Dihydroxyphenylserine

A few experiments were conducted in barbiturate anesthetized cats and dogs wherein DOPA, phenylserine, p-hydroxyphenylserine (DOPS), and 3,4-dihydroxyphenylserine were injected intravenously tjgU isupply was clamped tern-... 

Figure 10. Pressor Response to Intravenous Injection of 10 Mg. of 3,4-Dihydroxyphenylserine into Cat following Record Obtained in Figure 9...

Dopamine was produced by incubating liver microsomes of rabbits with p- and m-tyramine, noradrenaline, and normetanephrine by incubation with w-octopamine, and adrenaline by incubation with p- and w-methyloctop-amine/" The injection of labelled tyramine as well as of labelled octopamine in the intact animal (rat) caused the appearance of labelled noradrenaline and normetanephrine in the urine/ As tyramine is also hydroxylated to octopamine, it is possible that the production of noradrenaline from tyramine not only takes place via its conversion to dopamine, but also via its conversion to octopamine. The possibility that octopamine is produced by the hydroxylation of tyrosine to hydroxyphenylserine with ensuing decarboxylation is under discussion. The production of noradrenaline from 3,4-dihydroxyphenylserine, 192-201) amino-acid so far not discovered in the mammal could be demonstrated both in organ extracts and in intact animals. Finally, a transamination of 3-hydroxy- or 3,4-dihydroxyphenylpyruvate to the corresponding amino-acids (m-tyrosin, dopa), and their decarboxylation to m-tyramine and dopamine was observed in intact animals (cats). For the time being it is impossible to determine the importance of the means of formation of catecholamines which have been referred to here. Of the above-mentioned precursor substances, p- and m-tyramine,( octopamine, ... 

Blaschko, H., Holton, P. and Sloane-Stanley, G. H., The decarboxylation of jff-3,4-dihydroxyphenylserine (noradrenaline carboxylic acid), Brit. J. Pharmacol. 3, 315 (1948). 

Dihydroxyphenylserine is decarboxylated very poorly if at all by kidney preparations. Positive results were obtained only upon incubation with large amounts of kidney extract for periods of up to 5 hours. Under such conditions the formation of arterenol can be demonstrated. On the other hand a rate of decarboxylation of 3,4-dihydroxyphenylserine comparable to that of DOPA has been reported by Sourkes et with beef adrenal homogenates. Thus, it may be concluded that an unsubstituted amino group is necessary for action by DOPA decarboxylase and that the presence of a hydroxy group on the /3-carbon atom reduces the rate of decarboxylation considerably, but not absolutely, by kidney and adrenal medulla. 

Baik, S.-H. and Yoshioka, H., Enhanced synthesis of L-threo-3,4-dihydroxyphenylserine by high-density wholethreonine aldolase from Strepiomyces avermitilis. Biotechnol. Lett. 2009,31 (3), 443 48. 

Enzymatic carbon-carbon bond formation based on the use of recombinanf whole cells was reported by Baik et al. for the synthesis of L-f/irco-3,4-dihydroxyphenylserine, L-tyrco-25 (Scheme 23.10) [5]. This type of L-amino acid is of interesf due to ifs use for the treatment of Parkinson s disease. The reaction is straightforward sfarfing from 3,4-dihydroxybenzaldehyde and glycine, which are utilized in nonprotected form. In... 

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