Abstract
The biotransformation of organofluorine materials into optically active functionalized fluorinated materials along with a discussion on the effect of fluorine atom(s) during enantioselective and/or diastereoselective transformations is described. The ability of microorganisms to discriminate between enantiomers is particularly important regarding resolution and asymmetric synthesis. Furthermore, the use of chiral fluorinated materials in the design and preparation of new types of biologically active materials is discussed.
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6 References
Filler R, Kobayashi Y (1982) Biomedical aspects of fluorine chemistry. Kodansha & Elsevier Biomedical, Tokyo
Welch JT, Eswarakrishnan S (1991) Fluorine in bioorganic chemistry. John Wiley, New York
Abdel-Aal YAI, Hammock BD (1986) Science 223:1073
Imperiali B, Abeles RH (1987) Biochemistry 26:2682
Mochizuki N, Sugai T, Ohta H (1994) Biosci Biotechnol Biochem 58:1666
Johno M, Itoh K, Lee J, Ouchi Y, Takezoe H, Fukuda A, Kitazume T (1990) Jpn J Appl Phys 29:L107
Koden M, Shiomi M, Nakagawa, K, Funada F, Awane K, Yamazaki T, Kitazume T (1991) Jpn J Appl Phys 30:L1300
Itoh K, Takeda M, Namekawa M, Nayuri S, Murayama Y, Yamazaki T, Kitazume T (1993) Ferroelectrics 148:85
Suzuki Y, Nonaka O, Koide Y, Okabe N, Hagiwara T, Kawamura I, Yamamoto N, Yamada Y, Kitazume T (1993) Ferroelectrics 147:109
Itoh K, Takeda M, Namekawa M, Nayuri S, Murayama Y, Yamazaki T, Kitazume T (1994) Chem Lett. 839. (f) Itoh K, Takeda M, Namekawa M, Nayuri S, Murayama Y, Yamazaki T, Kitazume T (1995) Chem Lett 641
Walba DM, Clark NA et al. (1988) J Am Chem Soc. 110:8686
Kitazume T, Yamazaki T (1991) In: Welch JT (ed) Selective fluorination in organic and bioorganic chemistry, ACS: Washington DC, pp 175
Welch JT, Eswarakrishnan SJ (1987) Am Chem Soc 109:6716
Welch JT, Seper KW (1988) J Org Chem 53:2991
Bravo P, Frigerio M, Fronza G, Ianni A, Resnati G (1990) Tetrahedron 46:997
Crout DHG, Christen M (1989) Modern synthetic methods Scheffold R (ed) Springer, Berlin Heidelberg New York
Guanti G, Banfi L et al. (1986) J Chem Soc Chem Commun 138
Seebach D, Renaud P, Schweizer WB, Züger MF (1984) Helv Chim Acta 67:1843
Servi S (1990) Synthesis 1
Kitazume T, Sato T (1985) J Fluorine Chem 30:189
Kitazume T, Nakayama Y (1987) J Org Chem 51:2795
Kitazume T, Kobayashi T (1987) Synthesis 187
Fearon K, Gelb MH et al. (1987) Chem 30:1617
Takahashi LH, Radhakrishnan R, Rosenfield Jr RE, Meyer Jr EF, Trainor DA (1984) J Am Chem Soc 106:7250
Bernardi R, Cardillo R, Ghiringhelli D, de Pava OVJ (1987) Chem Soc Perkin Trans. 1:1607
Forni A, Moretti I, Prati F, Torre G (1994) Tetrahedron 50:11995
(a) Kitazume T, Asai M, Tsukamoto T, Yamazaki T (1992) J Fluorine Chem 56:271. (b) Kitazume T, Murata K, Ikeya T (1986) J Fluorine Chem 31:143. (c) Kitazume T, Murata K (1987) J Fluorine Chem 36:339. (d) Kitazume T, Asai M, Lin J-T, Yamazaki T (1987) J Fluorine Chem 35:477. (e) Yamazaki T, Asai M, Ohnogi T, Lin J-T, Kitazume T (1987) J Fluori ne Chem 35:537. (f) Kitazume T, Okamura N, Ikeya T (1988) J Fluorine Chem 39:107
Yonazawa T, Sakamoto Y, Nogawa K, Yamazaki T, Kitazume T (1996) Chem. Lett 855
Whitesides GM, Ladner WE (1984) J Am Chem Soc 106:7250
(a) Lin J-T, Yamazaki T, Kitazume T (1987) J Org Chem 52:3211. (b) Kitazume T, Takeda M, Lin J-T, Yamazaki T (1989) Fluorine Chem 43:177. (c) Lin J-T, Takeda M, Yamazaki T, Kitazume T (1989) J Fluorine Chem 44:113. (d) Murata K, Kitazume T (1993) Tetrahedron; Asymmetry 4:889
Yamazaki T, Ichikawa S, Kitazume T (1989) J Chem Soc Chem Commun 253
Yamazaki T, Lin J-T, Takeda M, Kitazume T (1990) Tetrahedron; Asymmetry 1:351
Molander GA, Etter JBJ (1987) J Org Chem 52:3942
Molander GA, Harring LS (1989) J Org Chem 54:3525
Anh NT, Eisenstein O (1977) Nouv J Chim 1:61
Anh NT (1980) Top Current Chem 88:145
Yamazaki T, Okamura N, Kitazume T. (1990) Tetrahedron Asymmetry 1:521
Konno T, Umetani T, Kitazume T (1997) J Org Chem 62:137
