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Kahalalide f and related compoundsKahalalide f and related compounds description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20080318849, Kahalalide f and related compounds. Brief Patent Description - Full Patent Description - Patent Application Claims
KAHALALIDE F AND RELATED COMPOUNDS
This application claims priority as a continuation under 35 U.S.C. 120 from U.S. Ser. No. 10/182,881, filed Jun. 3, 2003, as entry of the national phase of PCT/GB01/000576, filed Feb. 9, 2001, claiming priority under 35 U.S.C. 119(a)-(d) from UK 0002952, filed Feb. 9, 2000. The contents of each of the above-listed applications are incorporated by reference. The present invention relates to kahalalide compounds, and in particular to kahalalide F and related compounds, as well as a synthetic route for such compounds. BACKGROUND OF THE INVENTIONKahalalide F is a bioactive cyclic depsipeptide isolated from the sarcoglossan mollusc Elysia rufescens and its diet, the green alga Bryopsis sp. Kahalalide F was first isolated by Hamann and Scheuer, see Hamann, M. T.; Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 5825-5826. In this publication, the absolute stereochemistry of individual valines (3 D-Val and 2 L-Val) and of threonines (L-Thr and D-allo-Thr) was not determined. In a later publication, Scheuer et al. (Goetz, G.; Yoshida, W. Y.; Scheuer, P. J. Tetrahedron 1999, 55, 7739-7746) assigned a position in the molecule for the 5 Val and the 2 Thr. Thus, the structure for Kahalalide F according to Scheuer et al. was:
In the meantime, Prof. Reinhart also assigned the individual position of the 5-Val and the 2-Thr (K. L. Rinehart, personal communication). While for the 2 Thr and 3 Val, his assignation concords with that of Prof. Scheuer, for the last 2 Val there is a discrepancy. Thus, in the Rinehart assignment, the two consecutive Val in the side chain are switched and the structure is of the formula (I):
It is now accepted, and demonstrated again in this text, that the correct formula for kahalalide F is the formula (I). The structure is complex, comprising six amino acids as a cyclic part, and an exocyclic chain of seven amino acids with a terminal acyl group. Kahalalide F (I) is an exceedingly potent and rare marine-derived antitumour agent, though the absence of adequate quantities has slowed plans for clinical trials. Other kahalalide compounds are known, and for example we refer to Hamann, M. T., et al., J. Org. Chem., 1996, “Kahalalides: Bioactive Peptides from Marine Mollusk Elysia rufescens and its Algal Diet Bryopsis sp.”, vol. 61, pp. 6594-6660. As well as kahalalide F, this article gives structures for kahalalides A to E. Kahalalide K was reported in J Nat. Prod. 1999, 62, 1169, and kahalalide O was reported in J Nat Prod 2000, 63, 152. The structures for these further kahalalide compounds are shown in the following formulae:
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