292
D. Toczek et al.
15. Saladini M, Menabue L, Ferrari E (2001) Sugar complexes with metal
2 +
ions: thermodynamic parameters of associations of Ca
2 +
, Mg
2 +
and Zn
2 +
with galactaric acid. Carbohydr
Res 336(1):55–61. doi:10.1016/S0008-6215(01)00243-9
16. Yang L, Su Y, Liu W, Jin X, Wu J (2002) Sugar interaction with metal ions. The coordination
behavior of neutral galactitol to Ca(II) and lanthanide ions. Carbohydr Res 337(14):1485–
1493. doi:10.1016/S0008-6215(02)00130-1
17. Angyal SJ (1973) Complex formation between sugars and metal ions. Pure Appl Chem
35(2):131–146. doi:10.1351/pac197335020131
18. Angyal SJ (1980) Haworth memorial lecture. Sugar–cation complexes—structure and applications. Chem Soc Rev 9(4):415–428. doi:10.1039/CS9800900415
19. Alvarez AM, Morel-Desrosiers N, Morel J-P (1987) Interactions between cations and sugars.
III. Free energies, enthalpies, and entropies of association of Ca
2 +
, Sr
2 +
, Ba
2 +
, La
3 +
, Gd
3 +
with D-ribose in water at 25 °C. Can J Chem 65(11):2656–2660. doi:10.1139/v87–439
20. Angyal SJ (1974) Complexing of polyols with cations. Tetrahedron 30(12):1695–1702.
doi:10.1016/S0040-4020(01)90691-X
21. Hancock RD, Hegetschweiler K (1993) A molecular mechanics study of the complexation of
metal ions by inositols. J Chem Soc Dalton Trans 2137–2140. doi:10.1039/DT9930002137
22. Palma M, Pascal YL (1995) Étude théorique de la complexation des cations Pb
2 +
et Hg
2 +
par
le d-talose. Can J Chem 73(1):22–40. doi:10.1139/v95-005
23. Dheu-Andries ML, Perez S (1983) Geometrical features of calcium–carbohydrate interactions. Carbohydr Res 124(2):324–332. doi:10.1016/0008-6215(83)88468-7
24. Beevers CA, Cochran W (1947) The crystal structure of sucrose sodium bromide dihydrate.
Proc R Soc London Ser A 190:257–272.
25. Craig DC, Stephenson NC, Stevens JD (1972) An X-ray crystallographic study of β-dmannofuranose-CaCl 2 · 4H 2 O. Carbohydr Res 22(2):494–495. doi:10.1016/S00086215(00)81309-9
26. Jeffrey GA, Kim HS (1971) The crystal and molecular structure of epinositol. Acta Crystallogr
Sect B: Struct Crystallogr Cryst Chem 27(9):1812–1817. doi:10.1107/S0567740871004837
27. Tajmir-Riahi H-A (1988) Interaction of d-glucose with alkaline-earth metal ions. Synthesis, spectroscopic, and structural characterization of Mg(II)- and Ca(II)-d-glucose adducts
and the effect of metal-ion binding on anomeric configuration of the sugar. Carbohydr Res
183:35–46. doi:10.1016/0008-6215(88)80043-0
28. Ollis J, James VJ, Angyal SJ, Pojer PM (1978) An X-ray crystallographic study of α-dallopyranosyl α-d-allopyranoside·CaCl2 · 5H 2 O (a pentadentate complex). Carbohydr Res
60(2):219–228. doi:10.1016/S0008-6215(78)80029-9
29. Lu Y, Deng G, Miao F, Li Z (2003) Sugar complexation with calcium ion. Crystal structure and FT-IR study of a hydrated calcium chloride complex of d-ribose. J Inorg Biochem
92:487–492. doi:10.1016/S0162-0134(03)00251-4
30. Takashi F, Kazuyuki O, Mitsuru T, Tomoya M (2006) Crystal structure of α,αtrehalose–calcium chloride monohydrate complex. J Carbohydr Chem 25(7):521–532.
doi:10.1080/07328300600966414
31. Cook WJ, Bugg CE (1973) Calcium interactions with d-glucans: crystal structure of α,αtrehalose–calcium bromide monohydrate. Carbohydr Res 31:265–275. doi:10.1016/S00086215(00)86191-1
32. Guo J, Lu Y, Whiting R (2012) Metal–ion interactions with sugars. The crystal structure of CaCl 2 –fructose complex. Bull Korean Chem Soc 33(6):2028–2030. doi:10.5012/
bkcs.2012.33.6.2028
33. Yang L, Su Y, Xu Y, Wang Z, Guo Z, Weng S, Yan C, Zhang S, Wu J (2003) Interactions
between metal ions and carbohydrates. Coordination behavior of neutral erythritol to Ca(II)
and lanthanide Ions. Inorg Chem 42:5844–5856. doi:10.1021/ic0300464
34. Yang L, Su Y, Liu W, Jin X, Wu J (2002) Sugar interaction with metal ions. The coordination
behavior of neutral galactitol to Ca(II) and lanthanide ions. Carbohydr Res 337(16):1485–
