24758-69-8Relevant articles and documents
A convenient preparation of aldonohydroxamic acids in water and crystal structure of L-erythronohydroxamic acid
Salmon, Laurent,Prost, Elise,Merienne, Claude,Hardre, Renaud,Morgant, Georges
, p. 195 - 204 (2001)
Hydroxamic acids derived from aldonic acids, namely aldonohydroxamic acids, have become an increasingly important class of inhibitors of enzymes involved in the metabolism of carbohydrates. We now report the straightforward preparation of various types of aldonohydroxamic acids by a new methodology involving the use of commercial 50% aqueous hydroxylamine as the source of the free base hydroxylamine that reacts directly with the corresponding aldonolactone dissolved in water. The reaction proceeds almost instantaneously in water at room temperature, yielding generally pure products in quantitative yield. To date, this methodology is probably the most facile and efficient way to synthesize aldonohydroxamic acids. We also determined by X-ray diffraction analysis the first crystal structure of a free aldonohydroxamic acid reported to date. Crystals of L-erythronohydroxamic acid belonged to the monoclinic system, space group P21, a=5.511(3), b=7.556(1), c=8.071(3) A, β=109.10°, and Z=2.
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.
Hydroxamic acids and hydroxamic acid ethers, and the use thereof as complexing agents
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, (2008/06/13)
Hydroxamic acids and hydroxamic acid ethers I and II STR1 where Z1 and Z2 are --NH --OY, --NR1 --OY or --OX, where in the case of (I) at least one of Z1 or Z2, and in the case of (II) Z1 is --NH --OY or --NR1 --OY, and R1 is C1 -C18 -alkyl, X is hydrogen, alkali metal, ammonium or substituted ammonium, and Y is hydrogen, alkali metal, ammonium, substituted ammonium or C1 -C18 -alkyl, and L is a C1 -C100 linker which can also carry oxygen and nitrogen functional groups, with the exception of N,N-bis(carboxymethyl)-2-aminoacetohydroxamic acid.
