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Journal articles on the topic 'Mycalamide'

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Author: Grafiati

Published: 10 December 2022

Last updated: 30 January 2023

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1

Gürel, Güliz, Gregor Blaha, Thomas A. Steitz, and Peter B. Moore. "Structures of Triacetyloleandomycin and Mycalamide A Bind to the Large Ribosomal Subunit of Haloarcula marismortui." Antimicrobial Agents and Chemotherapy 53, no. 12 (September 8, 2009): 5010–14. http://dx.doi.org/10.1128/aac.00817-09.

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ABSTRACT Structures have been obtained for the complexes that triacetyloleandomycin and mycalamide A form with the large ribosomal subunit of Haloarcula marismortui. Triacetyloleandomycin binds in the nascent peptide tunnel and inhibits the activity of ribosomes by blocking the growth of the nascent peptide chain. Mycalamide A binds to the E site and inhibits protein synthesis by occupying the space normally occupied by the CCA end of E-site-bound tRNAs.

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2

Roush, William R., and Lance A. Pfeifer. "Total Synthesis of Mycalamide A and 7-epi-Mycalamide A." Organic Letters 2, no. 6 (March 2000): 859–62. http://dx.doi.org/10.1021/ol005629l.

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3

Nakata, Tadashi, Shunya Takahashi, and Akihiro Okada. "Synthesis of Mycalamide Analogs." HETEROCYCLES 63, no. 9 (2004): 2111. http://dx.doi.org/10.3987/com-04-10162.

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4

Toyota, M., N. Kagawa, and M. Ihara. "Synthesis of (+)-Mycalamide A." Synfacts 2006, no. 8 (August 2006): 0750. http://dx.doi.org/10.1055/s-2006-941928.

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5

Kocienski, Philip J., Robert Narquizian, Piotr Raubo, Christopher Smith, and F. Thomas Boyle. "A Synthesis of Mycalamide B." Synlett 1998, no. 8 (August 1998): 869–72. http://dx.doi.org/10.1055/s-1998-1803.

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6

Sohn, Jeong-Hun, Nobuaki Waizumi, H. Marlon Zhong, and Viresh H. Rawal. "Total Synthesis of Mycalamide A." Journal of the American Chemical Society 127, no. 20 (May 2005): 7290–91. http://dx.doi.org/10.1021/ja050728l.

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7

Kagawa, Natsuko, Masataka Ihara, and Masahiro Toyota. "Total Synthesis of (+)-Mycalamide A." Organic Letters 8, no. 5 (March 2006): 875–78. http://dx.doi.org/10.1021/ol052943c.

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8

Roush, William R., and Lance A. Pfeifer. "ChemInform Abstract: Total Synthesis of Mycalamide A (IX) and 7-epi-Mycalamide A (V)." ChemInform 31, no. 27 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200027232.

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9

Trost, Barry M., Hanbiao Yang, and Gary D. Probst. "A Formal Synthesis of (−)-Mycalamide A." Journal of the American Chemical Society 126, no. 1 (January 2004): 48–49. http://dx.doi.org/10.1021/ja038787r.

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10

Kagawa, Natsuko, Masataka Ihara, and Masahiro Toyota. "Convergent Total Synthesis of (+)-Mycalamide A." Journal of Organic Chemistry 71, no. 18 (September 2006): 6796–805. http://dx.doi.org/10.1021/jo060803q.

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11

KOCIENSKI, P. J., R. NARQUIZIAN, P. RAUBO, C. SMITH, and F. T. BOYLE. "ChemInform Abstract: A Synthesis of Mycalamide B." ChemInform 29, no. 47 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199847279.

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12

FUKUI, H., H. MATSUKURA, and T. NAKATA. "ChemInform Abstract: Total Synthesis of Mycalamide A." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807293.

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13

Kocienski, Philip, Piotr Raubo, Justin K. Davis, F. Thomas Boyle, Donna E. Davies, and Audrey Richter. "A synthesis of 18-O-methyl mycalamide B." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (1996): 1797. http://dx.doi.org/10.1039/p19960001797.

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14

Hoffmann, Reinhard W., and Achim Schlapbach. "Synthesis of the trioxadecalin-part of mycalamide B." Tetrahedron Letters 34, no. 49 (December 1993): 7903–6. http://dx.doi.org/10.1016/s0040-4039(00)61506-x.

