1604-49-5

Usage

Uses

Used in Pharmaceutical Industry:
N-TFA-L-TRYPTOPHAN METHYL ESTER is used as an intermediate in the synthesis of tryptophan-containing peptides for various pharmaceutical applications. Its role in the synthesis process is crucial, as it allows for the creation of complex peptide structures with potential therapeutic properties.
Used in Research and Development:
In the field of research and development, N-TFA-L-TRYPTOPHAN METHYL ESTER serves as a valuable compound for studying the properties and interactions of tryptophan-containing peptides. This knowledge can be applied to the design and development of new drugs and therapies targeting various diseases and conditions.
Used in Chemical Synthesis:
N-TFA-L-TRYPTOPHAN METHYL ESTER is also utilized in chemical synthesis processes, where its unique functional groups can be employed to create a wide range of novel compounds with diverse applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 4299-70-1 L-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 1198605-52-5 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 146645-63-8 (2S)-2-amino-3-(1-tert-butoxycarbonylindol-3-yl)propanoic acid 
• 143824-78-6 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester 
• 89311-52-4 2-Amino-3-(2-bromo-1H-indol-3-yl)-propionic acid 
• 89311-53-5 2-Chlorotryptophan 
• 1217265-48-9 methyl (2S)-2-acetamido-3-[2-(4-methoxyphenyl)-1H-indol-3-yl]propanoate 
• 1363260-61-0 methyl (2S)-3-(2-phenyl-1H-indol-3-yl)-2-(trifluoroacetamido)-propanoate 
• 89311-52-4 2-bromo-L-tryptophan 
• 89311-53-5 2-chloro-L-tryptophan 
• 116857-23-9 2-nitro-L-tryptophan 

Relevant academic research and scientific papers

Synthesis of C-Mannosylated Glycopeptides Enabled by Ni-Catalyzed Photoreductive Cross-Coupling Reactions

The biological functions of tryptophan C-mannosylation are poorly understood, in part, due to a dearth of methods for preparing pure glycopeptides and glycoproteins with this modification. To address this issue, efficient and scalable methods are required for installing this protein modification. Here, we describe unique Ni-catalyzed cross-coupling conditions that utilize photocatalysis or a Hantzsch ester photoreductant to couple glycosyl halides with (hetero)aryl bromides, thereby enabling the α-C-mannosylation of 2-bromo-tryptophan, peptides thereof, and (hetero)aryl bromides more generally. We also report that 2-(α-d-mannopyranosyl)-L-tryptophan undergoes facile anomerization in the presence of acid: something that must be considered when preparing and handling peptides with this modification. These developments enabled the first automated solid-phase peptide syntheses of C-mannosylated glycopeptides, which we used to map the epitope of an antibody, as well as providing the first verified synthesis of Carmo-HrTH-I, a C-mannosylated insect hormone. To complement this approach, we also performed late-stage tryptophan C-mannosylation on a diverse array of peptides, demonstrating the broad scope and utility of this methodology for preparing glycopeptides.

A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan

A metal-free 2-selenylation of tryptophan derivatives is reported, where the use of iodide as the catalyst and oxone as the oxidant is key to obtain high yields. Various functional groups within the di-seleny and the indole ring are tolerated, and no racemization is generally observed.

Method for preparing pharmaceutical intermediate of tryptophan derivative

The synthesis method comprises the following steps: L - tryptophan derivatives are taken as starting materials, and esterification is carried out in sequence. The amidation, Boc protection, hydrolysis, amidation or sequential esterification, amidation, Boc protection, hydrogenation, hydrolysis, amidation yields a target product, a tryptophan derivative pharmaceutical intermediate. The preparation method has the advantages of cheap and easily available raw materials, environment friendliness, less process three wastes, accords with the idea of green pharmacy, mild reaction conditions, simple process, simple and convenient operation, high yield and purity and easy amplification and production.

Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions

Herein, we report a practical synthesis of 2-D-l-tryptophan via sequential Ir-catalyzed C–H borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc and methyl ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D-L-Tryptophan is stable in many buffers used for biological studies.

Cyclotryptophan Mycotoxins: Short Synthesis of the Desymmetrized meso -Chimonantine Core of Leptosin C

The desymmetrized meso-chimonantine core of leptosin C was prepared in a short stereoselective convergent sequence in 5 steps as the longest linear path from methyl l-tryptophan hydrochloride as starting material. The key step of this approach was a diastereoselective [4+2] cycloaddition between the bromooxindole and tryptophan derivatives allowing to define the adjacent quaternary benzylic centers in a high chemical yield.

Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

Pd-mediated C-H bond functionalisation protocols have been designed and developed on tryptophan derivatives and tryptophan-containing peptides. The examination of different arylation reactions (three sets of different conditions A-C), all of which are notable for their low temperatures (≤40°C), allowed identification of unified and complementary synthetic approaches toward a series of functionalised tryptophan-containing products. Tryptophan-containing peptides demonstrated to be susceptible to aromatic oxidation were successfully and selectively modified through the application of diaryliodonium salts in good yields.

The biomimetic synthesis of marine alkaloid related pyrido-and pyrrolo[2,3,4-kl]acridines

A biomimetic reaction between β,β′-diamenoketones (e.g. kynuramine, kynurenine or o,o′-diaminobenzophenone) and a variety cyclohexanediones and quinones leading to pyrido[2,3,4-kl) acridines is described. The synthesis of several di- and tetrahydro-pyrido[2,3,4-kl)acridine derivatives (7, 10. 12 and 15) as well as benzoderivatives of the marine alkaloids eilatin (1) and ascididemin (2), compounds 28 and 30, has been accomplished. Additionally, the new heterocycles isoeilatin (24), and diazapentacene 19 have also been synthesized. All newly prepared heterocycles have been fully characterized by IR, MS and mainly by NMR spectroscopy. An analogous synthesis has been developed for pyrrolo[2,3,4-kl)acridines, the heterocyclic core of the bioactive marine alkaloids the plakinidines (31 A-C).

Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone

When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri