Case Studies of the Synthesis of Bioactive Cyclodepsipeptide Natural Products

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2013 Jan 26

PMID 23348990

Citations 5

Authors

Sara C Stolze

Markus Kaiser

Affiliations

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Abstract

Cyclodepsipeptide natural products often display intriguing biological activities that along with their complex molecular scaffolds, makes them interesting targets for chemical synthesis. Although cyclodepsipeptides feature highly diverse chemical structures, their synthesis is often associated with similar synthetic challenges such as the establishment of a suitable macrocyclization methodology. This review therefore compiles case studies of synthetic approaches to different bioactive cyclodepsipeptide natural products, thereby illustrating obstacles of cyclodepsipeptide synthesis as well as their overcomings.

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References

von Elert E, Oberer L, Merkel P, Huhn T, Blom J . Cyanopeptolin 954, a chlorine-containing chymotrypsin inhibitor of Microcystis aeruginosa NIVA Cya 43. J Nat Prod. 2005; 68(9):1324-7. DOI: 10.1021/np050079r. View

Bowers A, West N, Taunton J, Schreiber S, Bradner J, Williams R . Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor. J Am Chem Soc. 2008; 130(33):11219-22. PMC: 3090445. DOI: 10.1021/ja8033763. View

Jiang W, Wanner J, Lee R, Bounaud P, Boger D . Total synthesis of the ramoplanin A2 and ramoplanose aglycon. J Am Chem Soc. 2002; 124(19):5288-90. DOI: 10.1021/ja020237q. View

Nielsen T, Le Quement S, Meldal M . Solid-phase synthesis of carboxylic and oxamic acids via OsO4/NaIO4/HMTA-mediated oxidative cleavage of acetylenic peptides. Org Lett. 2007; 9(13):2469-72. DOI: 10.1021/ol070693p. View

Robertson B, Wengryniuk S, Coltart D . Asymmetric total synthesis of apratoxin D. Org Lett. 2012; 14(20):5192-5. DOI: 10.1021/ol302309c. View

Vera M, Joullie M . Natural products as probes of cell biology: 20 years of didemnin research. Med Res Rev. 2002; 22(2):102-45. DOI: 10.1002/med.10003. View

Eggen M, Georg G . The cryptophycins: their synthesis and anticancer activity. Med Res Rev. 2002; 22(2):85-101. DOI: 10.1002/med.10002. View

Boger D, Lee R, Bounaud P, Meier P . Asymmetric synthesis of orthogonally protected L-threo-beta-hydroxyasparagine. J Org Chem. 2000; 65(20):6770-2. DOI: 10.1021/jo000628s. View

Takizawa T, Watanabe K, Narita K, Oguchi T, Abe H, Katoh T . Total synthesis of spiruchostatin B, a potent histone deacetylase inhibitor, from a microorganism. Chem Commun (Camb). 2008; (14):1677-9. DOI: 10.1039/b718310k. View

10.

Ma D, Zou B, Cai G, Hu X, Liu J . Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities. Chemistry. 2006; 12(29):7615-26. DOI: 10.1002/chem.200600599. View

11.

Blom J, Bister B, Bischoff D, Nicholson G, Jung G, Sussmuth R . Oscillapeptin J, a new grazer toxin of the freshwater cyanobacterium Planktothrix rubescens. J Nat Prod. 2003; 66(3):431-4. DOI: 10.1021/np020397f. View

12.

Sarabia F, Chammaa S, Sanchez Ruiz A, Ortiz L, Herrera F . Chemistry and biology of cyclic depsipeptides of medicinal and biological interest. Curr Med Chem. 2004; 11(10):1309-32. DOI: 10.2174/0929867043365224. View

13.

Narita K, Kikuchi T, Watanabe K, Takizawa T, Oguchi T, Kudo K . Total synthesis of the bicyclic depsipeptide HDAC inhibitors spiruchostatins A and B, 5''-epi-spiruchostatin B, FK228 (FR901228) and preliminary evaluation of their biological activity. Chemistry. 2009; 15(42):11174-86. DOI: 10.1002/chem.200901552. View

14.

Jiang W, Wanner J, Lee R, Bounaud P, Boger D . Total synthesis of the ramoplanin A2 and ramoplanose aglycon. J Am Chem Soc. 2003; 125(7):1877-87. DOI: 10.1021/ja0212314. View

15.

Chen Y, Gambs C, Abe Y, Wentworth Jr P, Janda K . Total synthesis of the depsipeptide FR-901375. J Org Chem. 2003; 68(23):8902-5. DOI: 10.1021/jo034765b. View

16.

Fuse S, Okada K, Iijima Y, Munakata A, Machida K, Takahashi T . Total synthesis of spiruchostatin B aided by an automated synthesizer. Org Biomol Chem. 2011; 9(10):3825-33. DOI: 10.1039/c0ob01169j. View

17.

Taori K, Paul V, Luesch H . Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp. J Am Chem Soc. 2008; 130(6):1806-7. DOI: 10.1021/ja7110064. View

18.

Di Maro S, Pong R, Hsieh J, Ahn J . Efficient solid-phase synthesis of FK228 analogues as potent antitumoral agents. J Med Chem. 2008; 51(21):6639-41. DOI: 10.1021/jm800959f. View

19.

Shigematsu N, Ueda H, Takase S, Tanaka H, Yamamoto K, Tada T . FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. II. Structure determination. J Antibiot (Tokyo). 1994; 47(3):311-4. DOI: 10.7164/antibiotics.47.311. View

20.

Jimenez J, Royo M, Giralt E, Albericio F . Synthesis and structure determination of kahalalide F (1,2). J Am Chem Soc. 2001; 123(46):11398-401. DOI: 10.1021/ja0116728. View