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Permethylation Linkage Analysis Techniques for Residual Carbohydrates

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Abstract

Permethylation analysis is the classic approach to establishing the position of glycosidic linkages between sugar residues. Typically, the carbohydrate is derivatized to form acid-stable methyl ethers, hydrolyzed, peracetylated, and analyzed by gas chromatography-mass spectrometry. The position of glycosidic linkages in the starting carbohydrate are apparent from the mass spectra as determined by the location of acetyl residues. The completeness of permethylation is dependent upon the choice of base catalyst and is readily confirmed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry mass spectrometry. For the permethylation of β-cyclodextrin, Hakomori dimsyl base is shown to be superior to the NaOH–dimethyl sulfoxide system, and the use of the latter resulted in selective under-methylation of the 3-hydroxy groups. These techniques are highly applicable to residual carbohydrates from biofuel processes.

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Acknowledgment

Jim Nicholson and Trina Hartman (NCAUR-ARS-USDA) are both thanked for their technical assistance.

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  1. USDA-ARS-NCAUR, Bioproducts & Biocatalysis Research Unit, 1815 North University Street, Peoria, IL, 61604, USA

    Neil P. J. Price

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  1. Neil P. J. Price
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Correspondence to Neil P. J. Price.

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Mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture.

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Price, N.P.J. Permethylation Linkage Analysis Techniques for Residual Carbohydrates. Appl Biochem Biotechnol 148, 271–276 (2008). https://doi.org/10.1007/s12010-007-8044-8

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  • DOI: https://doi.org/10.1007/s12010-007-8044-8

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