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ChemicalBook CAS DataBase List 5-Hydroxytryptophan
56-69-9

5-Hydroxytryptophan synthesis

4synthesis methods
The synthesis of 5-hydroxytryptophan (5-HTP) by the condensation of 5-benzyloxygramine with diethyl formaminomalonate, followed by saponification, decarboxylation, and hydrogenolysis was described in 1951 and 1954 and was an application of gramine synthesis, developed by Snyder and Smith ten years before. A few years later, another application of gramine synthesis was reported. In the same year, Frangatos and Chubb reported an application of the convenient tryptophan synthesis developed ten years before by eliminating the difficult and tedious preparation of 5-benzyloxyindole. The p-benzyloxyphenylhydrazone of γ,γ-dicarbethoxy-γ-acetamido-butyraldehyde (I) was prepared and cyclized, without isolation, to form ethyl β-(5-benzyloxyindol-3-)-αcarbethoxy-α-acetamidopropioilate (II). Saponification and partial decarboxylation of II, followed by hydrolysis of the acetamido group, gave 5-benzyloxytryptophan (III). 5-HTP was obtained by hydrogenolysis of III (Figure 1). However, this synthetic method suffers from the difficulty involved in the regioselective hydroxylation of tryptophan.
synthesis of 5-hydroxytryptophan
synthesis of 5-hydroxytryptophan (5-HTP)
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Yield:-

Reaction Conditions:

with potassium hydroxide in waterRate constant;Equilibrium constant;Irradiation;

References:

Steenken, S.;Neta, P. [Journal of Physical Chemistry,1982,vol. 86,p. 3661 - 3667]

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