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15

Kocienski, Philip J. "A Formal Synthesis of 18-O-Methyl Mycalamide B." Synthesis 1999, no. 12 (December 1999): 2087–95. http://dx.doi.org/10.1055/s-1999-3633.

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16

Nakata, Tadashi, Shunya Takahashi, Akihiro Okada, and Miho Nishiwaki. "Synthesis and Biological Activities of Sugar Analogs of Mycalamide A." HETEROCYCLES 69, no. 1 (2006): 487. http://dx.doi.org/10.3987/com-06-s(o)35.

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17

Fukui, Hideto, Yoshinori Tsuchiya, Keiko Fujita, Tadakiyo Nakagawa, Hiroyuki Koshino, and Tadashi Nakata. "Synthesis and biological activity of artificial analogs of mycalamide A." Bioorganic & Medicinal Chemistry Letters 7, no. 16 (August 1997): 2081–86. http://dx.doi.org/10.1016/s0960-894x(97)00365-x.

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18

HOFFMANN, R. W., and A. SCHLAPBACH. "ChemInform Abstract: Synthesis of the Trioxadecalin Part of Mycalamide B." ChemInform 25, no. 14 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199414299.

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19

KOCIENSKI, P., P. RAUBO, J. K. DAVIS, F. T. BOYLE, D. E. DAVIES, and A. RICHTER. "ChemInform Abstract: A Synthesis of 18-O-Methyl Mycalamide B." ChemInform 28, no. 10 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199710186.

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20

Thompson, Andrew M., John W. Blunt, Murray H. G. Munro, and Bruce M. Clark. "Chemistry of the mycalamides, antiviral and antitumour compounds from a marine sponge. Part 4. Reactions of mycalamide A and alkyl derivatives with basic nucleophiles." Journal of the Chemical Society, Perkin Transactions 1, no. 8 (1994): 1025. http://dx.doi.org/10.1039/p19940001025.

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21

Nakata, Tadashi, Hideto Fukui, Tadakiyo Nakagawa, and Hiroko Matsukura. "Total Synthesis of Mycalamide A. Further Synthetic Study of the Right Half." HETEROCYCLES 42, no. 1 (1996): 159. http://dx.doi.org/10.3987/com-95-s64.

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22

Dang, Y., T. Schneider-Poetsch, D. E. Eyler, J. C. Jewett, S. Bhat, V. H. Rawal, R. Green, and J. O. Liu. "Inhibition of eukaryotic translation elongation by the antitumor natural product Mycalamide B." RNA 17, no. 8 (June 21, 2011): 1578–88. http://dx.doi.org/10.1261/rna.2624511.

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23

Nakata, Tadashi, Hiroko Matsukura, Dunlong Jian, and Hiroaki Nagashima. "Synthesis of the right half of mycalamide A. A formal total synthesis." Tetrahedron Letters 35, no. 44 (October 1994): 8229–32. http://dx.doi.org/10.1016/0040-4039(94)88289-4.

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24

West, Lyndon M., Peter T. Northcote, Kylie A. Hood, John H. Miller, and Michael J. Page. "Mycalamide D, a New Cytotoxic Amide from the New Zealand Marine SpongeMycaleSpecies." Journal of Natural Products 63, no. 5 (May 2000): 707–9. http://dx.doi.org/10.1021/np9904511.

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25

FUKUI, H., Y. TSUCHIYA, K. FUJITA, T. NAKAGAWA, H. KOSHINO, and T. NAKATA. "ChemInform Abstract: Synthesis and Biological Activity of Artificial Analogues of Mycalamide A." ChemInform 28, no. 51 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199751279.

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26

Marron, Thomas G., and William R. Roush. "Diastereoselective synthesis of N-benzoyl mycalamine, the fully elaborated trioxadecalin nucleus of mycalamide. A. Control of the key N-acyl aminal stereocenter via carbamate acylation." Tetrahedron Letters 36, no. 10 (March 1995): 1581–84. http://dx.doi.org/10.1016/0040-4039(95)00093-r.

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27

THOMPSON, A. M., J. W. BLUNT, M. H. G. MUNRO, and B. M. CLARK. "ChemInform Abstract: Chemistry of the Mycalamides, Antiviral and Antitumour Compounds from a Marine Sponge. Part 4. Reactions of Mycalamide A and Alkyl Derivatives with Basic Nucleophiles." ChemInform 25, no. 33 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199433295.

