Preparation of cyclic depsipeptide compounds and a novel cyclic

Details Preparation of cyclic depsipeptide compounds and a novel cyclic Preparation of cyclic depsipeptide compounds and a novel cyclic

1999-02-05

2000-03-28

Lankford, Jr., Leon B.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Using a micro-organism to make a protein or polypeptide

435117, 435120, 435132, 435135, 435136, 435171, 530300, 530317, C07K 1102, C07K 1100, C07K 406, C07K 512

Patent

active

060430583

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a fermentative process for the preparation of PF 1022F substance and PF 1022H substance which are known cyclic depsipeptides, and for the preparation of PF 1022G substance which is a novel depsipeptide. This invention further relates to PF 1022G substance as the novel depsipeptide.


BACKGROUND ART

Hitherto, there are known a number of compounds possessing an anthelmintic activity. Among such compounds, destomycin A, hygromycin B, avermectin and others may be exemplified as such known compounds which are products of microorganisms and which have an anthelmintic activity, but they are of a very small minority among the known anthelmintically active compounds. Takagi et al. made investigations earlier to search for the substances having an anthelmintic activity against roundworms living in domestic fowls, and as a result they discovered PF 1022 substance (which may also be called as PF 1022A substance) as a product of a microorganism, and PF 1022 substance is classified under cyclic depsipeptides having an anthelmintic activity (refer to Japanese Patent Application First Publication Kokai Hei 3-35796, Japanese Patent No. 2608479, U.S. Pat. No.5,116,815 and European Patent Application First Publication No. 0382173A2). This PF 1022 substance is the cyclic depsipeptide represented by the following formula (A): ##STR2## wherein Me stands for methyl group Me has the same meaning in the following descriptions given hereinafter.
PF 1022 substance is a cyclic depsipeptide constituted by L--N-methylleucine [(CH.sub.3).sub.2 CHCH.sub.2 CH(NHCH.sub.3)COOH] (Code: H--L--MeLeu--OH), D-lactic acid [CH.sub.3 CH(OH)--COOH] (Code: H--D--Lac--OH) and D-phenyllactic acid [C.sub.6 H.sub.5 CH.sub.2 CH(OH)COOH] (Code: H--D--PhLac--OH), which are bonded with each other through ester- and amido-bonds. PF 1022 substance may also be represented by the following formula (B). Formula (B):
The present inventors further discovered PF 1022B substance, PF 1022C substance and PF 1022D substance as the products of the microorganism, and these substances are PF 1022-related compounds having an anthelmintic activity (refer to Japanese Patent Application First Publication Kokai Hei 5-170749). Further, PF 1022E substance was found as a product of the microorganism (refer to Japanese Patent Application First Publication Kokai Hei 6-184126). The microorganism used here is PF 1022 strain hereinafter described. The structural formulae of PF 1022B to E substances are given in Internationally published specification WO94/19334 (published on 1st September, 1994) of PCT Application PCT/JP94/00252, and in European Patent Application First-published specification No. 0685469A1.
A series of cyclic depsipeptide derivatives which are produced through chemical synthetic processes by the present inventors, as well as some processes for their preparation are described in Japanese Patent Application First Publication Kokai Hei 5-320148 and Japanese Patent Application First Publication Kokai Hei 6-340694 and also in PCT Internationally published specification WO94/19334 mentioned above. Yet further, another series of cyclic depsipeptides prepared by chemical synthesis by Nishiyama et al. and their preparation methods are given in Japanese Patent Application First Publication Kokai Hei 5-229997, Internationally published specification WO93/19053 of PCT Application PCT/JP93/00286, U.S. Pat. No. 5,514,773 and Internationally published specification WO95/07272 of PCT Application PCT/JP94/01446.
In addition, Examples 3 and 8 of the above PCT Internationally published specification WO94/19334 describe PF 1022-002 substance and PF 1022-202 substance, respectively, which were chemically synthesized by the present inventors. PF 1022-002 substance is reported in another name of PF 1022F substance and PF 1022-202 substance is reported in another name of PF 1022H substance in PCT Internationally published specification WO97/11064 (published on Mar. 27, 1997) of PCT Application PCT/JP96/02730(with International filing date: Sep. 20,

REFERENCES:
patent: 5116815 (1992-05-01), Takagi et al.
Sasaki, T. et al., A New Anthelmintic Cyclodepsipeptide, PF 1022A, The Journal of Antibiotics, vol. 45, No. 5, pp692-697, May 1992.

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