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Review
. 2013 May 21;11(5):1693-717.
doi: 10.3390/md11051693.

"Head-to-side-chain" cyclodepsipeptides of marine origin

Marta Pelay-Gimeno  1 , Judit Tulla-Puche, Fernando Albericio
Affiliations
Review

"Head-to-side-chain" cyclodepsipeptides of marine origin

Marta Pelay-Gimeno et al. Mar Drugs. .

Abstract

Since the late 1980s, a large number of depsipeptides that contain a new topography, referred to as "head-to-side-chain" cyclodepsipeptides, have been isolated and characterized. These peptides present a unique structural arrangement that comprises a macrocyclic region closed through an ester bond between the C-terminus and a β-hydroxyl group, and terminated with a polyketide moiety or a more simple branched aliphatic acid. This structural pattern, the presence of unique and complex residues, and relevant bioactivity are the main features shared by all the members of this new class of depsipeptides, which are reviewed herein.

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Figures

Figure 1
Figure 1
Chemical structures of (a) Ziconotide; (b) Trabectedin; and (c) Brentuximab vedotin (the box contains the moiety of marine origin), which illustrate the chemical diversity found in the sea.
Figure 2
Figure 2
Chemical structure of micropeptin EI964.
Figure 3
Figure 3
Structures of “head-to-side-chain” kahalalides plus kahalalide E. All the kahalalides displaying biological activity of interest are underlined.
Figure 4
Figure 4
Structures of natural didemnins and tamandarins.
Figure 5
Figure 5
Structures of discodermins, polydiscamides, halicylindramides, microspinosamide and corticiamide.
Figure 6
Figure 6
Chemical structures of callipeltins A and B. The stereochemistry of all chiral centers has been checked and corrected.
Figure 7
Figure 7
Chemical structures of neamphamides A–D.
Figure 8
Figure 8
Chemical structures of papuamides A–F. Stereochemical assignment of papuamide E and F has not been published to date. The stereochemistry shown is the one reported after isolation. Differences in the literature are found.
Figure 9
Figure 9
Chemical structures of theopapuamides A–D. No stereochemistry has been described for the residues diMeGln, Amtha and Htoa of theopapuamide A.
Figure 10
Figure 10
Chemical structures of mirabamides A–H.
Figure 11
Figure 11
Chemical structures of homophymines A–E and A1–E1.
Figure 12
Figure 12
Chemical structures of stellatolide A and B.
Figure 13
Figure 13
Chemical structures of pipecolidepsins A, B and C.
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