6341-07-7Relevant academic research and scientific papers
A derivatization procedure for the simultaneous analysis of iminosugars and other low molecular weight carbohydrates by GC-MS in mulberry (Morus sp.)
Rodríguez-Sánchez,Hernández-Hernández,Ruiz-Matute,Sanz
experimental part, p. 353 - 359 (2011/09/12)
Different derivatization procedures were assayed to simultaneously analyse iminosugars such as deoxynojirimycin (DNJ) or fagomine and other carbohydrates of low molecular weight by gas chromatography coupled to mass spectrometry (GC-MS) in Morus sp. Both oximation + trimethylsilylation and oximation + acetylation allowed the separation of target compounds, whereas trimethylsilyl (TMS) and acetylated derivatives showed several coelutions. Nevertheless, oximation + acetylation were discarded for giving inaccurate results for ketoses due to their incomplete derivatization. Different conditions for the conversion into trimethylsilyl oximes (TMSO) were assayed, the best results being achieved using hexamethyldisilazane with trifluoroacetic acid as silylation agent. Contents of iminosugars (DNJ, fagomine and pipecolic acid derivatives) and other carbohydrates such as mono and disaccharides, myo-inositol and galactinol isomers in mulberry extracts (fruits, leaves and branches) were determined by GC-MS using the TMSO procedure.
Prebiotic carbohydrate synthesis: Zinc-proline catalyzes direct aqueous aldol reactions of α-hydroxy aldehydes and ketones
Kofoed, Jacob,Reymond, Jean-Louis,Darbre, Tamis
, p. 1850 - 1855 (2007/10/03)
Zn-proline catalyzed aldolisation of glycoladehyde gave mainly tetroses whereas in the cross-aldolisation of glycoladehyde and rac-glyceraldehyde, pentoses accounted for 60% of the sugars formed with 20% of ribose. The Royal Society of Chemistry 2005.
Acylic sugar derivatives for GC/MS analysis of 13C-enrichment during carbohydrate metabolism
Price, Neil P. J.
, p. 6566 - 6574 (2007/10/03)
Metabolic profiling with stable-isotope tracers in combination with gas chromatography/mass spectrometry (GC/ MS) is a well-established technique for measuring substrate redistribution within metabolic pathways. This analysis relies on the ability to localize and quantify the fractional incorporation of 13C isotope into each carbon atom of precursor-derived metabolites. In this paper, several carbohydrate derivatization procedures (peracetylation, deuterioalditol acetates, and aldononitrile acetates) are evaluated for the positional isotopic information obtained by gas chromatography/electron impact mass spectrometry (GC/EI-MS). These derivatives have been compared for the quantitative evaluation of 13C distribution into isotopomers of 13C-labeled aldoses and ketoses, and the fragmentation pathways for 15 hexoses, pentoses, and amino sugars of biological origin have been assessed. In addition, a new type of carbohydrate derivative (dialkyldithioacetal acetates) has been developed for GC/MS that retains the charge on the anomeric carbon of the original monosaccharide. Electron impact ionization of these derivatives generates well-resolved base peaks arising from C1-C2 bond cleavage with charge retention at the C1 thiol groups. The dialkyldithioacetal acetates are uniquely well suited for measuring isotopic enrichment into the characteristic anomeric carbon of aldose sugars and will facilitate the global analysis of metabolic flux in carbohydrate pathways.
Studies on Ketoses, 10. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features
Lichtenthaler, Frieder W.,Klotz, Juergen,Flath, Franz-Josef
, p. 2069 - 2080 (2007/10/03)
Acylations of D-fructose are complicated at several levels.The product distribution is determined not only by the rate of equilibration of the crystalline β-p-form in pyridine to the α-p-, β-f, and α-f-tautomers, but also by the distribution of these forms at a given temperature, as well as their individual hydroxyl group.A detailed study of these parameters resulted in the elaboration of new or improved procedures for the practical, straightforward preparation of either acyclic, furanoid, or pyranoid benzoyl and pivaloyl derivatives, as well as cyclocarbamates with 1,2-spiro-annelated and 2,3-bridging oxazolidinone rings.Accordingly, a variety of simple, tautomerically fixed fructose derivatives, most notably those of the α-p, α-f and β-f forms, are now easily accessible for exploitation as versatile enantiopure building blocks.The structure, anomeric configurations and conformations of the various products obtained were determined on the basis of their 1H and 13C NMR data.The furanoid cases required the support of two X-ray structures: the pentabenzoy-α-D-fructofuranose (9) which has an E2 conformation, and the 2,3-cyclocarbamate 25, in which the β-furanose ring adopts a 5E geometry. - Keywords: D-Fructofuranoses; Benzoates; Pivaloates; 1,2- and 2,3-Cyclocarbamates; keto-D-Fructose pentabenzoates; α-D-Fructopyranoses; 1,2-Cycloacetals
