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Metabolic Isolation, Stereochemical Determination, and Total Synthesis of Predominant Native Cholesteryl
Chia-Chen Chang1, Hau-Ming Jan2, Chieh-Jen Tseng1
1Applied Chemistry Department, National Yang Ming Chiao Tung University, 1001 University Road, Hsinchu City 300093Taiwan, R.O.C.
Abstract:
We report the isolation and stereochemical determination of the predominant native cholesteryl 6-O-phosphatidyl α-glucoside (CPG) from Helicobacter pylori via an integrated biological and chemical strategy. The strategy employed (i) the metabolic isolation of a CPG analogue and (ii) the enzymatic degradation of the analogue to obtain the native lactobacillic acid for the stereochemical determination. The absolute stereochemistry of the acid was found to be 11R and 12S. Using the new stereochemical data, we accomplished the total synthesis of predominant native CPG and other predominant αCG derivatives.
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