201472-73-3Relevant academic research and scientific papers
Partial synthesis of ganglioside and lysoganglioside lipoforms as internal standards for MS quantification
Gantner, Martin,Schwarzmann, Günter,Sandhoff, Konrad,Kolter, Thomas
, p. 2692 - 2704 (2014)
Within recent years, ganglioside patterns have been increasingly analyzed by MS. However, internal standards for calibration are only available for gangliosides GM1, GM2, and GM3. For this reason, we prepared homologous internal standards bearing nonnatural fatty acids of the major mammalian brain gangliosides GM1, GD1a, GD1b, GT1b, and GQ1b, and of the tumor-associated gangliosides GM2 and GD2. The fatty acid moieties were incorporated after selective chemical or enzymatic deacylation of bovine brain gangliosides. For modifi cation of the sphingoid bases, we developed a new synthetic method based on olefi n cross metathesis. This method was used for the preparation of a lyso-GM1 and a lyso-GM2 standard. The total yield of this method was 8.7% for the synthesis of d17:1-lyso-GM1 from d20:1/18:0-GM1 in four steps. The title compounds are currently used as calibration substances for MS quantifi cation and are also suitable for functional studies.
Synthetic libraries of tyrosine-derived bacterial metabolites
Georgiades, Savvas N.,Clardy, Jon
supporting information; experimental part, p. 3117 - 3121 (2009/04/03)
The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters were synthesized in solution-phase.
