. Chem. Soc. 1994, 116, 6478-6479. Kim, D. ; Lees, W. ; Haley, T. ; Walsh, C. T. J. Am. Chem. Soc. 1995, 117, 14941502. Kim, D.

The reasons behind this surprising stereoselectivity, brought about by fluorine, is not yet clear. Both steric and electronic factors fail to rationalize the phenomenon (51). One explanation, supported by molecular mechanics calculations, assumes an electrostatic attraction between the partially positively charged Ni(II) and the perfluoroalkyl group, determining the {$-(S)-absolute configuration of the amino acid moiety and, on the other hand, electrostatic repulsion between perfluoroalkyl and carboxy groups, fixing a synFigure 8.

33. ; Kitazume, T. Bioorg. Med. Chem. Lett. 1991, 1, 271. 34. Sting, A. ; Seebach, D. Tetrahedron 1996, 52, 279. 35. ; Miller, D. ; Weber, T. Helv. Chim. Acta 1987, 70, 237. 36. ; Seebach, D. Liebigs Ann. Chem. 1991, 1067. 37. Williams, R. M. 7 of Organic Chemistry Series; Baldwin, J. ; Magnus, P. ; Pergamon Press: Oxford, 1989. 38. Duthaler, R. O. Tetrahedron 1994, 50, 1539. 39. Belokon', Yu. N. Pure Appl. Chem. 1992, 64, 1917. 40. Belokon', Yu. ; Maleev, V. ; Vitt, S. ; Ryzhov, M. ; Kondrashov, Y.

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Biomedical Frontiers of Fluorine Chemistry by Iwao Ojima, James R. McCarthy, John T. Welch


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