Furuhashi K, Shintani M, Takagi M (1986) Appl Microbiol Biotechnol 23:218
Takahashi O, Umezawa J, Furuhashi K, Takagi M (1989) Tetrahedron Lett 30:1583
Takahashi O, Furuhashi K, Fukumasa M, Hirai T (1990) Tetrahedron Lett 31:7031
Yamazaki T, Mizutani K, Takeda M, Kitazume T (1992) J Chem Soc Chem Commun 55
Yamazaki T, Mizutani K, Kitazume T (1993) Tetrahedron Asymmetry 4:1059
Yamazaki T, Mizutani K, Kitazume T (1993) J Org Chem 58:4346
Yamazaki T, Mzutani K, Kitazume T (1995) J Org Chem 60:6046
Takeda M, Ishizuka T, Itoh K, Kitazume T (1995) J Fluorine Chem 75:111
Gaspar J, Guerrero A (1995) Tetrahedron Asymmetry 6:231
Komatsu Y, Sasaki F, Takei S, Kitazume T. Tetrahedron Asymmetry, to be submitted
O’Hagan D, Zaidi NA, Lamout RB (1993) Tetrahedron Asymmetry 4:1703
Kollonitsxh J (1978) Isr J Chem 17: 53 and references cited therein
(a) Yamazaki T, Haga J, Kitazume T (1991) Bio Med Chem Lett 5: 271. (b) Kitazume T, Lin J-T, Yamazaki T (1991) Tetrahedron Asymmetry 2:235
Hanzawa Y, Kawagoe K, Ito M Kobayashi Y (1987) Chem Pharm Bull 35:1633
Keller JW, Hamilton B (1986) J Tetrahedron Lett 27:1249
Greenstein JP, Winitz M (1961) Chemistry of the amino acids, vol II. John Wiley & Sons, New York
Soloshonok VA, Kiritenko AG, Fokina NA, Kukhar VP, Galushko SV, Svedas VK, Resnati G (1994) Tetrahedron Asymmetry 5:1225
Matsumura Y, Urushihara M, Tanaka H, Uchida K, Yasuda A (1993) Chem Lett 1255
Tanaka H, Uchida K, Yamabe M (1986) Centenary of the Discovery of Fluorine. Inter national Symposium Abstract
Nagasawa T, Utagawa T, Goto J, Kim C-J, Tani Y, Kumagai H, Yamada H (1981) Eur J Biochem 117:33
(a) Japan patent 60-34292 (1985). (b) Japan patent 61-296698 (1986)
Miyamoto K, Tsuchiya S, Ohta H (1992) J Fluorine Chem 59:225
Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) J Am Chem Soc 113:4092
Kusumi T, Hamada T, Ishitsuka MO, Ohtani I, Kakisawa H (1992) J Org Chem 57:103
Kusumi T, Hamada T, Hara M, Ishitsuka MO, Ginda H, Kakisawa H (1992) Tetrahedron Lett 33:2019
Kusumi T, Fukushima T, Ohtani I, Kakisawa H (1991) Tetrahedron Lett 32:2939
Ohta H, Miyamae Y, Kimura Y (1989) Chem Lett 379
Feichter C, Faber K, Griengl H (1991) J Chem Soc Perkin Trans 1:653
Matos JR, Smith MB, Wong C-H (1985) Bioorganic Chem 13:121
Wong C-H, Matos JR (1985) J Org Chem 50:1992
Vidal-Cros A, Gaudry M, Marquet A (1989) J Org Chem 54:498
Oelrichs PB, McEwan T (1961) Nature (London) 190:808
Oliverira MM (1963) Experientia 19:586
Lovelace J, Miller GW, Welkie GW (1968) Atoms Environ 2:187
Cheng JYO, Yu MH, Miller GW, Welkie GW (1968) Environ Sci Technol 2:367
Fowden L (1968) Proc Roy Soc 171:5
Rokita SE, Walsh CT (1983) Biochemistry 22:2821
Brandange S, Dahlman O, Morch L (1981) J Am Chem Soc 103:4452
Stallings WC, Monti CT, Belvedere JF, Preston RK, Glusker JP (1980) Arch Biochem Biophys 203:65
Hoving H, Crtsell B, Leadlay PF (1985) Biochemistry 24:6163
Marietta AM, Srere PA, Walsh CT (1981) Biochemistry 20:3719
Sanada M, Miyano T, Iwadare S, Williamson JM, Arison BH, Smith JL, Douglas AW (1986) J Antibiotics 39:259
Brandy K, Wei A, Rihge D, Abeles RH (1990) Biochemistry 29:7600
Fukuda H, Tetsu M, Kitazume T (1996) Tetrahedron 52:157
a) Tsukamoto T, Kitazume T (1990) Synth Communm 20:3181. (b) Tsukamoto T, Kitazume T (1992) J Chem Soc Chem Commun 540
Tsukamoto T, Yoshimura T, Kitazume T (1991) Tetrahedron Asymmetry 2:759
(a) Kitazume T, Sato T, Kobayashi T, Lin J-T (1986) J Org Chem 51:1003. (b) Kitazume T, Kobayashi T (1986) J Fluorine Chem 31:357 (c)
Mohr P, Waespe-Savcevic N, Tamm C, Gawronsca K, Gawronski JK (1983) Helv Chim Acta 66:2501
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Kitazume, T., Yamazaki, T. (1997). Enzymatically Controlled Reactions of Organofluorine Compounds. In: Chambers, R.D. (eds) Organofluorine Chemistry. Topics in Current Chemistry, vol 193. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69197-9_3
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DOI: https://doi.org/10.1007/3-540-69197-9_3
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