Original scientific paper

β-Methyl-D-glucofururonohydroxamic Acid, the First Sugar-Hydroxamic Acid and its Iron(III) Complexes in Solution

Stanko Uršić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, A. Kovačića 1, Croatia
Branka Zorc ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, A. Kovačića 1, Croatia
Viktor Pilepić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, A. Kovačića 1, Croatia
Dražen Vikić-Topić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, A. Kovačića 1, Croatia

Abstract

/J-methyl-D-glucofururonohydroxamic acid sodium salt, the first sugar- hydroxamic acid was synthesized starting from y-lactone of /?-methyl-D- glucofururonoside and characterized by its physical properties and l3C NMR and IR spectral data. Investigation of the coordination ability of /J-methyl- D-glucofururonohydroxamic acid toward the iron(III) in solution reveals the existance of sequential complexation reactions, giving mono-, bis- and tris- (hydroxamato)iron(III) complexes. The equilibrium quotients Qn for the formation of iron(III) complexes with /J-methyl-D-glucofururonohydroxamic acid in solution and at ionic strength of 2.0 M (NaC104 or NaNOs) were determined. The equilibrium quotients Q„, defined as Qn = [FeLn]<3_n) + [H + ]n/[Fe3 + ] [HL]" are as follows: Q,, 34.59 (0.34); Q2, 206.20 (14.86) and Q3, 0.019 (0.007). The values of Amax and the molar absorption coefficient at Amax in visible spectra of mono- and trìs-/?-methyl-D-glucofururonohydro- xamato complexes are 495 nm and 1067(4) mol-1 dm3 cm-1 and 425 nm and 2680 moh1 dm3 cm-1, respectively. These figures are very similar to the corresponding values for the other aliphatic hydroxamate.

Keywords

Hrčak ID:

137143

URI

https://hrcak.srce.hr/137143

Publication date:

29.1.1993.

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