Syntheses of Cyclomarins – Interesting Marine Natural Products with Distinct Mode of Action towards Malaria and Tuberculosis

Alexander Kiefer; Uli Kazmaier

doi:10.1055/s-0037-1610377

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 107-121
DOI: 10.1055/s-0037-1610377

short review

Copyright with the author

Syntheses of Cyclomarins – Interesting Marine Natural Products with Distinct Mode of Action towards Malaria and Tuberculosis

Alexander Kiefer

,

Uli Kazmaier *

Abstract

All articles of this category

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The cyclomarins are cyclic heptapeptides from marine streptomycetes containing four rather unusual amino acids. Interestingly, the cyclomarins address two completely different targets: ClpC1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp₃Aase of Plasmodium falciparum. Therefore, the cyclomarins are interesting lead structures for the development of drugs targeting tuberculosis and malaria. As a result, several synthetic protocols towards the synthesis of these unusual building blocks as well as the natural products themselves have been developed, which will be discussed in this review.

1 Introduction

2 Synthesis of the Building Blocks

3 Total Synthesis of Cyclomarin C by Yao and Co-workers

4 Total Synthesis of Cyclomarin A and C by Barbie and Kazmaier

5 Conclusion

Key words

natural products - cyclopeptides - cyclomarins - total synthesis - malaria - tuberculosis

