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Biological Production of Cinnamoyl Anthranilates
EIB-2923

APPLICATIONS OF TECHNOLOGY:

ADVANTAGES:

ABSTRACT:

Dominique Loqué and Aymerick Eudes of the Joint BioEnergy Institute have developed a method for biologically producing Tranilast and other cinnamoyl anthranilates using a genetically engineered food-grade yeast, Saccharomyces cerevisiae. Tranilast is an antihistamine produced chemically and used in Japan and South Korea to treat asthma and various allergy-associated diseases.

Cinnamoyl anthranilates other than Tranilast are either extracted from oat seeds or produced chemically and have antioxidant, antigenotoxic, and antifibrotic activity. The new method produces these substances at less expense, without the environmental toxins typically associated with chemical synthesis, and more rapidly than current methods, since the molecules produced are secreted in the growing media. The process is expected to scale up without losing the advantages over current production methods.

The JBEI scientists genetically modified Saccharomyces cerevisiae to express two enzymes found in certain plants: (i) 4-coumarate:coenzyme A ligase (referred to as “4CL5”) and (ii) hydroxycinnamoyl/benzoyl-CoA:antrhanilate N-hydroxycinnamoyl/benzoyltranferase (referred to as “HCBT”). These enzymes catalyze two sequential reactions that ultimately produce cinnamoyl anthranilates from cinnamic acids and anthranilate derivatives. The enzymes can act on different substrates, so that the same genetically modified yeast can produce various cinnamoyl anthranilates, depending on which precursors are provided in the culture medium. In experiments under non-optimized production conditions, the yeast was grown for 15 hours with several precursors and readily produced tranilast and 26 of its analogs.

The JBEI method opens the door for eco-friendly, inexpensive production of a group of chemicals useful in medical therapy and life sciences research.

The Joint BioEnergy Institute (JBEI, www.jbei.org) is a scientific partnership led by the Lawrence Berkeley National Laboratory and including the Sandia National Laboratories, the University of California campuses of Berkeley and Davis, the Carnegie Institution for Science and the Lawrence Livermore National Laboratory. JBEI’s primary scientific mission is to advance the development of the next generation of biofuels.

DEVELOPMENT STAGE: Proof of concept.

STATUS: Patent pending. Available for licensing or collaborative research.

FOR MORE INFORMATION:

Eudes A., E.E.K. Baidoo, F. Yang, H. Burd, M.Z. Hadi, F.W. Collins, J.D. Keasling, D. Loqué. “Production of tranilast [N-(3′,4′-dimethyoxycinnamoyl)-anthranilic acid] and its analogs in yeast Saccharomyces cerevisae,” Appl Microbiol Biotechnol. DOI: 10.1007 /s00253-010-2939-y (Oct. 24, 2010).

SEE THESE OTHER BERKELEY LAB TECHNOLOGIES IN THIS FIELD:

Novel Biosynthetic Pathway for Production of Fatty Acid Derived Molecules, IB-2386, IB-2387

Methods and Proteins for Developing New Classes of Antibiotics, IB-2346

Synthetic Peptide that Causes Bundling of F-Actin in Vitro and in Situ, IB-1571

REFERENCE NUMBER: EIB-2923

 

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Last updated: 03/01/2011