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Karbacukry (pseudocukry) i cyklofellitole

Identyfikatory
Warianty tytułu
EN
Carba-sugars (pseudosugars) and cyclofellitols
Języki publikacji
PL
Abstrakty
EN
Investigations into carba-sugars have been initiated by McCasland in 1966. Studies in this area have subsequently been continued by Suami and Paulsen , whereas cyclophellitols were investigated by a Japanese team headed by Umezawa. By now, cyclophellitols are also studied by Jung, Roberts and Ziegler. The first chapter of this review paper deals with the definition of carba-sugars and reports on first syntheses of the compounds. The second chapter is devoted to the detection of carba-sugars in Nature, their structure and biological activity. The structure and antibiotic/inhibitory activities have been presented of such carba-sugars as validamycins A and E, validamine, acarbose, trestatine B, amylostatine, valiolamine, validatol and other representatives of this group of compounds including prostaglandins. Induction of a sweet taste by carba-sugars based on the triangle of sweetness has been discussed. The third chapter deals with the common methods of synthesis of carba-sugars. These are as follows: - those based on the Diels-Alder cycloaddition; - syntheses of carba-sugars from inositols; - transformation of one carba-sugar into another by chemical modification of its molecule; - syntheses from naturally occuring sugars and their derivatives. The fourth chapter is confined to cyclophellitols, the derivatives of pseudosugars containing oxirane ring at positions C-1 and C-2. Their detection, properties and syntheses have been desribed. The thiirane and aziridine analogues of cyclophellitols have been mentioned, as well.
Rocznik
Strony
221--243
Opis fizyczny
schem., bibliogr. 41 poz.
Twórcy
  • Wydział Chemii, Uniwersytet Gdański ul. J. Sobieskiego 18, 80-952 Gdańsk
autor
  • Wydział Chemii, Uniwersytet Gdański ul. J. Sobieskiego 18, 80-952 Gdańsk
  • Wydział Chemii, Uniwersytet Gdański, ul. J. Sobieskiego 18, 80-952 Gdańsk
Bibliografia
  • [1] G.L. McCasland, S. Furuta, L.J. Durham, J. Org. Chem., 1966, 31, 1516.
  • [2] Nomenclature o f Carbohydrates, Pure Appl. Chem., 1996, 68, 1919.
  • [3] T. Iwasa, H. Yamamoto, M. Shibata, J. Antibiot., 1970, 32, 595.
  • [4] T. Suami, S. Ogawa, K. Nakamoto, I. Kasahara, Carbohydr. Res., 1977, 58, 240.
  • [5] Y. Kameda, N. Asano, M . Yoshikáwa, K. Matsui, J. Antibiot., 1980, 33, 1575.
  • [6] E. Truscheit, W. Frommer, B. Junge, L. Müller, D. Schmidt, W. Wingender, Angew. Chem. Int. Ed. Engl., 1981, 20, 744.
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  • [8] S. Horii, T. Iwasa, E. Mizuta, Y. Kameda, J. Antibiot., 1971, 24, 59.
  • [9] Y. Kameda, N. Asano, M. Yoshikawa, M. Takeuchi, ibid., 1984, 37, 1301.
  • [10] T. Suami, Topics in Current Chemistry, 1990,154, 257.
  • [11] T. Korzybski, Z. Kowszyk-Gindifer, W. Kuryłowicz, Antybiotyki, PAWL, Warszawa 1977.
  • [12] P. Kafarski, B. Lejczak, Chemia bioorganiczna, PWN, Warszawa, 1994, s. 111.
  • [13] R. J. Ferrier, D. Prasit, Pure Appl. Chem., 1983, 55, 565.
  • [14] R. S. Shallenberg, T.E. Acree, Naturę, 1967, 216, 480.
  • [15] R. S. Shallenberg, T.E. Acree, C.Y. Lee, ibid., 1969, 221, 555.
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  • [17] J. Emsley, Przewodnik po chemii życia codziennego, Prószyński i S-ka, Warszawa, 1996, s. 86.
  • [18] T. Suami, S. Ogawa, Adv. Carbohydr. Chem. Błochem., 1990, 48, 21.
  • [19] G.E. McCasland, S. Furuta, L.J. Durham, J. Org. Chem., 1968, 33, 2835.
  • [20] S. Ogawa, M. Ara, T. Kondoh, M. Saitoh, R. Masuda, T. Toyokuni, T. Suam i, Buli. Chem. Soc. Jpn., 1980, 53, 1121.
  • [21] S. Ogawa, N. Chida, T. Suami, Chem. Lett., 1980, 1559.
  • [22] T. Suami, S. Ogawa, T. Ishibashi, I. Kasahara, Buli. Chem. Soc. Jpn., 1976, 49, 1388.
  • [23] G.E. McCasland, S. Furuta, L.J. Durham, J. Org. Chem., 1968, 33, 2841.
  • [24] S. Ogawa, Y. Tsukiboshi, Y. Iwasaki, T. Suami, Carbohydr. Res., 1985,136, 77.
  • [25] S. Ogawa, Y. Iwasawa, T. Suami, Chem. Lett., 1984, 355.
  • [26] S. Ogawa, Y. Iwasawa, T. Nose, T. Suami, S. Ohba, M. Ito, Y. Saito, J. Chem. Soc. Perkin Trans. I, 1985, 903.
  • [27] H. Paulsen, W. von Deyn, W. Röben, Liebigs Ann. Chem., 1984, 433.
  • [28] T. Suami, K. Tadano, Y. Kameda, Y. Iimura, Chem. Lett., 1984, 1919.
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  • [30] S. Atsumi, H. Iinuma, Ch. Nosaka, K. Umezawa, J. Antibiot., 1990, 43, 1579.
  • [31] K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Tetahedr. Lett., 1990, 31, 1171.
  • [32] D. Semeria, M. Philippe, J. M. Delaumeny, A.M. Sepulchre, S.D. Gero, Synthesis, 1983, 710.
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  • [34] M. Nakata, Ch. Chong, Y. Niwata, K. Toshima, K. Tatsuta, J. Antibiot. 1993, 46, 1919.
  • [35] K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Carbohydr. Res., 1991, 222, 189.
  • [36] M. E. Jung, S.W.T. Choe, J. Olg. Chem., 1995, 60, 3280.
  • [37] S. M. Roberts, P.W. Sutton, J. Chem. Soc. Perkin. Thans. 1 ,1995,1499.
  • [38] F. E. Ziegler, Y. Wang, J. Org. Chem., 1998, 63, 426.
  • [39] F. E. Ziegler, Y. Wang, ibid., 1998, 63, 7920.
  • [40] K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, J. Antibiot., 1991, 44, 912.
  • [41] R. R. Schmidt, R. Preuss, Tetrahedr. Lett., 1989, 30, 3409.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS1-0010-0011
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