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Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Design, synthesis and cytotoxicity of bengamide analogues and their epimers
Thi Dao Phi1,2, Huong Doan Thi Mai1, Van Hieu Tran1
1Advanced Center for Bioorganic Chemistry , Institute of Marine Biochemistry , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam . Email: phamvc@imbc.vast.vn ; ; Tel: +84437917049.
Abstract:
Starting from d-glycero-d-gulo-heptonic acid γ-lactone and amino acids, a number of diastereoisomeric bengamide analogues were synthesized. Optimization of the reaction conditions revealed that microwave irradiation assistance is a powerful method for the preparation of aminolactams, as well as for the coupling reactions of the lactone 5 with aminolactams. Cytotoxic activity evaluation against six cancer cell lines (KB, HepG2, LU1, MCF7, HL60, and Hela) demonstrated that the configuration of C-2' seems to be critical for the cytotoxic activity of compounds 8b (2'R) and 8a (2'S). Additionally, comparison of cytotoxicity of the protected acetonide compounds with that of their corresponding deprotected bengamide analogues suggested that the flexibility of the ketide side chain should be required for their cytotoxic activity.
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