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References

References
1 Newman DJ, Cragg GM. J. Nat. Prod. 2016; 79: 629
2 Laraia L, Waldmann H. Drug Discovery Today Technol. 2017; 23: 75
3 Rossiter SE, Fletcher MH, Wuest WM. Chem. Rev. 2017; 117: 12415
4 Chellat MF, Raguž L, Riedl R. Angew. Chem. Int. Ed. 2016; 55: 6600 ; Angew. Chem. 2016, 128, 6710
5 O’Connell KM. G, Hodgkinson JT, Sore HF, Welch M, Salmond GP. C, Spring DR. Angew. Chem. Int. Ed. 2013; 52: 10706 ; Angew. Chem. 2013, 125, 10904
6 Wright GD. Nat. Prod. Rep. 2017; 34: 694
7 Butler MS, Blaskovich MA, Cooper MA. J. Antibiot. (Tokyo) 2017; 70: 3
8 Dang T, Süssmuth RD. Acc. Chem. Res. 2017; 50: 1566
9 Renner MK, Shen Y.-C, Cheng X.-C, Jensen PR, Frankmoelle W, Kauffman CA, Fenical W, Lobkovsky E, Clardy J. J. Am. Chem. Soc. 1999; 121: 11273
10 Pazoles CJ, Siegel SA. US 5759995, 1998
11 Schmitt EK, Riwanto M, Sambandamurthy V, Roggo S, Miault C, Zwingelstein C, Krastel P, Noble C, Beer D, Rao SP. S, Au M, Niyomrattanakit P, Lim V, Zheng J, Jeffery D, Pethe K, Camacho LR. Angew. Chem. Int. Ed. 2011; 50: 5889
12 Vasudevan D, Rao SP. S, Noble CG. J. Biol. Chem. 2013; 288: 30883
13 Weinhäupl K, Brennich M, Kazmaier U, Lelievre J, Ballell L, Goldberg A, Schanda P, Fraga H. J. Biol. Chem. 2018; 293: 8379
14 Bürstner N, Roggo S, Ostermann N, Blank J, Delmas C, Freuler F, Gerhartz B, Hinniger A, Hoepfner D, Liechty B, Mihalic M, Murphy J, Pistorius D, Rottmann M, Thomas JR, Schirle M, Schmitt EK. ChemBioChem 2015; 16: 2433
15 Intaraudom C, Rachtawee P, Suvannakad R, Pittayakhajonwut P. Tetrahedron 2011; 67: 7593
16 Schultz AW, Oh DC, Carney JR, Williamson RT, Udwary DW, Jensen PR, Gould SJ, Fenical W, Moore BS. J. Am. Chem. Soc. 2008; 130: 4507
17 Qian Q, Schultz AW, Moore BS, Tanner ME. Biochemistry 2012; 51: 7733
18 Schultz AW, Lewis CA, Luzung MR, Baran PS, Moore BS. J. Nat. Prod. 2010; 73: 373
19 Haruhiko T, Takehiko T, Yoshihiro T, Fumiaki H. Chem. Lett. 1992; 21: 431
20 Kikuchi M, Konno H. Org. Lett. 2014; 16: 4324
21 Oku N, Gustafson KR, Cartner LK, Wilson JA, Shigematsu N, Hess S, Pannell LK, Boyd MR, McMahon JB. J. Nat. Prod. 2004; 67: 1407
22 Ford PW, Gustafson KR, McKee TC, Shigematsu N, Maurizi LK, Pannell LK, Williams DE, Dilip de Silva E, Lassota P, Allen TM, Van Soest R, Andersen RJ, Boyd MR. J. Am. Chem. Soc. 1999; 121: 5899
23 Plaza A, Gustchina E, Baker HL, Kelly M, Bewley CA. J. Nat. Prod. 2007; 70: 1753
24 Ma J, Huang H, Xie Y, Liu Z, Zhao J, Zhang C, Jia Y, Zhang Y, Zhang H, Zhang T, Ju J. Nat. Commun. 2017; 8: 391
25 Shibata M, Yamamoto H, Nakazawa K. Agric. Biol. Chem. 1962; 26: 228
26 Higashide E, Shibata M, Yamamoto H, Nakazawa K, Iwasaki H, Ueyanagi J, Miyake A. Agric. Biol. Chem. 1962; 26: 234
27 Ueda K, Xiao J, Doket N, Nakatsuka S. Biosci. Biotechnol. Biochem. 1992; 33: 5377
28 Isogai A, Nakayama J, Takayama S, Kusai A, Suzuki A. Biosci. Biotechnol. Biochem. 1992; 56: 1079
29 Sugiyama H, Shioiri T, Yokokawa F. Tetrahedron Lett. 2002; 43: 3489
30 Wen SJ, Yao ZJ. Org. Lett. 2004; 6: 2721
31 Wen SJ, Hu TS, Yao ZJ. Tetrahedron 2005; 61: 4931
32 Barbie P, Kazmaier U. Org. Lett. 2016; 18: 204
33 Barbie P, Kazmaier U. Org. Biomol. Chem. 2016; 14: 6036
34 Barbie P, Kazmaier U. Org. Biomol. Chem. 2016; 14: 6055
35 Schöllkopf U, Groth U, Deng C. Angew. Chem., Int. Ed., Engl. 1981; 20: 798
36 Beulshausen T, Groth U, Schöllkopf U. Liebigs Ann. Chem. 1991; 1207
37 Ireland RE, Liu L, Roper TD, Gleason JL. Tetrahedron 1997; 53: 13257
38 Hajra S, Karmakar A. Tetrahedron Lett. 2004; 45: 3185
39 Hajra S, Karmakar A, Bhowmick M. Tetrahedron: Asymmetry 2006; 17: 210
40 Blaskovich MA, Lajoie GA. J. Am. Chem. Soc. 1993; 115: 5021
41 Hansen DB, Joullié MM. Tetrahedron: Asymmetry 2005; 16: 3963
42 Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T. Tetrahedron Lett. 1984; 25: 2183
43 Harmon RE, Wellman G, Gupta SK. J. Org. Chem. 1973; 38: 11
44 Evans DA, Britton TC, Ellman JA, Dorow RL. J. Am. Chem. Soc. 1990; 112: 4011
45 Evans DA, Britton TC, Ellman JA. Tetrahedron Lett. 1987; 28: 6141
46 Tarver JE, Terranova KM, Joullié MM. Tetrahedron 2004; 60: 10277
47 Davis FA, Portonovo PS, Reddy RE, Chiu Y. J. Org. Chem. 1996; 61: 440
48 Hansen DB, Starr ML, Tolstoy N, Joullié MM. Tetrahedron: Asymmetry 2005; 16: 3623
49 Nevalainen M, Koskinen AM. P. Synlett 2001; 640
50 Sathish K, Reddy GP. K, Mainkar PS, Chandrasekhar S. Tetrahedron: Asymmetry 2011; 22: 1568
51 Zwick CR, Renata H. J. Am. Chem. Soc. 2018; 140: 1165
52 Della Sala G, Izzo I, Spinella A. Synlett 2006; 1319
53 Hansen DB, Lewis AS, Gavalas SJ, Joullié MM. Tetrahedron: Asymmetry 2006; 17: 15
54 Barbie P, Kazmaier U. Org. Biomol. Chem. 2015; 13: 9267
55 Piller FM, Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P. Chem. Eur. J. 2009; 15: 7192
56 Luzung MR, Lewis CA, Baran PS. Angew. Chem. Int. Ed. 2009; 48: 7025
57 Parikh JR, Doering W. vonE. J. Am. Chem. Soc. 1967; 89: 5505
58 McDonald C, Holcomb H, Kennedy K, Kirkpatrick E, Leathers T, Vanemon P. J. Org. Chem. 1989; 54: 1213
59 McGarvey GJ, Hiner RN, Matsubara Y, Oh T. Tetrahedron Lett. 1983; 24: 2733
60 Corey EJ, Schmidt G. Tetrahedron Lett. 1979; 20: 399
61 Crich D, Banerjee A. J. Org. Chem. 2006; 71: 7106
62 Evans DA, Ripin DH. B, Halstead DP, Campos KR. J. Am. Chem. Soc. 1999; 121: 6816

