5-Methoxytryptophan
5-Methoxytryptophan structure
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Common Name | 5-Methoxytryptophan | ||
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| CAS Number | 28052-84-8 | Molecular Weight | 234.251 | |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 478.3±45.0 °C at 760 mmHg | |
| Molecular Formula | C12H14N2O3 | Melting Point | 258-261 °C (dec.)(lit.) | |
| MSDS | Chinese USA | Flash Point | 243.1±28.7 °C | |
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Substrate Oxidation by Indoleamine 2,3-Dioxygenase: EVIDENCE FOR A COMMON REACTION MECHANISM.
J. Biol. Chem. 290 , 30924-30, (2015) The kynurenine pathway is the major route of L-tryptophan (L-Trp) catabolism in biology, leading ultimately to the formation of NAD(+). The initial and rate-limiting step of the kynurenine pathway involves oxidation of L-Trp to N-formylkynurenine. This is an ... |
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Effect of methoxyindole administration on plasma cation levels in the rat.
J. Pineal Res. 6(2) , 141-7, (1989) Administration of methoxyindoles to rats in both the morning and the afternoon caused significant changes in circulating plasma cation levels. All the methoxyindoles except melatonin were without effect at doses below 100 micrograms/kg; the observed changes c... |
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Computational design of a substrate specificity mutant of a protein.
Proteins 26(4) , 459-64, (1996) The wild-type trp repressor of E. coli bound 5-methoxytryptophan, a Trp analogue, less tightly than Trp. A mutant repressor (Val58-->Ala) that should bind 5-methoxytryptophan preferentially to Trp was computationally designed by free-energy calculations accom... |
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Production of methoxyindoles in vitro from methoxytryptophan by rat pineal gland.
J. Pineal Res. 4(1) , 7-11, (1987) Pineal glands were incubated in the presence of [3H] methoxytryptophan with and without methoxamine, epinephrine, and norepinephrine. The beta-adrenoceptor-stimulated pineal glands were capable of converting methoxytryptophan to methoxytryptamine, melatonin, ... |
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Duodenum is not a consistent source of melatonin in rats.
Life Sci. 55(10) , 775-87, (1994) Markedly increased melatonin levels in plasma have been observed in response to tryptophan administration. This post-tryptophan melatonin increase has been attributed to the duodenum. Because extra-pineal sources of melatonin may be important in interpreting ... |
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Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives.
Appl. Microbiol. Biotechnol. 79 , 951-961, (2008) Recently, a gene for a 7-dimethylallyltryptophan synthase (7-DMATS) was identified in Aspergillus fumigatus and its enzymatic function was proven biochemically. In this study, the behaviour of 7-DMATS towards aromatic substrates was investigated and compared ... |
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Control of cyclooxygenase-2 expression and tumorigenesis by endogenous 5-methoxytryptophan.
Proc. Natl. Acad. Sci. U. S. A. 109(33) , 13231-6, (2012) Cyclooxygenase-2 (COX-2) expression is induced by mitogenic and proinflammatory factors. Its overexpression plays a causal role in inflammation and tumorigenesis. COX-2 expression is tightly regulated, but the mechanisms are largely unclear. Here we show the ... |
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Methoxyindole synthesis in the retina of the frog (Rana esculenta) during a diurnal period.
J. Neural Transm. Gen. Sect. 58(3-4) , 223-30, (1983) In the present study, the synthesis of methoxyindoles in the neural part and in the pigment epithelial layer of the retina of the frog eye was investigated on the basis of naturally occurring substrate at regular intervals during a 24 hour period. Melatonin, ... |
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Seasonal variations in HIOMT activity during the night in the pineal gland of 21 day old male Wistar rats.
J. Neural Transm. Gen. Sect. 49(1-2) , 107-16, (1980) In the pineal of 21-day old male Wistar rats hydroxyindole-O-methyltransferase (HIOMT) activities involved in the synthesis of several 5-methoxyindoles were determined during the night in April, June, October and January. A high HIOMT activity for the synthes... |
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The pineal gland of the mole (Talpa europaea L.). VII. Activity of hydroxyindole-O-methyltransferase (HIOMT) in the formation of 5-methoxytryptophan, 5-methoxytryptamine, 5-methoxyindole-3-acetic acid, 5-methoxytryptophol and melantonin in the eyes and the pineal gland.
J. Neural Transm. Gen. Sect. 51(3-4) , 271-82, (1981) Using a method in which no substrate is added to the incubation medium, the capacity of HIOMT to synthesize 5-methoxytryptophan, 5-methoxytryptamine, 5-methoxyindole-3-acetic acid, 5-methoxytryptophol and melatonin has been determined in the pineal and the ey... |