Microbial production of methyl anthranilate, a grape flavor compound

Proceedings of the National Academy of Sciences of the United States of America

Volumn 166, Issue 22, 2019, Pages 10749-10756

  Luo, Zi Wei ^a   Cho, Jae Sung ^a   Lee, Sang Yup ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

Corynebacterium glutamicum; Escherichia coli; Metabolic engineering; Methyl anthranilate; Two phase fermentation

Indexed keywords

ANTHRANILIC ACID METHYL ESTER; ANTHRANILIC ACID METHYLTRANSFERASE 1; AROMATIC COMPOUND; ESTER DERIVATIVE; GLUCOSE; GRAPE EXTRACT; METHYLTRANSFERASE; PLANT EXTRACT; S ADENOSYLMETHIONINE; TRIBUTYRIN; UNCLASSIFIED DRUG; VOLATILE AGENT; ANTHRANILIC ACID DERIVATIVE; BACTERIAL PROTEIN; FLAVORING AGENT; PLANT PROTEIN; RECOMBINANT PROTEIN;

ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; BIOENGINEERING; BIOSYNTHESIS; CONTROLLED STUDY; CORYNEBACTERIUM GLUTAMICUM; ESCHERICHIA COLI; FED BATCH CULTURE; FERMENTATION TECHNIQUE; GRAPE; METABOLIC ENGINEERING; MICROBIAL ACTIVITY; NONHUMAN; PLANT METABOLISM; PRIORITY JOURNAL; PROTEIN EXPRESSION; TWO PHASE EXTRACTIVE FERMENTATION; BIOREACTOR; FERMENTATION; GENETICS; METABOLISM; MICROBIOLOGY; PROCEDURES;

BACTERIAL PROTEINS; BIOREACTORS; CORYNEBACTERIUM GLUTAMICUM; ESCHERICHIA COLI; FERMENTATION; FLAVORING AGENTS; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; METHYLTRANSFERASES; ORTHO-AMINOBENZOATES; PLANT PROTEINS; RECOMBINANT PROTEINS;

EID: 85066236098     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1903875116     Document Type: Article

References (29)

1. Wang J, De Luca V (2005) The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including “foxy” methylanthranilate. Plant J 44:606–619.
2. Yadav GD, Krishnan MS (1998) An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol. Org Process Res Dev 2:86–95.
3. Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505–515.
4. Kittleson JR, Pantaleone DP (1994) US Patent 5437991.
5. Taupp M, Harmsen D, Heckel F, Schreier P (2005) Production of natural methyl anthranilate by microbial N-demethylation of N-methyl methyl anthranilate by the topsoil-isolated bacterium Bacillus megaterium. J Agric Food Chem 53:9586–9589.
6. Berger RG, Drawert F, Hadrich S (1988) Microbial sources of flavour compounds. In Bioflavour’87, ed Schreier P (Walter de Gruyter, Berlin).
7. Gross B, et al. (1990) Production of methylanthranilate by the basidiomycete Pycno-porus cinnabarinus (Karst.). Appl Microbiol Biotechnol 34:387–391.
8. Köllner TG, et al. (2010) Herbivore-induced SABATH methyltransferases of maize that methylate anthranilic acid using S-adenosyl-L-methionine. Plant Physiol 153:1795–1807.
9. Yanofsky C, Horn V, Bonner M, Stasiowski S (1971) Polarity and enzyme functions in mutants of the first three genes of the tryptophan operon of Escherichia coli. Genetics 69:409–433.
10. Kim B, Park H, Na D, Lee SY (2014) Metabolic engineering of Escherichia coli for the production of phenol from glucose. Biotechnol J 9:621–629.
11. Ajikumar PK, et al. (2010) Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli. Science 330:70–74.
12. Balderas-Hernández VE, et al. (2009) Metabolic engineering for improving anthranilate synthesis from glucose in Escherichia coli. Microb Cell Fact 8:19.
13. Noda S, Shirai T, Oyama S, Kondo A (2016) Metabolic design of a platform Escherichia coli strain producing various chorismate derivatives. Metab Eng 33:119–129.
14. Dell KA, Frost JW (1993) Identification and removal of impediments to biocatalytic synthesis of aromatics from D-glucose: Rate-limiting enzymes in the common pathway of aromatic amino acid biosynthesis. J Am Chem Soc 115:11581–11589.
15. Gu P, Yang F, Kang J, Wang Q, Qi Q (2012) One-step of tryptophan attenuator inactivation and promoter swapping to improve the production of L-tryptophan in Escherichia coli. Microb Cell Fact 11:30.
16. Kunjapur AM, Hyun JC, Prather KLJ (2016) Deregulation of S-adenosylmethionine biosynthesis and regeneration improves methylation in the E. coli de novo vanillin biosynthesis pathway. Microb Cell Fact 15:61.
17. Loeschcke A, Thies S (2015) Pseudomonas putida—a versatile host for the production of natural products. Appl Microbiol Biotechnol 99:6197–6214.
18. Becker J, Wittmann C (2012) Bio-based production of chemicals, materials and fuels—Corynebacterium glutamicum as versatile cell factory. Curr Opin Biotechnol 23:631–640.
19. Yim SS, An SJ, Kang M, Lee J, Jeong KJ (2013) Isolation of fully synthetic promoters for high-level gene expression in Corynebacterium glutamicum. Biotechnol Bioeng 110: 2959–2969.
20. Shin JH, et al. (2016) Metabolic engineering of Corynebacterium glutamicum for enhanced production of 5-aminovaleric acid. Microb Cell Fact 15:174.
21. Kuepper J, et al. (2015) Metabolic engineering of Pseudomonas putida KT2440 to produce anthranilate from glucose. Front Microbiol 6:1310.
22. Kogure T, Kubota T, Suda M, Hiraga K, Inui M (2016) Metabolic engineering of Corynebacterium glutamicum for shikimate overproduction by growth-arrested cell reaction. Metab Eng 38:204–216.
23. Kitade Y, Hashimoto R, Suda M, Hiraga K, Inui M (2018) Production of 4-hydrox-ybenzoic acid by an aerobic growth-arrested bioprocess using metabolically engineered Corynebacterium glutamicum. Appl Environ Microbiol 84:e02587-17.
24. Kim SY, Lee J, Lee SY (2015) Metabolic engineering of Corynebacterium glutamicum for the production of L-ornithine. Biotechnol Bioeng 112:416–421.
25. Park SH, et al. (2014) Metabolic engineering of Corynebacterium glutamicum for L-arginine production. Nat Commun 5:4618.
26. Han G, Hu X, Qin T, Li Y, Wang X (2016) Metabolic engineering of Corynebacterium glutamicum ATCC13032 to produce S-adenosyl-L-methionine. Enzyme Microb Technol 83:14–21.
27. Lozada-Ramírez JD, Martínez-Martínez I, Sánchez-Ferrer A, García-Carmona F (2008) S-Adenosylhomocysteine hydrolase from Corynebacterium glutamicum: Cloning, overexpression, purification, and biochemical characterization. J Mol Microbiol Biotechnol 15:277–286.
28. Park SY, Yang D, Ha SH, Lee SY (2018) Metabolic engineering of microorganisms for the production of natural compounds. Adv Biosyst 2:1700190.
29. Lee SY, Kim HU (2015) Systems strategies for developing industrial microbial strains. Nat Biotechnol 33:1061–1072.