Trunkamide

Carroll, A.R. Coll, J.C. Bourne, D.J. Macleod, J.K. Zabriskie, T.M. Ireland, C.M. Bowden, B.F. (1996) Patellins 1-6 and trunkamide A novel cyclic hexa-, hepta- and octa-peptides from colonial ascidians, Lissoclinum sp. Aust. J. Chem., 49, 659-67. 

Wipf, P. Yoshikazu, U. (2000A) Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A. J. Org. Chem., 65, 1037-49. 

L. patella from Fiji contained patellins 1-5 (50-54) [82] and earlier, solution- and solid-state conformational studies were carried out on patellin 2 (51), and the structure was determined by X-ray analysis [83]. A Lissoclinum sp. from the Great Barrier Reef yielded patellins 3 (52), 5 (54) and 6 (55) and the heptapeptide trunkamide A (56) [82]. Compounds 50-56 were all identified by interpretation of spectral data and through use of Marfey s method to determine the absolute stereochemistry of the constituent amino acids [82]. A total synthesis of the proposed structure of trunkamide A (56) revealed that the structure... 

Solution- and solid-state conformations of tawicyclamides A (57) and B (58), proline-containing cyclic peptides from a Philippines specimen of L. patella, were determined by spectroscopic and X-ray analyses respectively [87]. Patellins 1-6 (50-55), trunkamide A (56) and the tawicyclamides A-B (57-58) all lack the oxazoline ring present in most other cyclic peptides isolated from the Lissoclinum genus [22]. 

The patellins 1-6 (382-387) and trunkamide A (388) [298, 299] along with tawicyclamides A (389) and B (390) [300] represent another variation of the cyclic peptides produced by Lissoclinum species. All of these compounds lack the characteristic oxazoline ring present in most Lissoclinum cyclic peptides. Compounds 382-386 and 388 were inactive in a series of in vitro cytotoxicity assays while 387, 389, and 390 showed modest cytotoxicity, supporting the importance of the presence of the oxazoline ring for cytotoxic activity [298, 300],... 

During this time, the total synthesis of several marine sulfur-containing natural products cited in this review has been reported and they confirmed the suggested structures. This is the case of the synthesis of some sulfonoceramides (e.g. flavocristamide A (318) discussed in the sulfonic acid and their derivatives section [366], and the synthesis of the thiazole-containing compounds bistratamide D (381) [367], trunkamide (388) [368], mollamide (393) [369], dolastatin I (409) [370], and virenamide B (414) [371]. 

A prenylated cyclopeptide trunkamide A 391 produced by ascidians of the genus Lissoclinum, and also its C45 epimer, were isolated <2001TL2573, 2003T2713>. 

Metagenomic approaches have been used to study metabolites produced by bacterial symbionts of marine animals, insects, and nematodes. The literature now provides several examples where DNA-based strategies targeting specific genetic loci have enabled the isolation and cloning of biosynthetic gene clusters encoding for the biosynthesis of important symbiont-associated molecules such as pederin, onn amide A, bryostatins, trunkamide, theopalauamide, and the patellamides. These studies are the focus of another chapter in this series and therefore will not be discussed here. 

Figure 4 Cyanobactin gene ciusters. (a) Trichamide ciuster. (b) Pateiiamide gene ciuster. Syntenic gene ciusters were identified for tenuecyciamides and microcyciamides. (c) Trunkamide gene ciuster ieading to prenyiation.

Lissoclinum sp. Patellins 1-6, Trunkamide A Carroll et al., 1996b Wipf and Uto, 2000... 

Patellins 1-6 and trunkamide A, isolated from an undetermined species of Lissodinum harvested on the Great Barrier Reef (Trunk island), are all reverse prenyl substituted cyclopeptides and contain only thiazolines as... 

Wipf P. and Uto, Y. (1999) Total synthesis of the putative structure of the marine matabolite trunkamide A. Tetrahedron Lett., 40, 5165-5169. 

McKeever, B. and Pattenden, G. (2001) Total synthesis of the prenylated cyclopeptide trunkamide A, a cytotoxic metabolite from Lissodinum sp. Tetrahedron Lett., 42, 2573-2577. 

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