- Preparation method of non-natural L - tryptophan derivative
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The invention discloses a preparation method of a non-natural L - tryptophan derivative, which is sequentially subjected to formylation by adopting a cheap and easily available substituted indole compound as a raw material. Cyclization, ring opening, asym
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- Synthesis method of 7-methyltryptophan
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The invention provides a synthesis method of 7-methyl tryptophan, which comprises the following steps: (1) reacting a compound a with a compound b to obtain a compound 1; (2) reacting the compound 1 with water to obtain a compound 2; (3) reacting the compound 2 with hydrogen to obtain a compound 3; and (4) carrying out hydrolysis reaction on the compound 3 to obtain the 7-methyl tryptophan. The method has the advantages of cheap and accessible raw materials, mild reaction conditions, simple equipment requirements and high safety index, and is suitable for large-scale commercial production. Thetotal yield of the 7-methyl tryptophan prepared by the method is as high as 52.6%, and the purity of the 7-methyl tryptophan is as high as 98%. The invention provides a new choice for the commercialproduction process of the 7-methyl tryptophan medicinal intermediate.
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- Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception
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The noncationizable tripeptide Ac-d-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of d-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.
- De Marco, Rossella,Bedini, Andrea,Spampinato, Santi,Gentilucci, Luca
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supporting information
p. 6861 - 6866
(2014/10/15)
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- Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution
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Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with p = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.
- Gebler, John C.,Woodside, Andrew B.,Poulter, C. Dale
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p. 7354 - 7360
(2007/10/02)
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