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28

Ihara, Masataka, Marcellino Rudyanto, Masahiro Toyota, and Natsuko Kagawa. "A Concise Synthesis of a Potential Key Intermediate for 12-epi- Mycalamide A." HETEROCYCLES 58, no. 1 (2002): 655. http://dx.doi.org/10.3987/com-02-s(m)55.

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29

MARRON, T. G., and W. R. ROUSH. "ChemInform Abstract: Diastereoselective Synthesis of N-Benzoyl Mycalamine, the Fully Elaborated Trioxadecalin Nucleus of Mycalamide A. Control of the Key N- Acyl Aminal Stereocenter via Carbamate Acylation." ChemInform 26, no. 38 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199538303.

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30

Perry, Nigel B., John W. Blunt, Murray H. G. Munro, and Lewis K. Pannell. "Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale." Journal of the American Chemical Society 110, no. 14 (July 1988): 4850–51. http://dx.doi.org/10.1021/ja00222a067.

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31

NAKATA, T., H. FUKUI, T. NAKAGAWA, and H. MATSUKURA. "ChemInform Abstract: Total Synthesis of Mycalamide A. Further Synthetic Study of the Right Half." ChemInform 27, no. 17 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199617241.

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32

NAKATA, T., H. MATSUKURA, D. JIAN, and H. NAGASHIMA. "ChemInform Abstract: Synthesis of the Right Half of Mycalamide A. A Formal Total Synthesis." ChemInform 26, no. 14 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199514250.

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33

Mosey, R. Adam, and Paul E. Floreancig. "Isolation, biological activity, synthesis, and medicinal chemistry of the pederin/mycalamide family of natural products." Natural Product Reports 29, no. 9 (2012): 980. http://dx.doi.org/10.1039/c2np20052j.

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34

Jewett, John C., and Viresh H. Rawal. "Temporary Restraints To Overcome Steric Obstacles: An Efficient Strategy for the Synthesis of Mycalamide B." Angewandte Chemie International Edition 49, no. 46 (October 7, 2010): 8682–85. http://dx.doi.org/10.1002/anie.201003361.

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35

Jewett, John C., and Viresh H. Rawal. "Temporary Restraints To Overcome Steric Obstacles: An Efficient Strategy for the Synthesis of Mycalamide B." Angewandte Chemie 122, no. 46 (October 7, 2010): 8864–67. http://dx.doi.org/10.1002/ange.201003361.

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36

Dyshlovoy, Sergey A., Sergey N. Fedorov, Anatoly I. Kalinovsky, Larisa K. Shubina, Carsten Bokemeyer, Valentin A. Stonik, and Friedemann Honecker. "Mycalamide A Shows Cytotoxic Properties and Prevents EGF-Induced Neoplastic Transformation through Inhibition of Nuclear Factors." Marine Drugs 10, no. 12 (May 30, 2012): 1212–24. http://dx.doi.org/10.3390/md10061212.

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37

Jiang, Xin, Noelle Williams, and Jef K. De Brabander. "Synthesis of Psymberin Analogues: Probing a Functional Correlation with the Pederin/Mycalamide Family of Natural Products." Organic Letters 9, no. 2 (January 2007): 227–30. http://dx.doi.org/10.1021/ol062656o.

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38

Rust, Michael, Eric J. N. Helfrich, Michael F. Freeman, Pakjira Nanudorn, Christopher M. Field, Christian Rückert, Tomas Kündig, et al. "A multiproducer microbiome generates chemical diversity in the marine sponge Mycale hentscheli." Proceedings of the National Academy of Sciences 117, no. 17 (April 14, 2020): 9508–18. http://dx.doi.org/10.1073/pnas.1919245117.

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Bacterial specialized metabolites are increasingly recognized as important factors in animal–microbiome interactions: for example, by providing the host with chemical defenses. Even in chemically rich animals, such compounds have been found to originate from individual members of more diverse microbiomes. Here, we identified a remarkable case of a moderately complex microbiome in the sponge host Mycale hentscheli in which multiple symbionts jointly generate chemical diversity. In addition to bacterial pathways for three distinct polyketide families comprising microtubule-inhibiting peloruside drug candidates, mycalamide-type contact poisons, and the eukaryotic translation-inhibiting pateamines, we identified extensive biosynthetic potential distributed among a broad phylogenetic range of bacteria. Biochemical data on one of the orphan pathways suggest a previously unknown member of the rare polytheonamide-type cytotoxin family as its product. Other than supporting a scenario of cooperative symbiosis based on bacterial metabolites, the data provide a rationale for the chemical variability of M. hentscheli and could pave the way toward biotechnological peloruside production. Most bacterial lineages in the compositionally unusual sponge microbiome were not known to synthesize bioactive metabolites, supporting the concept that microbial dark matter harbors diverse producer taxa with as yet unrecognized drug discovery potential.

