Cyklitole

• Autorzy: Frankowski R. , Maszewski W. , Smiatacz Z.

Warianty tytułu

EN

Cyclitols

• Języki publikacji: PL

Abstrakty

EN

Cyclitols constitute important structural elements of a variety of biologically active compounds, such as aminoglycosides antibiotics, phospholipid inositols referred to as "secondary messengers", and coordination compounds with metals, e.g. platinum, interest in many areas of natural sciences. In spite of the fact that cyclitols have been known since the 18th century, the majority of significant achievements in this field is seen during the late 90-ties of the 20th century. The first section of this review deals with general information on the nomenclature, structural features, configuration and conformation of the cyclitols. The second section is concerned with the occurrence and biological properties of the inositols, in particular of myo-inositol and its derivatives. A mechanism of action of myo-inositol 1,4,5-triphosphate (1,4,5-IP3) as a secondary messenger has been outlined in Scheme 9. The third section discusses the occurrence and biological activity of the other cyclitols of structures illustrated by the formulae in Schemes 10 through 15. The fourth section is confined to aminocyclitols antibiotics. Their names occurrence, mode of action and formulae of main representatives of this class of compounds are summarized in Table 3 and in Figs. 1 through 8. The last section descibes common methods of preparation of the cyclitols. These are as follows: (i) syntheses using sugar precursors; (ii) syntheses utilizing the Diels-Alder cycloaddition (iii) hydrogenation of polyhydroxybenzenes; (iv) molecular modification of known cyclitols.

Słowa kluczowe

PL

cyklitole; budowa chemiczna; pochodne cyklitoli; antybiotyk aminoglikozydowy

EN

cyclitols

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2001
• Tom: [Z] 55, 9-10
• Strony: 821--848
• Opis fizyczny: schem., tab., bibliogr. 57 poz.

Twórcy

autor

Frankowski R.

• Wydział Chemii, Uniwersytet Gdański ul. J. Sobieskiego 18, 80-952 Gdańsk

autor

Maszewski W.

• Wydział Chemii, Uniwersytet Gdański ul. J. Sobieskiego 18, 80-952 Gdańsk

autor

Smiatacz Z.

