Artifact-free matrix-assisted laser desorption ionization time-of-flight mass spectra of tert.-butyldimethylsilyl ether derivatives of cyclodextrins used for the synthesis of single-isomer, chiral resolving agents for capillary electrophoresis

W. K. Russell, D. H. Russell, M. B. Busby, A. Kolberg, S. Li, D. K. Maynard, S. Sanchez-Vindas, W. Zhu, Gy Vigh

Research output: Contribution to journalArticle

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Abstract

Artifact-free, high-resolution matrix-assisted laser desorption ionization (MALDI) time-of-flight mass spectra have been obtained for the labile, single-isomer, tert.-butyldimethylsilyl ether derivatives of α-, β- and γ-cyclodextrins by optimizing the MALDI sample preparation method. 2,5-Dihydroxybenzoic acid, a 3:1 mixture of 2,5-dihydroxybenzoic acid and 1-hydroxyisoquinoline, and 2,4,6-trihydroxyacetophenone were investigated as MALDI matrices with methanol and acetonitrile as matrix solvents. Partial-to-complete loss of the tert.-butyldimethylsilyl groups was observed when the commonly used 2,5-dihydroxybenzoic acid was the MALDI matrix and/or methanol was the solvent, both with and without trifluoroacetic acid as additive. Loss of the labile tert.-butyldimethylsilyl groups was avoided with 2,4,6-trihydroxyacetophenone as MALDI matrix and acetonitrile as matrix solvent. Good ion intensities were achieved for the (M+Na)+ and (M+K)+ quasimolecular ions in the positive-ion mode. Minor byproducts were observed in some of the samples and the information was used to aid the optimization of the synthetic work.

Original languageEnglish (US)
Pages (from-to)325-330
Number of pages6
JournalJournal of Chromatography A
Volume914
Issue number1-2
DOIs
StatePublished - Apr 20 2001
Externally publishedYes

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Keywords

  • Carbohydrates
  • Cyclodextrins
  • Matrix-assisted laser desorption ionization mass spectrometry
  • tert.-butyldimethly-silylcyclodextrins

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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