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39

Kocienski, Philip, Robert Narquizian, Piotr Raubo, Christopher Smith, Louis J. Farrugia, Kenneth Muir, and F. Thomas Boyle. "Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (2000): 2357–84. http://dx.doi.org/10.1039/a909898d.

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40

Jewett, John C., and Viresh H. Rawal. "ChemInform Abstract: Temporary Restraints to Overcome Steric Obstacles: An Efficient Strategy for the Synthesis of Mycalamide B." ChemInform 42, no. 10 (February 10, 2011): no. http://dx.doi.org/10.1002/chin.201110214.

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41

DAVIS, J., P. J. KOCIENSKI, and T. BOYLE. "ChemInform Abstract: An Approach to the Synthesis of Mycalamide B. Construction of the 2,4, 7-Trioxabicyclo(4.4.0)decane Ring System (XV)." ChemInform 26, no. 16 (April 18, 1995): no. http://dx.doi.org/10.1002/chin.199516301.

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42

Kocienski, Philip, Robert Narquizian, Piotr Raubo, Christopher Smith, Louis J. Farrugia, Kenneth Muir, and F. Thomas Boyle. "ChemInform Abstract: Synthetic Studies on the Pederin Family of Antitumor Agents. Syntheses of Mycalamide B (XIII), Theopederin D (XVI) and Pederin (XVIII)." ChemInform 31, no. 48 (November 28, 2000): no. http://dx.doi.org/10.1002/chin.200048240.

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43

Galvin, Frances, Gordon J. Freeman, Ziba Razi-Wolf, Baruj Benacerraf, Lee Nadler, and Hans Reiser. "Effects of cyclosporin A, FK 506, and mycalamide A on the activation of murine CD4+ T cells by the murine B7 antigen." European Journal of Immunology 23, no. 1 (January 1993): 283–86. http://dx.doi.org/10.1002/eji.1830230145.

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44

Hong, Chang Yong, and Yoshito Kishi. "Total synthesis of mycalamides A and B." Journal of Organic Chemistry 55, no. 14 (July 1990): 4242–45. http://dx.doi.org/10.1021/jo00301a007.

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45

Simpson, Jamie S., Mary J. Garson, John W. Blunt, Murray H. G. Munro, and John N. A. Hooper. "Mycalamides C and D, Cytotoxic Compounds from the Marine SpongeStylinosn. Species." Journal of Natural Products 63, no. 5 (May 2000): 704–6. http://dx.doi.org/10.1021/np990431z.

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46

Zhong, H. Marlon, Jeong-Hun Sohn, and Viresh H. Rawal. "Studies toward the Asymmetric Synthesis of the Right Part of the Mycalamides." Journal of Organic Chemistry 72, no. 2 (January 2007): 386–97. http://dx.doi.org/10.1021/jo0615145.

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47

Trotter, Nicholas S., Shunya Takahashi, and Tadashi Nakata. "Simple and Efficient Synthesis of (+)-Methyl 7-Benzoylpederate, a Key Intermediate toward the Mycalamides." Organic Letters 1, no. 6 (September 1999): 957–59. http://dx.doi.org/10.1021/ol990936g.

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48

Gardiner, John M., Richard Mills, and Thomas Fessard. "Synthesis of model ring systems related to C10–C18 analogues of the mycalamides/theopederins." Tetrahedron Letters 45, no. 6 (February 2004): 1215–17. http://dx.doi.org/10.1016/j.tetlet.2003.11.141.

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49

J. Witczak, Zbigniew, Ricky M. Rampulla, and Ajay Bommareddy. "Mycalamides, Pederin and Psymberin as Natural Carbohydrates and Potential Antitumor Agents: Past and Future Perspectives." Mini-Reviews in Medicinal Chemistry 12, no. 14 (November 1, 2012): 1520–32. http://dx.doi.org/10.2174/138955712803832744.

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50

Hoffmann, Reinhard W., Steffen Breitfelder, and Achim Schlapbach. "Model Studies Towards a Novel Fragment Coupling for the Synthesis of Mycalamides and Related Natural Products." Helvetica Chimica Acta 79, no. 2 (March 20, 1996): 346–52. http://dx.doi.org/10.1002/hlca.19960790203.

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