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note
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Abbreviations: APCI = atmospheric pressure chemical ionization; ESI = electrospray ionization; Fmoc = (9H-fluoren-9-ylmethoxy)-carbonyi; HMQC = heteronuclear multiple quantum correlation spectroscopy; HMBC = heteronuclear multiple bond correlation spectroscopy; Trp = tryptophan; Pro = proline.
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11
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0343559109
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note
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The L-Trp-L-Pro diketopiperazine is itself a fungal natural product, brevianamide F.
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The synthesis of 7 was presented at the 214th ACS National Meeting, Las Vegas, 7-11 Sep 1997, abstract ORGN 282.
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214th ACS National Meeting
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0342688876
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note
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(b) See also ref 12 and 19.
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32
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0343123156
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note
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2H).
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34
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0001092045
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36
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0015538314
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Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
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37
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0021952743
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Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
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38
-
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0343995261
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Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
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39
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0032143275
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These assays were performed by Professor Osada's group, according to published methods, ref 3, and: (a) Usui, T.; Kondoh, M.; Cui, C.-B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543-548. (b) Kondoh, M.; Usui, T.; Mayumi, T.; Osada, H. J. Antibiot. 1998, 5, 801-804.
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Osada, H.5
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40
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0031687689
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These assays were performed by Professor Osada's group, according to published methods, ref 3, and: (a) Usui, T.; Kondoh, M.; Cui, C.-B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543-548. (b) Kondoh, M.; Usui, T.; Mayumi, T.; Osada, H. J. Antibiot. 1998, 5, 801-804.
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41
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0343123154
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note
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Note Added in Proof. After submission of this paper, we have learned of independent syntheses of 3 by the groups of Danishefsky, Overman, and Williams.
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42
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