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Apratoxin A, a cyclodepsipeptide isolated from a marine cyanobacterium, demonstrates potent cytotoxicity against cancer cell lines by a unique mechanism. A lactam analogue of apratoxin A, named as amidapratoxin A, was efficiently synthesized over 22 linear steps in 2.1% overall yield for the first time. The further conformation analysis was conducted by NMR techniques and computer-based molecular modeling. The results showed that the orientation of the benzene ring in tyrosine moiety, the iso-butyl in isoleucine moiety and hydroxyl group in Ahtmna moiety are quite different from that of apratoxin A, which might result in a significant decrease of the cytotoxicity. While further investigation is on the way, these results provide increased understanding of conformation-activity relationship for apratoxin family members which is an important complement to structure-activity relationship. |
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