Process for the preparation of substituted aryl lactic acid cont

Details Process for the preparation of substituted aryl lactic acid cont Process for the preparation of substituted aryl lactic acid cont

1998-06-04

2000-03-07

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

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

Using a micro-organism to make a protein or polypeptide

514 11, 530317, 530321, 435171, 4352541, 435911, C12P 2104, C12P 102

Patent

active

060338792

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a new process for the preparation of substituted aryllactic acid-containing cyclodepsipeptides having 24 ring atoms, some of which are known.
The preparation of various cyclic, aryllactic acid-containing depsipeptides having 24 ring atoms by microbial processes, for example PF 1022A, PF 1022 B, PF 1022 C, PF 1022D and PF 1022E, has already been described (cf. fermentation of cyclooctadepsipeptides: PF 1022A from Mycelia sterilia (FERM BP-2671; former designation FERM P-10 504) in EP-OS (European Published Specification) 382 173; T. Sasaki et al., J. Antibiotics 45, 1992, pp. 692-697; from the same culture were isolated: PF 1022B, PF 1022C and PF 1022D; JP-Pat. 5 170 749; PF 1022E: JP-Pat. 6 184 126).
The compounds of the PF 1022 series have the following formula (I):


______________________________________ (I) ##STR2## Designation R.sup.1 R.sup.2 R.sup.3 R.sup.4 ______________________________________ PF 1022A --H --Methyl --Benzyl --Methyl PF 1022B --H --Benzyl --Benzyl --Benzyl PF 1022C --H --Methyl --Benzyl --Benzyl PF 1022D --H --Methyl --Methyl --Methyl PF 1022E 4-Hydroxy --Methyl --Benzyl --Methyl ______________________________________
It has also already been disclosed that a number of cyclic, aryllactic acid-containing depsipeptides having 24 ring atoms can be prepared by means of chemical synthetic processes (cf. total syntheses of cyclooctadepsipeptides: JP Pat. 5 229 997; JP Pat. 5 320 1 48; Makoto Ohyama et al., Biosci. Biotech. Biochem. 58 (6), 1994, pp. 1193-1194; Makio Kobayshi et al., Annu. Rep. Sankyo Res. Lab. 46, 1994, pp. 67-75; Stephen J. Nelson et al., J. Antibiotics 47, (11), 1994, pp. 1322-1327; J. Scherkenbeck et al. Tetrahedron 51 (31), 1995, pp. 8459-8470 [PF 1022A]; WO 94/19334; WO 95/19053; EP-OS [European Published Specification] 634 408; EP-OS [European Published Specification] 626 375; EP-OS [European Published Specification] 626 376).
It is furthermore known that certain aryllactic acid-containing cyclodepsipeptides having 24 ring atoms can be used as endoparasiticides (cf. e.g.: EP-OS [European Published Specification] 382; EP-OS [European Published Specification] 503 538;
WO 93/19053; EP-OS [European Published Specification] 0 634 408; WO 94/19334; WO 95/07272; EP-OS [European Published Specification] 626 375; EP-OS [European Published Specification] 626 376).
While chemical synthetic processes make possible a wide variation of the substituent R.sup.1 in the phenyllactic acid fragment of certain cyclooctadepsipeptides (cf.: WO 94/19334; WO 95/19053; EP-OS [European Published Specification] 634 408; EP-OS [European Published Specification] 626 375; EP-OS [European Published Specification] 626 376), until now in the microbial processes only the unsubstituted D-phenyllactic acid-containing cyclooctadepsipeptides preferably resulted (R.sup.1 =-H; cf.: PF 1022A, PF 1022B, PF 1022C and PF 1022D).
Apart from the already-mentioned fermentation of the D-(4-hydroxyphenyl)lactic acid-containing cyclooctadepsipeptide PF 1022E (R.sup.1 =4-hydroxy; cf.: JP Pat. 6 184 126), the fermentative preparation of other, substituted aryllactic acid-containing cyclooctadepsipeptides has thus not been disclosed until now.
The present invention therefore relates to a process for the preparation of substituted aryllactic acid-containing cyclodepsipeptides having 24 ring atoms with the aid of fungal strains of the species Agonomycetales or enzymatic preparations isolated therefrom.
In the process according to the invention, the substituted aryllactic acid-containing cyclodepsipeptides having 24 ring atoms of the general formula (I) ##STR3## in which R.sup.1 represents straight-chain or branched alkyl, cyclic alkyl, alkenyl, alkoxy, alkenyloxy, arylalkoxy, cycloalkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, heteroarylcarbonyl, alkoxysulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, heteroaryl

REFERENCES:
patent: 4879223 (1989-11-01), Miyazawa et al.
patent: 5116815 (1992-05-01), Takagi et al.
patent: 5747448 (1998-05-01), Ohyama et al.
patent: 5763221 (1998-06-01), Aoyagi et al.
Database WPI, Section Ch, Week 9431, Derwent Publications Ltd., AN 94-252800 XP002026183 & JP 06 184 126 A Jul. 5, 1994.
Chemical Abstracts, vol. 117, No. 7, Aug. 17, 1992, Abstract No. 62356, Sasaki, Toru, et al. "A new anthelmintic . . . PF1022A" XP002026182 see abstract and J. Antibiot. (1992), 45(5), 692-7 CODEN: JANTAJ;ISSN: 0021-8820.
Biosci., Biotechnol., Biochem. (1993), 57(1), 98-101 CODEN: BBBIEJ, XP002026181 Kawazu, Kazuyoshi, et al. "Isolation and . . . D1084".

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