Title:
NEW SOPHOROSELIPIDS, METHOD FOR THEIR PRODUCTION AND USE
Document Type and Number:
WIPO Patent Application WO1999024448
Kind Code:
A3
Abstract:
The invention relates to sophoroselipids of formula (I) wherein R<4> represents H, -CH2CH3, -CH2CH2CH3, n is an integer number from 2 to 27, R<1> and R<2> represent, independently from each other, H or a group of formula (II), and R<3> represents H or -OH. The invention also relates to a method for producing sophoroselipids of formula (I) wherein R<1>, R<2>, R<3> and n have the aforementioned meanings and R<4> represents -CH3, -CH2CH3 or -CH2CH2CH3. According to this method, a yeast capable of secreting a sophoroselipid in the form of a lactone in the culture excess, is fermented in a culture medium containing a glycerin, a succinate, a mono-, di- and/or tri-saccharide and a lipid precursor, said sophoroselipid being then isolated from the culture solution. The inventive method is characterised in that the lipid precursor contains one or more 3-alkanols, 4-alkanols or an alkanone with a chain length from 6 to 30 carbon atoms or mixtures of said alkanols/alkanone. Furthermore, according to a variant of the aforementioned method for producing sophoroselipids of formula (I), wherein R<1>, R<2>, R<3> and n have the meanings aforementioned and R<4> represents -CH3, -CH2CH3 or -CH2CH2CH3, the culture medium is maintained during fermentation under a reduced oxygen concentration. The new sophoroselipids may be used, e.g., as surfactants, cosmetics, disinfecting agents or pharmaceutical products.
Inventors:
LANG SIEGMUND (DE)
BRAKEMEIER ANDREAS (DE)
WULLBRANDT DIETER (DE)
SEIFFERT-STOERIKO ANDREAS (DE)
BRAKEMEIER ANDREAS (DE)
WULLBRANDT DIETER (DE)
SEIFFERT-STOERIKO ANDREAS (DE)
Application Number:
PCT/EP1998/006590
Publication Date:
August 19, 1999
Filing Date:
October 17, 1998
Export Citation:
Assignee:
AVENTIS RES & TECH GMBH & CO (DE)
LANG SIEGMUND (DE)
BRAKEMEIER ANDREAS (DE)
WULLBRANDT DIETER (DE)
SEIFFERT STOERIKO ANDREAS (DE)
LANG SIEGMUND (DE)
BRAKEMEIER ANDREAS (DE)
WULLBRANDT DIETER (DE)
SEIFFERT STOERIKO ANDREAS (DE)
International Classes:
A01N1/00; A01N43/16; C12P19/44; A61K8/06; A61K8/60; A61K8/73; A61K31/70; A61K47/26; A61L2/16; A61Q19/00; C07G3/00; C07H13/06; C07H15/04; C07H15/207; C11D1/66; C11D3/22; C12P19/46; C12R1/72; (IPC1-7): C07H15/04; A61K31/70
Foreign References:
| EP0745608A2 | 1996-12-04 | |||
| US4215213A | 1980-07-29 |
Other References:
CHEMICAL ABSTRACTS, vol. 126, no. 9, 3 March 1997, Columbus, Ohio, US; abstract no. 118152z, K.MORIKAWA ET AL.: "Preparation of Oligosaccharide Glycosides as Antiinflammatory Agents." page 611; column 1; XP002106418
C.HÄLLGREN ET AL.: "Synthesis of Octyl-2-O-a-D-Mannopyranosyl-a-D-Mannopyranoside, its 6'-Phosphate and the Corresponding Monomethyl Phosphodiester : Intermediate Structures in the Biosynthesis of N-Linked Oligosaccharides in Dictyostelium Discoidium.", CARBOHYDRATE RESEARCH., vol. 260, no. 1, 4 July 1994 (1994-07-04), AMSTERDAM NL, pages 63 - 71, XP002106415
V.POZSGAY ET AL.: "Synthesis of a Pentasaccharide Fragment of Polysaccharide II of Mycobacterium tuberculosis.", CARBOHYDRATE RESEARCH., vol. 277, no. 1, 7 November 1995 (1995-11-07), AMSTERDAM NL, pages 51 - 66, XP002106416
M.YUDA ET AL.: "Neolignan Glycosides from Roots of Codonopsis Tangshen", PHYTOCHEMISTRY, vol. 29, no. 6, 1990, pages 1989 - 1993, XP002106417
BRAKEMEIER A ET AL: "NOVEL SOPHOROSE LIPIDS FROM MICROBIAL CONVERSION OF 2-ALKANOLS", BIOTECHNOLOGY LETTERS, vol. 17, no. 11, 1 November 1995 (1995-11-01), pages 1183 - 1188, XP000566808
MATSUMURA S ET AL: "SURFACE ACTIVITIES, FOAM SUPPRESSION, BIODEGRADABILITY AND ANTIMICROBIAL PROPERTIES OF S-ALKYL GLUCOPYRANOSIDES", YUKAGAKU - JOURNAL OF THE JAPAN OIL CHEMISTS' SOCIETY, vol. 40, no. 9, 1 January 1991 (1991-01-01), pages 709 - 714, XP000653016
C.HÄLLGREN ET AL.: "Synthesis of Octyl-2-O-a-D-Mannopyranosyl-a-D-Mannopyranoside, its 6'-Phosphate and the Corresponding Monomethyl Phosphodiester : Intermediate Structures in the Biosynthesis of N-Linked Oligosaccharides in Dictyostelium Discoidium.", CARBOHYDRATE RESEARCH., vol. 260, no. 1, 4 July 1994 (1994-07-04), AMSTERDAM NL, pages 63 - 71, XP002106415
V.POZSGAY ET AL.: "Synthesis of a Pentasaccharide Fragment of Polysaccharide II of Mycobacterium tuberculosis.", CARBOHYDRATE RESEARCH., vol. 277, no. 1, 7 November 1995 (1995-11-07), AMSTERDAM NL, pages 51 - 66, XP002106416
M.YUDA ET AL.: "Neolignan Glycosides from Roots of Codonopsis Tangshen", PHYTOCHEMISTRY, vol. 29, no. 6, 1990, pages 1989 - 1993, XP002106417
BRAKEMEIER A ET AL: "NOVEL SOPHOROSE LIPIDS FROM MICROBIAL CONVERSION OF 2-ALKANOLS", BIOTECHNOLOGY LETTERS, vol. 17, no. 11, 1 November 1995 (1995-11-01), pages 1183 - 1188, XP000566808
MATSUMURA S ET AL: "SURFACE ACTIVITIES, FOAM SUPPRESSION, BIODEGRADABILITY AND ANTIMICROBIAL PROPERTIES OF S-ALKYL GLUCOPYRANOSIDES", YUKAGAKU - JOURNAL OF THE JAPAN OIL CHEMISTS' SOCIETY, vol. 40, no. 9, 1 January 1991 (1991-01-01), pages 709 - 714, XP000653016
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