5-Hydroxytryptophan structure

Therapautic Function Antidepressant, antiepileptic Chemicel Name 5-Hydroxytryptophan Common Name 5-Hydroxytryptophan Structural Formula ... 

As a result, we could open the door to a new frontier in indole chemistry. Various 1-hydroxyindoles (4a), l-hydroxytryptophans(la), 1-hydroxytryptamines (lb), and their derivatives have been given birth for the first time. As predicted, 1-hydroxytryptophan and 1-hydroxytryptamine derivatives are found to undergo previously unknown nucleophilic substitution reactions. In addition, we have been uncovering many interesting reactivities characteristic of 1-hydroxyindole structures. From the synthetic point of view, useful building blocks for indole alkaloids, hither to inaccessible by the well-known electrophilic reactions in indole chemistry, have now become readily available. Many biologically interesting compounds have been prepared as well. 

Regioselective nucleophilic substitution at the 5 position is proved to occur when 1-hydroxytryptophan and -tryptamine derivatives are treated with 85% HCOOH (99H1157). Truly amazing is the fact that only substrates carrying a C—C—N structure in the side chain at the 3 position can undergo this regioselective substitution. 

The stereochemistry of the modified tryptophan amino acids in the previously known konbamide and keramamide A sponge metabolites (/ ) has been determined to be l for both 2-bromo-5 -hydroxytryptophan and 6-chi oro-5 - hydro x v-/V-methyltryptophan, respectively (1066). However, based on synthetic studies, doubt has been raised as to the structure of konbamide (1067). A series of investigations of Okinawan Theonella sp. sponges has uncovered the new halo-genated keramamides, E (1031), H (1032) (1068), L (1033) (1069), M (1034), and N (1035) (1070). 

Schmidt U, Weinbrenner S (1996) What is the Structure of the Calmodulin Antagonist Konbamide from Theonella sp. Synthesis of Two Isomers by Direct Biomimetic Introduction of Bromine in Hydroxytryptophan-Containing Cyclic Peptides. Angew Chem Int Ed Engl 35 1336... 

Some patients with EMS reported no history of tryptophan ingestion. An EMS-like syndrome has been associated with use of L-5-hydroxytryptophan (5-FTTP). FFPLC analysis of the 5-FiTP that might have caused the symptoms revealed the presence of an impurity not present in J-FTTP preparations that did not cause symptoms. The structure of the impurity has not been reported. In addition, a recent pharmacoepidemiological study in Canada identified several EMS patients with no history of tryptophan ingestion. These reports suggest that factors other than tryptophan ingestion can lead to the induction of EMS or EMS-like diseases. 

A plausible hypothesis at this stage (about 1943) was that a sequence occurred tryptophan —> an intermediate kynurenine kynurenic acid. It was thought that the intermediate between tryptophan and kynurenine might be the so-called a-hydroxytryptophan (for structure see p. 83), which had been obtained (917) on hydrolysis of phalloidine, a toxic peptide from the fungus Amanita pkalloides (567) such a pathway received... 

Wong C-Y, Eftink M R (1997). Biosynthetic incorporation of tryptophan analogues into staphylococcal nuclease Effect of 5-hydroxytryptophan and 7-azatryptophan on structure and stability. Protein Sci. 6 689-697. 

In contrast, substrates having other structural types of side chain at the 3 position dimerize under acidic conditions, and never produce the 5-substituted products. These facts seem to support the 1-Hydroxyindole Hypotheses, which claim the formation of serotonin from 1-hydroxytryptophan and/or -tryptamine in the acidic compartment within eukaryotic cells. 

The formation of diastereomers of 4-[4 -(6-hydroxyquinolyl)]-5-hydroxytryptophan (27) upon oxidation of 5-HTPP is a rather unusual reaction. It seems unlikely that these diastereomers would be formed from different intermediates than are the 4,4 -dimers (14) or tryptophan-4,5-dione (17). The structures of the indole-quinoline dimers suggest that the C(4)-position of one 5-HTPP residue must attack the C(3)-position of another residue. There are several ways that a coupling of 5-HTPP residues would occur. It was originally proposed that quinone imine 15 is... 

In this article the term oxindole has been used instead of 2-hydroxy-indole , in accordance with Dalgliesh and coworkers 85), who reported that the absorption data suggest that the structure of the hydroxy derivative of tryptophan is best represented by a lactam structure the term hydroxytryptophan is therefore misleading and should be replaced by oxindolylalanine . 

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