Influence of nucleophiles on the high-temperature aqueous isomerization of cis- to trans-cinnamic acid

Reed, Gregg Arthur; Dimmel, Donald R.; Malcolm, Earl W.

doi:10.1021/jo00075a034

Cited by 16 publications

(7 citation statements)

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“…Challenging targets for optimisation are an enhanced catalytic rate and an increased selectivity towards b-addition. [30] and (Z)-cinnamic acid [31] were prepared according to literature procedures.…”

Section: Discussionmentioning

confidence: 99%

Enzymatic Synthesis of Enantiopure α‐ and β‐Amino Acids by Phenylalanine Aminomutase‐Catalysed Amination of Cinnamic Acid Derivatives

Szymański

Wietzes

et al. 2009

ChemBioChem

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The phenylalanine aminomutase (PAM) from Taxus chinensis catalyses the conversion of alpha-phenylalanine to beta-phenylalanine, an important step in the biosynthesis of the N-benzoyl phenylisoserinoyl side-chain of the anticancer drug taxol. Mechanistic studies on PAM have suggested that (E)-cinnamic acid is an intermediate in the mutase reaction and that it can be released from the enzyme's active site. Here we describe a novel synthetic strategy that is based on the finding that ring-substituted (E)-cinnamic acids can serve as a substrate in PAM-catalysed ammonia addition reactions for the biocatalytic production of several important beta-amino acids. The enzyme has a broad substrate range and a high enantioselectivity with cinnamic acid derivatives; this allows the synthesis of several non-natural aromatic alpha- and beta-amino acids in excellent enantiomeric excess (ee >99 %). The internal 5-methylene-3,5-dihydroimidazol-4-one (MIO) cofactor is essential for the PAM-catalysed amination reactions. The regioselectivity of amination reactions was influenced by the nature of the ring substituent.

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Section: Discussionmentioning

confidence: 99%

Enzymatic Synthesis of Enantiopure α‐ and β‐Amino Acids by Phenylalanine Aminomutase‐Catalysed Amination of Cinnamic Acid Derivatives

Szymański

Wietzes

et al. 2009

ChemBioChem

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“…An alternative method of synthesis of cis-CA by hydrogenation was from a solution of ethyl phenylpropiolate, lindlar catalyst and quinoline, which was warmed and flushed with hydrogen (Reed et al, 1993). The ester produced, was then refluxed in a mixture of ethanol-NaOH, the solution was acidified and finally extracted with organic solvents.…”

Section: Cis-cinnamic Acids Synthesis In Vitromentioning

confidence: 99%

High Purity cis-Cinnamic Acid Preparation for Studying Physiological Role of trans-Cinnamic and cis-Cinnamic Acids in Higher Plants

Salum

Erra‐Balsells

2013

Environmental Control in Biology

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Cinnamic acids are present in all kinds of plant tissues and as consequence in herbs and derived medicines, cosmetics, foods, etc. The interest in study their role in nature and possible health effect on consumers has grown exponentially. Because of their molecular structure they can exist in both trans-and cis-forms, having both found in plants. However, as only the trans-forms are commercially available very few studies in vitro and in vivo of the cis-role are available. In the present review the current knowledge in this field of studies is summarized including the brief description of a new tool for easy and friendly synthesis of cis-cinnamic acids by researchers in order to be able to conduct new experiments.

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“…in 1,2-dichloroethane (DCE) at 110 1C for 12 h, which only generated the mono-substituted alkenylation product 3a in 17% yield (Table 1, entry 1). The structure of 3a was indirectly confirmed by the hydrolysis of 3a into its carboxylic acid 4a in NaOH-CH 3 OH, 12 and the structure of 4a was further determined by X-ray single crystal analysis, as described in Scheme 2 (details in ESI †). After that, the use of anhydrous Cu(OAc) 2 was investigated in the model reaction under a nitrogen atmosphere, and 29% of 3a was isolated (Table 1, entry 2).…”

mentioning

confidence: 99%

Ruthenium-catalyzed alkenylation of azoxybenzenes with alkenes through ortho-selective C–H activation

Xie

Wang

2014

Chem. Commun.

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Influence of nucleophiles on the high-temperature aqueous isomerization of cis- to trans-cinnamic acid

Cited by 16 publications

References 0 publications

Enzymatic Synthesis of Enantiopure α‐ and β‐Amino Acids by Phenylalanine Aminomutase‐Catalysed Amination of Cinnamic Acid Derivatives

Enzymatic Synthesis of Enantiopure α‐ and β‐Amino Acids by Phenylalanine Aminomutase‐Catalysed Amination of Cinnamic Acid Derivatives

High Purity cis-Cinnamic Acid Preparation for Studying Physiological Role of trans-Cinnamic and cis-Cinnamic Acids in Higher Plants

Ruthenium-catalyzed alkenylation of azoxybenzenes with alkenes through ortho-selective C–H activation

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