Stereochemical Assignment of Neocarzinostatin Chromophore. Structures of Neocarzinostatin Chromophore-Methyl Thioglycolate Adducts

Journal of the American Chemical Society

Volumn 110, Issue 21, 1988, Pages 7212-7214

  Myers, Andrew G ^a   Proteau, Philip J ^a   Handel, Tracy M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ZINOSTATIN CHROMOPHORE;

DRUG STRUCTURE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION;

EID: 0023774255     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00229a045     Document Type: Article

References (17)

1. Isolation of neocarzinostatin: Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68.
2. Isolation of 1: (a) Napier, M. A.; Holmquist, B.; Strydom, D. J.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1979, 89, 635. (b) Koide, Y.; Ishii, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342.
3. (a) In determination of structure 1, the C10 and C11 substituents were shown to be trans. The stereochemistry at C4, C5, C10, C11, and C13 was not assigned: Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331. (b) The N-methylfucosamine appendage has been shown unambiguously to be a D-sugar: Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. (c) The stereochemistry at C10 and C11 was recently suggested to be R, R based on a model of the binding of 1 to DNA: Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631.
4. (a) Beerman, T. A.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1974, 59, 1254. (b) Beerman, T. A.; Poon, R.; Goldberg, I. H. Biochim. Biophys. Acta 1977, 475, 294. (c) Kappen, L. S.; Goldberg, I. H. Nucleic Acids Res. 1978, 5, 2959.
5. Hensens, O. D.; Dewey, R. S.; Liesch, J. M.; Napier, M. A.; Reamer, R. A.; Smith, J. L.; Albers-Schonberg, G.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1983, 113, 538.
6. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493.
7. Fesik, S. W.; Olejniczak, E. T. Magn. Reson. Chem. 1987, 25, 1046.
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10. Prepared from indene and 1-chloro-1, 2-ethanediol diacetate [Nagasawa, J.-i.; Araki, Y.; Ishido, Y. J. Org. Chem. 1981, 46, 1734] after the following: Neuenschwander, M.; Vogeli, R.; Fahrni, H.-P.; Lehmann, H.; Ruder, J.-P. Helv. Chim. Acta 1977, 60, 1073.
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13. Stereochemical assignments are based on the Sharpless model for asymmetric-epoxidation: Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
14. Myers, A. G.; Widdowson, K. L., submitted for publication in Tetrahedron Lett.
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17. (a) Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.-i.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461. (b) Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.-i.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.