Sophoroselipids, method for their production and use

Details Sophoroselipids, method for their production and use Sophoroselipids, method for their production and use

2000-07-03

2002-08-13

Riley, Jezia (Department: 1637)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S018600, C536S119000, C536S120000, C536S123100, C536S123130, C536S124000

Reexamination Certificate

active

06433152

ABSTRACT:

The present invention relates to novel sophorose lipids, methods for their biotechnological production and their use as surfactant, cosmetics, disinfectant or pharmaceuticals.
BACKGROUND OF THE INVENTION
Microbial glycolipids have been known for some years as biosurfactants with versatile applications in cosmetics, the detergent and cleaner sector, the foodstuff sector, medicine and environmental protection. Compared with chemical surfactants, because of their biological origin they have advantages such as, for example, lower toxicity and generally better degradability. They are produced by bacteria, yeasts or fungi when grown on long-chain petroleum products, on vegetable oils and fats or derivatives thereof, or on mono- and oligosaccharides. Targeted modification of the molecular structures of these products by altering the carbon source has to date been possible to only a slight extent. Since its discovery in 1961, sophorose lipid has been among the intensively researched microbial glycolipids [P. A. Gorin, J. F. T. Spencer and A. P. Tulloch; Can. J. Chem. 39 (1961), 846-855].
According to various reports, sophorose lipid can be produced by various yeasts of the genus Candida (Torulopsis) as secondary metabolite using a substrate from the carbon sources indicated above. Suitable yeast strains described are
Candida bombicola, Candida bogoriensis, Candida magnoliae, Candida gropengiesser
and
Candida apicola
[R. Hommel, Biodegradation, 1, (1991), 107].
The sophorose lipids produced by the genus Candida have a structure depicted below (1).
Besides this main lactone product with a hydroxy fatty acid which is linked both glycosidically and in the manner of an ester, also found in small amounts are uncyclized intermediates. Depending on the substrate employed, the hydroxy fatty acid can be saturated, mono- or else polyunsaturated. Furthermore, the 6′-O and 6″-O positions of the glucose units are acetylated to varying extents. Only slight differences in the fatty acids in the side chain of the sophorose lipids are found.
To produce a glycolipid with amphiphilic structure, i.e. high surface activity, the sophorose lipid lactones must be converted into the sophorose lipid esters or amides by elaborate synthetic and purification stages [S. Inoue, et al. U.S. Pat. No. 4,215,213, 1990; Y. Ishigami, JP-Application: Toku Kai Hei 6-100581].
It is known that on fermentation of yeasts of the genus Candida using 2-alkanols, in place of vegetable oils and fats, fatty acids or their alkyl esters, it is. possible to obtain uncyclized glucose lipids and sophorose lipids with surface-active properties (see DE 195 18 982.5). The corresponding 2-alkanols are, however, costly or else elaborate to produce. It has not to date been possible to use more cost-effective and more easily obtainable 1-alcohols because it is known that they are to a large extent converted into the corresponding acids before they are transformed into glycolipids (see, for example, D. F. Jones, R. Howe, J.Chem.Soc. -C-, (1968), 2801-2808). There have merely been indications of how to obtain these substances, which have never been isolated or characterized in detail (Davila, A.-M., Marchal, R., Vandecasteele, J.-P., J. lndustr. Microbiol., (1994) 249-257).
SUMMARY OF THE INVENTION
It has now been found, surprisingly, that uncyclized glucose lipids and sophorose lipids with surface-active properties are also obtainable on use of 3-alkanols, 4-alkanols, 2-alkanones, 3-alkanones and 4-alkanones.
In addition, successful use of 1-alcohols and alkanals for obtaining the novel products is possible when the culture medium has a reduced oxygen concentration during fermentation of the microorganisms.
The invention thus relates to compounds of the formula I
in which
R
4
is H, -CH
2
CH
3
, -CH
2
CH
2
CH
3
,
O
n
is an integer from 2 to 27,
R
1
and R
2
are, independently of one another, H or
C
and
CH
3
R
3
is H or -OH.


REFERENCES:
patent: 4215213 (1980-07-01), Inoue et al.
patent: 5767255 (1998-06-01), Wulbrand et al.
patent: 0745608 (1996-12-01), None
Gorin et al., “Hydroxy Fatty Acid Glycosides of Sophorose From Torulopsis Magnoliae”Can J. Chem. vol. 39: pp. 846-854 (1961).
Kirchner et al., “Resolution of Racemic Mixtures via Lipase Catalysis in Organic Solvent”J. Am. Chem. Soc., 107: pp. 7072-7076 (1985).
Hommel, R.K., “Formation and Physiological role of Biosurfactants produced by hydrocarbon-utilizing microorganisms”Biodegradation, 1, pp. 107-119 (1990).
Jones et al., “Microbiological Oxidation of Long-chain Aliphatic Compounds. Part 1. Alkanes and Alk-1-enes”J. Chem. Soc., (C), pp. 2801-2808 (1968).
Davila et al., “Sophorose lipid production from lipidic precursors: predictive evaluation of industrial substrates”Journal of Industrial Microbiology, 13, pp. 249-257 (1994).
Hallgren, C., et al,Carbohydrate Research 260:63-71, XP-002106415 (1994).
Pozsgay, V., et al,Carbohydrate Research 277:51-66, XP-002106416 (1995).
Yuda, M., et al,Phytochemistry 29:1989-1993, XP-002106417 (1990).
Morikawa, K., et al,Chemical Abstracts 126:118152z, XP-002106418 (1997).
Brakemeier, A., et al,Biotechnology Letters 17:1183-1188, XP_000566808 (1995).
Matsumura, S., et al,J. of the Japan Oil Chemists' Society: 40: 709-714, XP-000653016 (1991).

Affiliated with

Also associated with

Rating

Sophoroselipids, method for their production and use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Sophoroselipids, method for their production and use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Sophoroselipids, method for their production and use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2959079