Substituted Phenylalanines and Phenylethylamines<sup>1</sup>

Fennoy, Leon V.

doi:10.1021/jo01069a516

Cited by 12 publications

(2 citation statements)

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“…Dopamine hydrochloride (1, Table 1) was obtained from Koch-Light and re-crystallized. 3-hydroxy-4-methoxyphenethylamine hydrochloride (2) was prepared from isovanillin by reaction with nitromethane to give the w-nitro-styrene (Baxter, Allan & Swan, 1965) which was then reduced with lithium aluminium hydride (Fennoy, 1961). 4-Hydroxy-3-methoxyphenethylamine hydrochloride (3) was prepared by a similar method from vanillin.…”

Section: Compoundsmentioning

confidence: 99%

On the Actions of Compounds Related to Dopamine at a Neurosecretory Synapse

Ginsborg

Turnbull

House

1976

British J Pharmacology

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Royal (Dick) School of Veterinary Studies, Summerhall, Edinburgh EH9 1 QH I The effects of a number of substances related to dopamine, including all its methylated derivatives, were investigated on the membrane potential and response to nerve stimulation of cockroach salivary gland cells. 2 Only N-methyldopamine (epinine), N,N-dimethyldopamine and N,N-dimethylnoradrenaline, all with unsubstituted hydroxyl groups, directly resembled dopamine in producing a hyperpolarization which could be as large as that caused by maximal nerve stimulation. During the continued presence of these substances the hyperpolarization waned and responses to nerve stimulation declined. 3 Many of the compounds caused one or both of two other effects, namely an increase in the rate of 'spontaneous miniature hyperpolarizations' and an enhancement of the submaximal responses to single nerve stimuli. There were no obvious structural requirements for these effects.

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Section: Compoundsmentioning

confidence: 99%

On the Actions of Compounds Related to Dopamine at a Neurosecretory Synapse

Ginsborg

Turnbull

House

1976

British J Pharmacology

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“…Thus to meet market demand, several methods for the production of phenylpropionic acids are developed, mainly including chemical methods and biocatalysis. The most notable chemical method is the reduction and hydrolysis of azlactones; however, this process leads to racemic products, which needs late-stage racemate resolution (Badshah, Khan, & Kidwai, 1972;Fennoy, 1961). In addition, direct functionalization of (S)-α-tyrosine or (S)-αphenylalanine is based on protective group chemistry or needs harsh reagents, such as F 2 or HNO 3 (Dugave, 1995;Vasdev, Chirakal, Schrobilgen, & Nahmias, 2001).…”

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confidence: 99%

Efficient production of phenylpropionic acids by an amino‐group‐transformation biocatalytic cascade

Wang

Song

et al. 2019

Biotech & Bioengineering

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Phenylpropionic acids are commonly used in the synthesis of pharmaceuticals, cosmetics, and fine chemicals. However, the synthesis of phenylpropionic acids faces the challenges of high cost of substrates and a limited range of products. Here, we present an artificially designed amino-group-transformation biocatalytic process, which uses simple phenols, pyruvate, and ammonia to synthesize diverse phenylpropionic acids. This biocatalytic cascade comprises an amino-group-introduction module and three amino-group-transformation modules, and operates in a modular assembly manner. Escherichia coli catalysts coexpressing enzymes from different modules achieve whole-cell simultaneous one-pot transformations of phenols into the corresponding phenylpropionic acids including (S)-α-amino acids, α-keto acids, (R)-αamino acids, and (R)-β-amino acids. With cofactor recycling, protein engineering, and transformation optimization, four (S)-α-amino acids, four α-keto acids, four (R)-αamino acids, and four (R)-β-amino acids are synthesized with good conversion (68-99%) and high enantioselectivities (>98%). Therefore, the amino-grouptransformation concept provides a universal and efficient tool for synthesizing diverse products.

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