• Wydział Chemii, Uniwersytet Gdański ul. J. Sobieskiego 18, 80-952 Gdańsk

• Wydział Chemii, Uniwersytet Gdański ul. J.Sobieskiego 18, 80-952 Gdańsk

Bibliografia

• [1] R. Frankowski, Z. Smiatacz, Wiad. Chem., 2001, 55, 221.
• [2] L. Maquenne, Les Sucres et leur Principaux Dérivés, Gauthiers-Villars, Paris 1900.
• [3] S.J. Angyal, P.T. Gilham, J. Chem. Soc., 19 53, 3691.
• [4] H.G. Fletcher, L . Anderson Jr, H.A. Lardy, J. Org. Chem., 1951, 16, 1238.
• [5] T. Postemak, The Cyclitols, Hermann, Paris 1965.
• [6] L. Anderson, Carhohydr. Chem., Biochem., 1972, vol. IA, 519 ; Nomenklatura związków organicznych, PWN, 1979; IUPAC Information Buli., 1968, 32, 5 1; Eur. J. Biochem., 1968, 5, 1, J. Biol. Chem., 1972, 247, 6 13 ; Pure Appl. Chem., 1974, 37, 285.
• [7] R.S. Cahn, C. Ingold, V. Prelog, Angew. Chem., Int. Ed. Engl., 1966, 5, 385.
• [8] J.F. Stodart, Stereochemistry of Carbohydrates, 1971.
• [9] A. Wiśniewski, J. Madaj, Podstawy chemii cukrów, AGRA -ENVIRO Lab, Poznań-Gdańsk 2000, 178.
• [10] B.V.L. Potter, D. Lampe, Angew. Chem. Int. Ed. Engl., 1995, 34, 1933.
• [11] T.W. Rail, E.W. Sutherland, J. Biol. Chem., 1958, 232, 1065.
• [12] R.H. Michell, Biochim. Biophys. Acta, 1975, 415 , 81.
• [13] H. Streb, R.F. Irvine, M .J. Berridge, I. Schulz, Nature, 1983, 306, 67.
• [14] R.F. Irvine, M.J. Berridge, Nature, 1984, 312, 315 .
• [15] C. Schultz, G. Gebauer, T. Metschies, L. Rensing, B. Jastorff, Biochem. Biophys. Res. Comm., 1990 ,166 , 1319 .
• [16] A.M. Cooke, R. Gigg, B.V.L. Potter, J. Chem. Soc., Chem. Commun., 1987, 1525.
• [17] S. Takahashi, T. Kinoshita, M. Takahashi, J. Antibiot., 1993, 47, 95 i 1643.
• [18] T. Desai, J. Gigg, R. Gigg, Carbohydr. Res., 1996, 280, 209.
• [19] N. Moitessier, F. Chretien, Y. Chapleur, C. Humeau, Tetrahedron Lett., 1995, 36, 8023.
• [20] F. Roussel, M. Hilly, F. Chretien, J.P. Mauger, Y. Chapleur, J. Carb. Chem., 1999 ,18 , 697.
• [21] L. Anderson, E.S. De Luca, A. Bieder, G.G. Post, J. Amer. Chem. Soc., 1957, 1171 .
• [22] S.J. Angyal, P.T. Gilham, C.G. Mac Donald, J. Amer. Chem. Soc., 1957 1417 .
• [23] N. Chida, M. Suzuki, M. Suwama, S. Ogawa, J. Carb. Chem., 1989, 8, 319 .
• [24] H. Paulsen, W. von Deyn, Liebigs Ann. Chem., 1987, 141.
• [25] S. Ogawa, A . Isaka, Carbohydr. Res., 19 9 1, 210 , 105.
• [26] N. Chida, T. Tobe, M. Suwama, M. Ohtsuka, S. Ogawa, J. Chem. Soc., Chem. Comm., 1990, 994.
• [27] S. Angyal, L. Anderson, Adv. Carbohydr. Chem., 1959, 14, 200.
• [28] M. Balci, Y. Sütbeyaz, H. Seçen, Tetrahedron, 1990, 46, 37 15 .
• [29] S. Alleman, P. Vogel, Helv. Chim. Acta, 1994, 77, 1.
• [30] T. Suami, Tetsuo, Shiio, Takashi, Chem. Abstr., 1987, 107 , 191010p.
• [31] S. Umezawa, Adv. Carbohydr. Chem. Biochem., 1974, 30, 111 i 183.
• [32] N. Chida, M. Ohtsuka, K. Nakazawa, S. Ogawa, J. Chem. Soc., Chem. Comm., 1989, 436.
• [33] H. Fukami, K. Kitahara, M. Nakajima, Tetrahedron Lett., 1976, 7, 545.
• [34] J. Cleophax, S.D. Gero, E. Jegou-Aumont, J. Leboul, D. Mercier, J. Chem. Soc., Chem. Comm., 1975, 11.
• [35] T. Nara, M. Yamamoto, I. Kawamoto, K. Takayama, R. Okachi, S. Takasawa, T. Sato, S. Sato, J. Antibiot., 1977, 30, 533 i 551.
• [36] T. Deushi, A. Iwasaki, K. Kamiya, T. Kunieda, T. Mizoguchi, M. Nakayama, H. Itoh, T. Mori, J. Antibiot., 1979. 32, 173.
• [37] K. Takeda, K. Aihara, T. Furumai, Y. Ito, J. Antibiot., 1979, 32, 18.
• [38] K. Kanai, I. Nishigaki, T. Taki, S. Ogawa, T. Suami, Carbohydr. Res., 1987, 170, 47.
• [39] K.L. Rinehart Jr., Pure Appl. Chem., 1977, 49, 136 1.
• [40] J.M . Grosheintz, H.O.L. Fisher, J. Amer. Chem Soc., 1948, 70, 1477 i 1479.
• [41] R J . Ferrier, J. Chem. Soc., Perkin Trans. I, 1979, 1455.
• [42] T. Suami, K. Tadano, S. Horiuchi, Bull. Chem. Soc. Jpn., 1975, 48, 2895.
• [43] M. Iwakawa, J. Yoshimura, M. Funabashi, Bull. Chem. Soc. Jpn., 1981, 54, 496.
• [44] J. Kovar, H. Baer, Carbohydr. Res., 1975, 45, 161.
• [45] A .A . Othman, N.A. Al-Masudi, U.S. Al-Timari, J. Antibiot., 1978, 31, 1007.
• [46] M. Funabashi, J. Yoshimura, J. Chem. Soc., Perkin Trans. I, 1979, 1425.
• [47] M. Funabashi, K. Kobayashi, J. Yoshimura, J. Org. Chem., 1979, 44, 1618.
• [48] J. Kovar, H. Baer, Can. J. Chem., 1973, 5 1, 180 1, 2836 i 3373.
• [49] M. Madi-Puskas, I. Pelyvas, R. Bognar, J. Carbohydr. Chem., 1985, 4, 323.
• [50] A.S. Machado, A . Olesker, G. Lukács, Carbohydr. Res., 1985, 135 , 231.
• [51] P. Laszlo, I. Pelyvas, F. Sztaricskai, L. Szilagyi, A. Somogyi, Carbohydr. Res., 1988, 175, 227 .
• [52] B. Beier, K. Schürle, O. Werbitzky, W. Piepersberg, J. Chem Soc., Perkin Trans. I, 1990, 2255.
• [53] Wieland, Wishart, Ber., 19 14 , 47, 2082.
• [54] S.J. Angyal, D J . McHugh, J. Amer. Chem. Soc., 1957, 3682.
• [55] N. Chida, K. Nakazawa, M. Ohtsuka, M. Suzuki, S. Ogawa, Chem. Lett., 1990, 423
• [56] V. Plouvier, Bull. Soc. Chim. Biol., 1963, 45, 1079.
• [57] T. Korzybski, Z. Kowszyk-Gindifer, W. Kurylowicz, Antybiotyki, PZW L, Warszawa 1977.

Uwagi

PL

Opracowane ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).