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DOI: 10.1055/s-0031-1290695
Ansamitocin Libraries by Combining Mutasynthesis with Chemical Synthesis; A New Version of Total Synthesis
Publication History
Received: 03 December 2011
Accepted after revision: 24 January 2012
Publication Date:
24 May 2012 (online)
Abstract
Blocked mutants of Actinosynnema pretiosum, the producer of the highly cytotoxic antitumor agent ansamitocin, serve as powerful tools that allow synthetic chemists to generate natural product libraries. The power of this approach can be dramatically expanded when mutasynthesis is combined with chemical synthesis. This report provides illustrative examples of the application of this strategy to produce libraries based on the ansamycin antibiotics.
1 Introduction
2 Mutasynthesis — A Powerful Strategy for Accessing New Ansamitocin Derivatives
3 Mutasynthesis Combined with Semisynthesis; Further Generalization of a Diversity Concept
4 Mutasynthesis with Advanced Synthetic Intermediates
5 Blocked Mutants as Tools for Biosynthetic Studies of Ansamitocins
6 Conclusions
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References
- 1 Kupchan SM, Komoda Y, Court WA, Thomas GJ, Smith RM, Karim A, Gilmore CJ, Haltiwanger RC, Bryan RF. J. Am. Chem. Soc. 1972; 94: 1354
- 2 Higashide E, Asai M, Ootsu K, Tanida S, Kozai Y, Hasegawa T, Kishi T, Sugino Y, Yoneda M. Nature 1977; 270: 721
-
For reviews, see:
- 3a Floss HG, Yu T.-w, Arakawa K. J. Antibiot. 2011; 64: 35
- 3b Kirschning A, Harmrolfs K, Knobloch T. C. R. Chim. 2008; 11: 1523
- 3c Cassady JM, Chan KK, Floss HG, Leistner E. Chem. Pharm. Bull. 2004; 52: 1
- 3d Komoda Y, Kishi T. Anticancer Agents Based on Natural Product Models . Douros J, Cassady JM. Academic Press; New York: 1980: 353-389
- 4 Annual Report to the FDA by DCT, NCI, on Maytansine, NSC 153858, IND 11857, February 1984
-
Disulfide-linked antibody–maytansinoid conjugates were reported by Chari and co-workers, see:
- 5a Chari RV. J, Martell BA, Gross JL, Cook SB, Shah SA, Blättler WA, McKenzie SJ, Goldmacher VS. Cancer Res. 1992; 52: 127
- 5b Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y, Goldmacher VS, Xie H, Steeves RM, Lutz RJ, Zhao R, Wang L, Blättler WA, Chari RV. J. J. Med. Chem. 2006; 49: 4392
- 5c Erickson HK, Park PU, Widdison WC, Kovtun YV, Garrett LM, Hoffman K, Lutz RJ, Goldmacher VS, Blättler WA. Cancer Res. 2006; 66: 4426
- 5d Ladino CA, Chari RV. J, Bourret LA, Kedersha NL, Goldmacher VS. Int. J. Cancer 1997; 73: 859
- 6a Lambert JM. Curr. Opin. Pharmacol. 2005; 5: 543
- 6b Kratz F, Ajaj KA, Warnecke A. Expert Opin. Invest. Drugs 2007; 16: 1037
- 8 Low PS, Henne WA, Doorneweerd DD. Acc. Chem. Res. 2008; 41: 120
- 9a Arap W, Pasqualini R, Ruoslahti E. Science 1998; 279: 377
- 9b Janssen ML, Oyen WJ, Dijkgraaf I, Massuger LF, Frielink C, Edwards DS, Rajopadhye M, Boonstra H, Corstens FH, Boerman OC. Cancer Res. 2002; 62: 6146
- 9c Haubner R, Wester HJ, Burkhart F, Senekowitsch-Schmidtke R, Weber W, Goodman SL, Kessler H, Schwaiger M. Bioconjugate Chem. 2001; 12: 84
- 10a Niculescu-Duvaz I. Curr. Opin. Mol. Ther. 2010; 12: 350
- 10b Junutula JR, Flagella KM, Graham RA, Parsons KL, Ha E, Raab H, Bhakta S, Nguyen T, Dugger DL, Li G, Mai E, Phillips GD, Hiraragi H, Fuji RN, Tibbitts J, Vandlen R, Spencer SD, Scheller RH, Polakis P, Sliwkowski MX. Clin. Cancer Res. 2010; 16: 4769
- 11 Asai M, Mizuta E, Izawa M, Haibara K, Kishi T. Tetrahedron 1979; 35: 1079
- 12 Kawai A, Akimoto H, Kozai Y, Ootsu K, Tanida S, Hashimoto N, Nomura H. Chem. Pharm. Bull. 1984; 32: 3441
- 13 Widdison WC, Chari RV. J. US. Patent 20,070,112,188, 2007
- 14 Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y, Goldmacher VS, Xie H, Stevens RM, Lutz RJ, Zhao R, Wang L, Blättler WA, Chari RV. J. J. Med. Chem. 2006; 49: 4392
- 15 Miyashira O, Akimoto H. US. Patent 4,256,746, 1981