1493. doi:10.1016/S0008-6215(02)00130-1
D. Toczek et al.
15. Saladini M, Menabue L, Ferrari E (2001) Sugar complexes with metal
2 +
ions: thermodynamic parameters of associations of Ca
2 +
, Mg
2 +
and Zn
2 +
with galactaric acid. Carbohydr
Res 336(1):55–61. doi:10.1016/S0008-6215(01)00243-9
16. Yang L, Su Y, Liu W, Jin X, Wu J (2002) Sugar interaction with metal ions. The coordination
behavior of neutral galactitol to Ca(II) and lanthanide ions. Carbohydr Res 337(14):1485–
1493. doi:10.1016/S0008-6215(02)00130-1
17. Angyal SJ (1973) Complex formation between sugars and metal ions. Pure Appl Chem
35(2):131–146. doi:10.1351/pac197335020131
18. Angyal SJ (1980) Haworth memorial lecture. Sugar–cation complexes—structure and applications. Chem Soc Rev 9(4):415–428. doi:10.1039/CS9800900415
19. Alvarez AM, Morel-Desrosiers N, Morel J-P (1987) Interactions between cations and sugars.
III. Free energies, enthalpies, and entropies of association of Ca
2 +
, Sr
2 +
, Ba
2 +
, La
3 +
, Gd
3 +
with D-ribose in water at 25 °C. Can J Chem 65(11):2656–2660. doi:10.1139/v87–439
20. Angyal SJ (1974) Complexing of polyols with cations. Tetrahedron 30(12):1695–1702.
doi:10.1016/S0040-4020(01)90691-X
21. Hancock RD, Hegetschweiler K (1993) A molecular mechanics study of the complexation of
metal ions by inositols. J Chem Soc Dalton Trans 2137–2140. doi:10.1039/DT9930002137
22. Palma M, Pascal YL (1995) Étude théorique de la complexation des cations Pb
2 +
et Hg
2 +
par
le d-talose. Can J Chem 73(1):22–40. doi:10.1139/v95-005
23. Dheu-Andries ML, Perez S (1983) Geometrical features of calcium–carbohydrate interactions. Carbohydr Res 124(2):324–332. doi:10.1016/0008-6215(83)88468-7
24. Beevers CA, Cochran W (1947) The crystal structure of sucrose sodium bromide dihydrate.
Proc R Soc London Ser A 190:257–272.
25. Craig DC, Stephenson NC, Stevens JD (1972) An X-ray crystallographic study of β-dmannofuranose-CaCl 2 · 4H 2 O. Carbohydr Res 22(2):494–495. doi:10.1016/S00086215(00)81309-9
26. Jeffrey GA, Kim HS (1971) The crystal and molecular structure of epinositol. Acta Crystallogr
Sect B: Struct Crystallogr Cryst Chem 27(9):1812–1817. doi:10.1107/S0567740871004837
27. Tajmir-Riahi H-A (1988) Interaction of d-glucose with alkaline-earth metal ions. Synthesis, spectroscopic, and structural characterization of Mg(II)- and Ca(II)-d-glucose adducts
and the effect of metal-ion binding on anomeric configuration of the sugar. Carbohydr Res
183:35–46. doi:10.1016/0008-6215(88)80043-0
28. Ollis J, James VJ, Angyal SJ, Pojer PM (1978) An X-ray crystallographic study of α-dallopyranosyl α-d-allopyranoside·CaCl2 · 5H 2 O (a pentadentate complex). Carbohydr Res
60(2):219–228. doi:10.1016/S0008-6215(78)80029-9
29. Lu Y, Deng G, Miao F, Li Z (2003) Sugar complexation with calcium ion. Crystal structure and FT-IR study of a hydrated calcium chloride complex of d-ribose. J Inorg Biochem
92:487–492. doi:10.1016/S0162-0134(03)00251-4
30. Takashi F, Kazuyuki O, Mitsuru T, Tomoya M (2006) Crystal structure of α,αtrehalose–calcium chloride monohydrate complex. J Carbohydr Chem 25(7):521–532.
doi:10.1080/07328300600966414
31. Cook WJ, Bugg CE (1973) Calcium interactions with d-glucans: crystal structure of α,αtrehalose–calcium bromide monohydrate. Carbohydr Res 31:265–275. doi:10.1016/S00086215(00)86191-1
32. Guo J, Lu Y, Whiting R (2012) Metal–ion interactions with sugars. The crystal structure of CaCl 2 –fructose complex. Bull Korean Chem Soc 33(6):2028–2030. doi:10.5012/
bkcs.2012.33.6.2028
33. Yang L, Su Y, Xu Y, Wang Z, Guo Z, Weng S, Yan C, Zhang S, Wu J (2003) Interactions
between metal ions and carbohydrates. Coordination behavior of neutral erythritol to Ca(II)
and lanthanide Ions. Inorg Chem 42:5844–5856. doi:10.1021/ic0300464
34. Yang L, Su Y, Liu W, Jin X, Wu J (2002) Sugar interaction with metal ions. The coordination
behavior of neutral galactitol to Ca(II) and lanthanide ions. Carbohydr Res 337(16):1485–
1493. doi:10.1016/S0008-6215(02)00130-1