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Mass spectrometry of aldonic and deoxyaldonic acids as trimethylsilyl derivatives

Göran Petersson (Institutionen för teknisk kemi)
Tetrahedron Vol. 26 (1970), p. 3413-3428.
[Artikel, refereegranskad vetenskaplig]

Open-chain trimethylsilyl derivatives of aldonic and deoxyaldonic acids, which can be prepared from salts of the acids, are well suited for structure determination by mass spectrometry. The study is focussed on aldonic and unbranched monodeoxyaldonic acids, but several dideoxyaldonic and branched deoxyaldonic acids are included. Spectra of the derivatives of glycolic, lactic and hydracrylic acids are discussed.

The structural isomers exhibit interpretable differences, whereas the spectra of the diastereomers are similar. The molecular weight and the number of OH groups can be deduced from the spectra, as well as the position of the “deoxy group” in unbranched deoxyaldonic acids. The most prominent fragmentations are α-cleavages of the carbon chain, frequently followed by rearrangement loss of trimethylsilanol. A structurally significant McLafferty-type rearrangement of a trimethylsilyl group is described. Several types of ions decompose by expulsion of small molecules such as CO, CH2O and CO2.

Nyckelord: hydroxy acids, glyceric acid, pentonic acids, hexonic acids, saccharinic acids

Mass spectrometric identifications of hydroxy acids as described in this article were applied in many studies at the department. Several PhD students did research on the degradation of carbohydrates in experiments modelling technical pulping and bleaching processes. Fractions of hydroxy acids were separated by liquid chromatography and left to final assessments by gas chromatography and mass spectrometry after preparation of trimethylsilyl derivatives.

Denna post skapades 2010-01-30. Senast ändrad 2011-06-20.
CPL Pubid: 111258


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Institutionen för teknisk kemi (1946-1998)


Analytisk kemi

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Gas chromatography - mass spectrometry of sugars and related hydroxy acids as trimethylsilyl derivatives