2016Applied Biological ChemistryOpen access

Bacterial synthesis of four hydroxycinnamic acids

Dae Gyuun An, Mi Na Cha, Saravanan Prabhu Nadarajan, Bong Gyu Kim, Joong‐Hoon Ahn

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Abstract

Hydroxycinnamates are a class of phenolic compounds that have a C6-C3 carbon backbone. Hydroxycinnamic acids are derived from cinnamic acid via hydroxylation or methylation and are found in foods such as pears, coffee beans, and dandelions. They are involved in protection against chemotherapy side effects and the prevention of cardiovascular disease and cancer. We synthesized four types of hydroxycinnamates (p-coumaric acid, cinnamic acid, caffeic acid, and ferulic acid) from glucose in Escherichia coli by introducing different combination of four genes: tyrosine ammonia lyase, phenylalanine ammonia lyase, S.espanaensis monooxygenase, and Oryza sativa O-methyltransferase. The final yields of hydroxycinnamic acids were increased by engineering the metabolic pathway of E. coli. Using these strategies, 100.1 mg/L p-coumaric acid, 138.2 mg/L caffeic acid, 64 mg/L ferulic acid, and 1072.3 mg/L cinnamic acid were synthesized.

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Hydroxycinnamates are a class of phenolic compounds that have a C6-C3 carbon backbone. Hydroxycinnamic acids are derived from cinnamic acid via hydroxylation or methylation and are found in foods such as pears, coffee beans, and dandelions. They are involved in protection against chemotherapy side effects and the prevention of cardiovascular disease and cancer. We synthesized four types of hydroxycinnamates (p-coumaric acid, cinnamic acid, caffeic acid, and ferulic acid) from glucose in Escherichia coli by introducing different combination of four genes: tyrosine ammonia lyase, phenylalanine ammonia lyase, S.espanaensis monooxygenase, and Oryza sativa O-methyltransferase. The final yields of hydroxycinnamic acids were increased by engineering the metabolic pathway of E. coli. Using these strategies, 100.1 mg/L p-coumaric acid, 138.2 mg/L caffeic acid, 64 mg/L ferulic acid, and 1072.3 mg/L cinnamic acid were synthesized.

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Available abstract

Hydroxycinnamates are a class of phenolic compounds that have a C6-C3 carbon backbone. Hydroxycinnamic acids are derived from cinnamic acid via hydroxylation or methylation and are found in foods such as pears, coffee beans, and dandelions. They are involved in protection against chemotherapy side effects and the prevention of cardiovascular disease and cancer. We synthesized four types of hydroxycinnamates (p-coumaric acid, cinnamic acid, caffeic acid, and ferulic acid) from glucose in Escherichia coli by introducing different combination of four genes: tyrosine ammonia lyase, phenylalanine ammonia lyase, S.espanaensis monooxygenase, and Oryza sativa O-methyltransferase. The final yields of hydroxycinnamic acids were increased by engineering the metabolic pathway of E. coli. Using these strategies, 100.1 mg/L p-coumaric acid, 138.2 mg/L caffeic acid, 64 mg/L ferulic acid, and 1072.3 mg/L cinnamic acid were synthesized.

Key concepts: Chemistry, Hydroxycinnamic acid, Cinnamic acid, Ferulic acid, Coumaric acid, Caffeic acid, Biochemistry, Hydroxylation

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