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Apratoxin A
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Apratoxin A : ウィキペディア英語版
Apratoxin A

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Apratoxin A - is a cyanobacterial secondary metabolite, known as a potent cytotoxic marine natural product.〔Doi, T.; Numajiri, Y.; Munakata, A.; Takahashi, T.; Org. Lett., 2006, 8, 531-534〕〔Grindberg, R.V.; Ishoey, T.; Brinza, D.; Esquenazi, E.; Coates, R.C.; Liu, W.; Gerwick, L.; Dorrestein, P.G.; Pevzner, P.; Lasken, R.; Gerwick, W.H.; PLOS ONE, 2011, 6, 1-12〕〔Liu, Y.; Law, B.K.; Luesch, H.; Mol. Pharm., 2009, 76, 91-104〕〔Luesch, H.; Chanda, S.K.; Raya, R.M.; De Jesus, P.D.; Orth, A.P.; Walker, J.R.; Belmonte, J.C.I.; Shultz, P.G.; Nat. Chem. Bio., 2006, 2, 158-167〕〔Luesch, H.; Yoshida, W.Y.; Moore, R.E.; Paul, V.J.; Corbett, T.H.; J. Am. Chem. Soc., 2001, 123, 5418-5423〕〔Magarvey, N.A.; Beck, Z.Q.; Golakoti, T.; Ding, Y.; Huber, U.; Hemscheidt, T.K.; Abelson, D.; Moore, R.E.; Sherman, D.H.; ACS Chem. Bio., 2006, 1, 766-779〕 It is a derivative of the Apratoxin family of cytotoxins.〔 The mixed peptide-polyketide natural product comes from a polyketide synthase/non-ribosomal peptide synthase pathway (PKS/NRPS). This cytotoxin is known for inducing G1-phase cell cycle arrest and apoptosis.〔 This natural product's activity has made it a popular target for developing anticancer derivatives.
==Structural Characteristics and Determination==
Apratoxin A is a mixed peptide-polyketide cyclic structure, as shown above. It has a thiazoline ring flanked by polyketide segments, one of which has an unusual methylation pattern. The structure has been elucidated by spectral analysis, including several 2D NMR techniques. The absolute configuration of the amino acid segments was determined by chiral HPLC analysis.〔

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