Metabolic Isolation, Stereochemical Determination, and Total Synthesis of Predominant Native Cholesteryl Phosphatidyl-α-glucoside from Carcinogenic Helicobacter pylori

Chia Chen Chang, Hau Ming Jan, Chieh Jen Tseng, Soumik Mondal, Andualem Bahiru Abera, Ming Yen Hsieh, Tsai Chen Yang, Sasikala Muthusamy, Sheng Cih Huang, Chun Hung Lin, Kwok Kong Tony Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
JournalOrganic Letters
DOIs
StateAccepted/In press - 2022

Fingerprint

Dive into the research topics of 'Metabolic Isolation, Stereochemical Determination, and Total Synthesis of Predominant Native Cholesteryl Phosphatidyl-α-glucoside from Carcinogenic Helicobacter pylori'. Together they form a unique fingerprint.

Cite this