Title:
CYCLIC DIPEPTIDES AS FEEDSTUFF ADDITIVES
Document Type and Number:
WIPO Patent Application WO/2011/147881
Kind Code:
A3
Abstract:
The invention relates to feedstuff additives, containing at least one diketopiperazine having the following general formula (IV), or a salt thereof, where R1 and R2 independently of each other are an amino acid residue R (preferably in the L configuration), selected from the group consisting of methionine (R = - (CH2) 2SCH3), lysine (R = -(CH2)4NH2), threonine (R = -CH (OH) (CH3)), tryptophan (R = -indolyl), histidine (R = -imidazoyl), valine (R = -CH(CH3)2), leucine (R = -CH2CH ( (CH3) 2), isoleucine (R = -CH (CH3) CH2CH3), phenylalanine (R = -CH2Ph), arginine (R = - (CH2) 3NHC (=NH) CH2), cysteine (R = -CH2SH), wherein optionally R1 can be equal to R2; or containing at least one compound having the following general formula (V), or a salt thereof, where R1 and R2 are as defined above; and to the diketopiperazine itself and to a method for producing same.
Inventors:
KOBLER CHRISTOPH (DE)
HAEUSSNER THOMAS (DE)
WECKBECKER CHRISTOPH (DE)
HAEUSSNER THOMAS (DE)
WECKBECKER CHRISTOPH (DE)
Application Number:
PCT/EP2011/058577
Publication Date:
May 24, 2012
Filing Date:
May 25, 2011
Export Citation:
Assignee:
EVONIK DEGUSSA GMBH (DE)
KOBLER CHRISTOPH (DE)
HAEUSSNER THOMAS (DE)
WECKBECKER CHRISTOPH (DE)
KOBLER CHRISTOPH (DE)
HAEUSSNER THOMAS (DE)
WECKBECKER CHRISTOPH (DE)
International Classes:
C07D241/08; A23K1/16
Domestic Patent References:
| WO2009100431A1 | 2009-08-13 | |||
| WO1989006497A1 | 1989-07-27 |
Other References:
LU X. ET AL: "Diketopiperazine constituents of marine bacillus subtilis", CHEMISTRY OF NATURAL COMPOUNDS, vol. 45, no. 2, 1 January 2009 (2009-01-01), pages 290 - 292, XP002658760
DONKOR I.O. ET AL: "SYNTHESIS OF A REPORTED CALPAIN INHIBITOR ISOLATED FROM STREPTOMYCES GRISEUS", BIOORGANI & MEDICINAL CHEMISTRY LETTERS, vol. 11, 1 January 2001 (2001-01-01), pages 2647 - 2649, XP002658761
TAKAYA Y ET AL: "Antioxidant constituents in distillation residue of awamori spirits", J. AGRIC. FOOD CHEM, vol. 55, 13 December 2006 (2006-12-13), pages 75 - 79, XP002658762
STARK T. ET AL: "Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs", J. AGRIC. FOOD CHEM., vol. 53, 9 August 2005 (2005-08-09), pages 7222 - 7231, XP002658763
LOPET LC ET AL: "Explanation of bitter taste of venom of ponerine ant, pachycondyla apicalis", JOURNAL OF CHEMICAL ECOLOGY, vol. 23, 1 January 1997 (1997-01-01), pages 705 - 712, XP002658764
PEREZ-PICASO L. ET AL: "Efficient mocrowave assisted syntheses of 2,5-diketopiperazines in aqueous media", MOLECULES, vol. 14, 31 July 2009 (2009-07-31), pages 2836 - 2849, XP002658765
HUANG Z-Z ET AL: "Biomimetic catalysis of diketopiperazine and dipeptide syntesis", ANGEW. CHEM. INT. ED., vol. 47, 1 January 2008 (2008-01-01), pages 1758 - 1761, XP002658766
BRENNER ET AL: "Isolierung von enzymatisch gebildetem L-Methionyl-L-methionin und L-Methionyl-Lmethionyl-L-methionin; Vergleich mit synthetischen Produkten", HELVETICA CHIMICA ACTA, vol. 34, 1 January 1951 (1951-01-01), pages 2085, XP009152067
DONKOR I.O. ET AL: "SYNTHESIS OF A REPORTED CALPAIN INHIBITOR ISOLATED FROM STREPTOMYCES GRISEUS", BIOORGANI & MEDICINAL CHEMISTRY LETTERS, vol. 11, 1 January 2001 (2001-01-01), pages 2647 - 2649, XP002658761
TAKAYA Y ET AL: "Antioxidant constituents in distillation residue of awamori spirits", J. AGRIC. FOOD CHEM, vol. 55, 13 December 2006 (2006-12-13), pages 75 - 79, XP002658762
STARK T. ET AL: "Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs", J. AGRIC. FOOD CHEM., vol. 53, 9 August 2005 (2005-08-09), pages 7222 - 7231, XP002658763
LOPET LC ET AL: "Explanation of bitter taste of venom of ponerine ant, pachycondyla apicalis", JOURNAL OF CHEMICAL ECOLOGY, vol. 23, 1 January 1997 (1997-01-01), pages 705 - 712, XP002658764
PEREZ-PICASO L. ET AL: "Efficient mocrowave assisted syntheses of 2,5-diketopiperazines in aqueous media", MOLECULES, vol. 14, 31 July 2009 (2009-07-31), pages 2836 - 2849, XP002658765
HUANG Z-Z ET AL: "Biomimetic catalysis of diketopiperazine and dipeptide syntesis", ANGEW. CHEM. INT. ED., vol. 47, 1 January 2008 (2008-01-01), pages 1758 - 1761, XP002658766
BRENNER ET AL: "Isolierung von enzymatisch gebildetem L-Methionyl-L-methionin und L-Methionyl-Lmethionyl-L-methionin; Vergleich mit synthetischen Produkten", HELVETICA CHIMICA ACTA, vol. 34, 1 January 1951 (1951-01-01), pages 2085, XP009152067
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