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Synthesis of 1-adamantamine derivatives of mannose and galactose and thermodynamics of complexation with betha-cyclodextrin (CROSBI ID 569602)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa

Ribić, Rosana ; Car, Željka ; Požar, Josip ; Kovačević, Davor ; Petrović Peroković, Vesna Synthesis of 1-adamantamine derivatives of mannose and galactose and thermodynamics of complexation with betha-cyclodextrin // XIII. Ružičkini dani "Danas znanost-sutra industrija" : zbornik radova i sažetaka / Šubarić, Drago (ur.). Osijek: Prehrambeno tehnološki fakultet Sveučilišta Josipa Jurja Strossmayera u Osijeku ; Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2010. str. 28-28

Podaci o odgovornosti

Ribić, Rosana ; Car, Željka ; Požar, Josip ; Kovačević, Davor ; Petrović Peroković, Vesna

engleski

Synthesis of 1-adamantamine derivatives of mannose and galactose and thermodynamics of complexation with betha-cyclodextrin

Protein lectins that specifically bind carbohydrate molecules are key components in cell recognition process and transfer of biological information. It is well known that cyclodextrin molecules are suitable models that contribute to better understanding of the noncovalent interactions. Adamantane derivatives bind well into β-cyclodextrin cavity and adamantyl glycosides also proved to be suitable substrates for further study of these interactions. We present in this work the synthesis of adamantyl glycoconjugates in which adamantyl unit was indirectly connected to monosaccharides mannose or galactose through chiral linkers (methyl esters of (R)- or (S)-3- hydroxypropanoic acid). Linker was connected to monosaccharide molecule through O-glycosidic bond and to 1-adamantamine molecule with amide bond. The complexation of adamantyl glycoconjugates with β-cyclodextrin was studied in water at 25 ºC by means of titration calorimetry. The thermodynamic parameters of complexation, namely reaction enthalpies, standard reaction entropies and binding constants were determined. In the case of all investigated derivates the complexation process was enthalpically controlled. The standard reaction entropy was positive for all examined reactions. In general, the complexation parameters of different adamantyl glycoconjugates and β-cyclodextrin were very similar. It can be concluded that the sugar structure and the configuration of the anomeric carbon and of the stereogenic center of the linker do not influence the complexation thermodynamics significantly.

adamantyl glycoconjugates ; synthesis ; betha-cyclodextrin ; complexation ; thermodynamics

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Podaci o prilogu

28-28.

2010.

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objavljeno

978-953-7005-22-1

Podaci o matičnoj publikaciji

XIII. Ružičkini dani "Danas znanost-sutra industrija" : zbornik radova i sažetaka

Šubarić, Drago

Osijek: Prehrambeno tehnološki fakultet Sveučilišta Josipa Jurja Strossmayera u Osijeku ; Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI)

Podaci o skupu

XIII. Ružičkini dani, DANAS ZNANOST-SUTRA INDUSTRIJA

poster

16.09.2010-17.09.2010

Vukovar, Hrvatska

Povezanost rada

Kemija