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Tan, Lik Tong
Preferred name
Tan, Lik Tong
Email
liktong.tan@nie.edu.sg
Department
Natural Sciences & Science Education (NSSE)
Personal Site(s)
ORCID
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- PublicationOpen AccessAbsolute stereochemistry of the β-hydroxy acid unit in hantupeptins and trungapeptinsTheβ-hydroxyl amino acid unit is a common structural feature of many bioactive marine cyanobacterial depsipeptides. In this study, the absolute stereochemistry of the β-hydroxyl acid moieties in hantupeptins and trungapeptins were determined through their synthesis and HPLC analysis of the Mosher ester derivatives. Synthesis of two3-hydroxy-2-methyloctanoic acid (Hmoa) stereoisomers, (2S,3R)-Hmoa and (2S,3S)-Hmoa, were achieved using diastereoselective asymmetric method and the retention times of all four Hmoa isomers were established indirectly by RPLC-MS analysis of their Mosher ester derivative standards. Based on the retention times of the standards, the absolute configuration of the Hmoa unit in hantupeptin C (3) and trungapeptin C (6) was assigned as (2R,3S)- and (2S,3R)-Hmoa, respectively. The use of the Mosher's reagents, coupled with HPLC analysis, provided a viable alternative to the absolute stereochemical determination of -hydroxy acid units in depsipeptides.
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