- 16 Kawai A, Akimoto H, Hashimoto N, Nomura H. Chem. Pharm. Bull. 1984; 32: 2194
- 17a Nakahama K, Izawa M, Asai M, Kida M, Kishi T. J. Antibiot. 1981; 34: 1581
- 17b Izawa M, Nakahama K, Kasahara F, Asai M, Kishi T. J. Antibiot. 1981; 34: 1587
- 17c Izawa M, Wada Y, Kasahara F, Asai M, Kishi T. J. Antibiot. 1981; 34: 1591
- 18a Tanida S, Izawa M, Hasegawa T. J. Antibiot. 1981; 34: 489
- 18b Izawa M, Tanida S, Asai M. J. Antibiot. 1981; 34: 496
- 19 Meyers AI, Reider PJ, Campell AL. J. Am. Chem. Soc. 1980; 102: 6597 ; and references cited therein
- 20 Corey EJ, Weigel LO, Chamberlin AR, Cho H, Hua DH. J. Am. Chem. Soc. 1980; 102: 6615 ; and references cited therein
- 21 Isobe M, Kitamura M, Goto T. J. Am. Chem. Soc. 1982; 104: 4997 ; and references cited therein
- 22 Benechie M, Khuong-Huu F. J. Org. Chem. 1996; 61: 7133 ; and references cited therein
-
For reviews, see:
- 23a Weist S, Süssmuth RD. Appl. Microbiol. Biotechnol. 2005; 68: 141
- 23b Kirschning A, Taft F, Knobloch T. Org. Biomol. Chem. 2007; 3245
- 24a Rinehart KL. Jr. Pure Appl. Chem. 1977; 49: 1361
- 24b Rinehart KL. Jr. Jpn. J. Antibiot. 1979; 32: suppl. S32-46
- 25a Gregory MA, Petkovic H, Lill RE, Moss SJ, Wilkinson B, Gaisser S, Leadlay PL, Sheridan RM. Angew. Chem. Int. Ed. 2005; 44: 4757 ; Angew. Chem. 2005, 117, 4835
- 25b Ziehl M, He J, Dahse H.-M, Hertweck C. Angew. Chem. Int. Ed. 2005; 44: 1202 ; Angew. Chem. 2005, 117, 1226
- 26 Spiteller P, Bai L, Shang G, Carroll BJ, Yu T.-W, Floss HG. J. Am. Chem. Soc. 2003; 125: 14236
- 27 Yu T.-W, Bai L, Clade D, Hoffmann D, Toelzer S, Trinh KQ, Xu J, Moss SJ, Leistner E, Floss HG. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 7968
- 28 Taft F, Brünjes M, Floss HG, Czempinski N, Grond S, Sasse F, Kirschning A. ChemBioChem 2008; 9: 1057
- 29 Meyer A, Brünjes M, Taft F, Frenzel T, Sasse F, Kirschning A. Org. Lett. 2007; 9: 1489
- 30 Knobloch T, Harmrolfs K, Taft F, Thomaszewski B, Sasse F, Kirschning A. ChemBioChem 2011; 12: 540
-
N-Glucosylated ansamitocin derivatives have been reported as byproducts during solid agar fermentations before, see:
- 31a Ma J, Zhao P.-J, Shen Y.-M. Arch. Pharmacal. Res. 2007; 30: 670
- 31b Lu C, Bai L, Shen Y. J. Antibiot. 2004; 57: 348
- 31c Snipes CE, Duebelbeis DO, Olson M, Hahn DR, Dent WH. III, Gilbert JR, Werk TL, Davis GE, Lee-Lu R, Graupner PR. J. Nat. Prod. 2007; 70: 1578
- 32 Taft F., Harmrolfs K., Nickeleit I., Heutling A., Kiene M., Malek N., Sasse F., Kirschning A. Chem. Eur. J. 2012, 18, 860
- 33 Eichner S., Knobloch T., Floss H. G., Fohrer J., Harmrolfs K., Hermane J., Schulz A., Sasse F., Spiteller P., Taft F., Kirschning A. Angew. Chem. Int. Ed. 2012, 51, 752; Angew. Chem. 2012, 124, 776
- 34a Kim C.-G, Yu TW, Fryhle CB, Handa S, Floss HG. J. Biol. Chem. 1998; 273: 6030
- 34b Arakawa K, Müller R, Mahmud T, Yu T.-W, Floss HG. J. Am. Chem. Soc. 2002; 124: 10644
- 35 Pompeo F, Mushtaq A, Sim E. Protein Expression Purif. 2002; 24: 138
- 36a August PR, Tang L, Yoon YJ, Ning S, Müller R, Yu TW, Taylor M, Hoffmann D, Kim CG, Zhang X, Hutchinson CR, Floss HG. Chem. Biol. 1998; 5: 69
- 36b Rascher A, Hu Z, Viswanathan N, Schirmer A, Reid R, Nierman WC, Lewis M, Hutchinson CR. FEMS Microbiol. Lett. 2003; 218: 223
- 37 Chemically, amide synthases perform analogous transformations to the thioesterases responsible for macrolactonization and macrolactamization of polyketides and nonribosomal peptides (NRP)
- 38 Harmrolfs K, Brünjes M, Dräger G, Floss HG, Sasse F, Taft F, Kirschning A. ChemBioChem 2010; 11: 2517
- 39 Fenzel T, Brünjes M, Quitschalle M, Kirschning A. Org. Lett. 2006; 8: 135
- 40 Kubota T, Brünjes M, Frenzel T, Xu J, Kirschning A, Floss HG. ChemBioChem 2006; 7: 1221
- 41 Taft F, Brünjes M, Knobloch T, Floss HG, Kirschning A. J. Am. Chem. Soc. 2009; 131: 3812
- 42 Trost BM, McEachern EJ, Toste FD. J. Am. Chem. Soc. 1998; 120: 12702