Microbiological process for the preparation of (S,S)-N,N'-ethyle

Details Microbiological process for the preparation of (S,S)-N,N'-ethyle Microbiological process for the preparation of (S,S)-N,N'-ethyle

1997-11-17

1999-02-23

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

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

Preparing nitrogen-containing organic compound

435280, 4352521, 435822, C12P 1300

Patent

active

058742620

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a microbiological process for the preparation of (S,S)-N,N'-ethylenediaminedisuccinic acid (abbreviated to "EDDS" hereinafter).
Ethylenediaminetetraacetic acid (EDTA) and nitrilotriacetic acid (NTA) are used on a large scale as complexing agents in household detergents. However, these known complexing agents have very low biodegradability and are not retained in the usual biological treatment of waste water. It is known that the (S,S) configuration of EDDS has good properties as a complexing agent and, at the same time, is biodegradable. This compound could therefore be used as an alternative to EDTA and NTA, provided that this complexing agent can be prepared in a cost-effective process.
EDDS has two asymmetric carbon atoms. Various stereoisomeric forms of the compound are therefore possible. The (S,S) configuration of EDDS corresponds to the formula ##STR2## A cost-effective chemical synthesis leads to a mixture of the three forms S,S; R,R; and meso-EDDS. However, separation of these stereoisomeric compounds requires great industrial complexity. The direct routes disclosed to date for synthesising (S,S)-EDDS are based on starting materials which do not per se permit the product to be justified in terms of cost.
T. Nishikiori et al. have found an actinomyces strain which is able to produce optically pure (S,S)-EDDS (T. Nishikiori et al., Production by Actinomycetes of (S,S)-N,N'-ethylenediaminedisuccinic acid, an inhibitor of phospholipase c; J.Antibiotics 37, 426-427 (1984)). (S,S)-EDDS was isolated from an actinomyces strain (MG 417-CF 17) in the search for inhibitors of phospholipase C. On cultivation of the strain on a complex nutrient medium comprising 1.5% cottonseed meal, 1.5% glycerol, 2% L-asparagine and 0.3% sodium chloride, however, only low yields of 170 mg/l EDDS were obtained. In addition, the isolation is very elaborate and requires several stages.
The object of the present invention is therefore to provide a simple and cost-effective microbiological process for the preparation of optically pure (S,S)-EDDS.
It has now been found, surprisingly, that the yield of (S,S)-EDDS can be increased, and the work up can be considerably simplified, when certain optimised fermentation conditions are observed in a microbiological preparation process.
The present invention therefore relates to a microbiological process for the preparation of N,N'-ethylenediaminedisuccinic acid of the formula (1) by
(a) Precultivation of a strain of the genus Amycolatopsis on a specified nutrient medium (1st preculture),
(b) Inoculation of a nutrient solution of the same composition as the base of the production fermenter by the 1st preculture (2nd preculture),
(c) Inoculation of the base nutrient solution in the production fermenter with the 2nd preculture and incubation in accordance with a specified timetable,
(d) Feeding of the production fermenter in the fed-batch process with a feeding solution under aerobic conditions at a pH of from 2 to 8 and at a temperature of from 15.degree. to 40.degree. C., wherein the base nutrient and feeding solutions are free of zinc-containing compounds.
It is possible to use for the precultivation of the strain of Amycolatopsis (1st preculture) used according to the invention either a synthetic or a natural medium which comprises the nutrients necessary for growth of the microorganisms. For the purpose of the present invention, the precultivation is carried out in an aqueous nutrient medium which comprises as carbon source a carbohydrate such as, for example, glucose, galactose, sucrose, soya flour etc, or preferably polyols such as, for example, glycerol, mannitol, etc. or else a mixture of carbohydrates and polyols.
Examples of suitable nitrogen sources are ammonium hydrogen phosphate, aspartate, glutamate or, where appropriate, urea. Ammonium hydrogen phosphate is preferably used as nitrogen source.
It is furthermore possible to add to the medium inorganic compounds such as, for example, dipotassium hydrogen, potassium dihydrogen, disodium hydrogen or

REFERENCES:
patent: 5707836 (1998-01-01), Endo et al.
APS JPOABS 08-301824 Yamamoto et al. "Production of Biodegradable Chelating Agent as L,L-ethylenediaminedisuccinic Acid and its Alkali Metallic Salt Through Schiff Base of Glyoxal", Nov. 19, 1996.
ATCC "Catalogue of Bacteria & Bacteriophages" 18th Edition 1992 p. 26 Amycolatoopsis Orientalis Ed. Gherna et al.
The Journal of Antibiotics, Apr. 1984, p. 426 Biotechabs, ref. #84-06633.

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