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Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.
Phenylglyoxal was first prepared by thermal decomposition of the sulfite derivative of the oxime: [5]. C 6 H 5 C(O)CH(NOSO 2 H) + 2 H 2 O → C 6 H 5 C(O)CHO + NH 4 HSO 4. More conveniently, it can be prepared from methyl benzoate by reaction with KCH 2 S(O)CH 3 to give PhC(O)CH(SCH 3)(OH), which is oxidized with copper(II) acetate. [6]
In organic chemistry, a cyanohydrin reaction is an organic reaction in which an aldehyde (−CH=O) or ketone (>C=O) reacts with a cyanide anion (N≡C −) or a nitrile (−C≡N) to form a cyanohydrin (>C(OH)C≡N).
[3] [4] In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. [3] [4] [5] The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids.
[4] [5] The reaction has since been extended to the synthesis of β-keto esters from the condensation between aldehydes and diazo esters. [6] The general reaction scheme is as follows: General Scheme for Buchner Reaction. The reaction yields two possible carbonyl compounds (I and II) along with an epoxide (III). The ratio of the products is ...
In enzymology, a phenylacetaldehyde dehydrogenase (EC 1.2.1.39) is an enzyme that catalyzes the chemical reaction. phenylacetaldehyde + NAD + + H 2 O phenylacetate + NADH + 2 H +. The 3 substrates of this enzyme are phenylacetaldehyde, NAD +, and H 2 O, whereas its 3 products are phenylacetate, NADH, and H +.
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Examples of aldol reactions in biochemistry include the splitting of fructose-1,6-bisphosphate into dihydroxyacetone and glyceraldehyde-3-phosphate in the fourth stage of glycolysis, which is an example of a reverse ("retro") aldol reaction catalyzed by the enzyme aldolase A (also known as fructose-1,6-bisphosphate aldolase).