63a Kazmaier U, Krebs A. Angew. Chem., Int. Ed. Engl. 1995; 34: 2012 ; Angew. Chem. 1995, 107, 2213
63b Krebs A, Kazmaier U. Tetrahedron Lett. 1996; 37: 7945
63c Mues H, Kazmaier U. Synthesis 2001; 487
63d Kazmaier U, Mues H, Krebs A. Chem. Eur. J. 2002; 8: 185

64 Mooiweer HH, Hiemstra H, Speckamp WN. Tetrahedron 1991; 47: 3451
65 Diago-Meseguer J, Palomo-Coll AL, Fernández-Lizarbe JR, Zugaza-Bilbao A. Synthesis 1980; 547
66 Coste J, Le-Nguyen D, Castro B. Tetrahedron Lett. 1990; 31: 205
67 Takahashi H, Tanahashi K, Higashiyma K, Onishi H. Chem. Pharm. Bull. 1986; 34: 479
68 Schmidt U, Griesser H, Leitenberger V, Lieberknecht A, Mangold R, Meyer R, Riedl B. Synthesis 1992; 487
69 Schmidt U, Leitenberger V, Griesser H, Schmidt J, Meyer R. Synthesis 1992; 1248
70 Van den Berg M, Minnaard AJ, Schudde EP, Van Esch J, De Vries AH. M, De Vries JG, Feringa BL. J. Am. Chem. Soc. 2000; 122: 11539
71 Panella L, Aleixandre AM, Kruidhof GJ, Robertus J, Feringa BL, De Vries JG, Minnaard AJ. J. Org. Chem. 2006; 71: 2026
72 Johnson KF, Van Zeeland R, Stanley LM. Org. Lett. 2013; 15: 2798
73 Powers JC. Tetrahedron Lett. 1965; 6: 655
74 Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
75 Kazlauskas RJ, Weissfloch AN. E, Rappaport AT, Cuccia LA. J. Org. Chem. 1991; 56: 2656

76a Kazmaier U. Amino Acids 1996; 11: 283
76b Kazmaier U. Liebigs Ann./Recl. 1997; 285
76c Kazmaier U, Schneider C. Synthesis 1998; 1321

77 Kazmaier U. Angew. Chem., Int. Ed. Engl. 1994; 33: 998
78 Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
79 Peng L, Xu JC. J. Org. Chem. 2000; 65: 2951
80 Li P. e-EROS Encycl. Reagents Org. Synth. 2003; 2
81 Shendage DM, Fröhlich R, Haufe G. Org. Lett. 2004; 6: 3675
82 Lemaire-Audoire S, Savignac M, Blart E, Pourcelot G, Genêt JP, Bernard JM. Tetrahedron Lett. 1994; 35: 8783