1604-49-5

Basic information

• Product Name: N-TFA-L-TRYPTOPHAN METHYL ESTER
• Synonyms: N-TFA-L-TRYPTOPHAN METHYL ESTER;(2S)-3-(1H-indol-3-yl)-2-[(2,2,2-trifluoro-1-oxoethyl)amino]propanoic acid methyl ester;(2S)-3-(1H-indol-3-yl)-2-[(2,2,2-trifluoroacetyl)amino]propionic acid methyl ester;methyl (2S)-3-(1H-indol-3-yl)-2-(2,2,2-trifluoroethanoylamino)propanoate;methyl (2S)-3-(1H-indol-3-yl)-2-[(2,2,2-trifluoroacetyl)amino]propanoate
• CAS NO: 1604-49-5
• Molecular Formula: C₁₄H₁₃F₃N₂O₃
• Molecular Weight: 314.2598296
• Mol File: 1604-49-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 461.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.385±0.06 g/cm3(Predicted)
• PKA: 9.66±0.46(Predicted)
• CAS DataBase Reference: N-TFA-L-TRYPTOPHAN METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-TFA-L-TRYPTOPHAN METHYL ESTER(1604-49-5)
• EPA Substance Registry System: N-TFA-L-TRYPTOPHAN METHYL ESTER(1604-49-5)

Safety Data

• Hazardous Substances Data: 1604-49-5(Hazardous Substances Data)

Usage

Description

N-TFA-L-TRYPTOPHAN METHYL ESTER, also known as N-(2,2,2-Trifluoroacetyl)-L-tryptophan Methyl Ester, is a chemical compound derived from the amino acid L-tryptophan. It is characterized by the presence of a trifluoroacetyl group and a methyl ester group, which contribute to its unique chemical properties and reactivity.

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

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

Downstream Products

• 89311-53-5 2-chloro-L-tryptophan 
• 89311-52-4 2-bromo-L-tryptophan 
• 116857-23-9 2-nitro-L-tryptophan 
• 89311-53-5 2-Chlorotryptophan 
• 89311-52-4 2-Amino-3-(2-bromo-1H-indol-3-yl)-propionic acid 
• 1363260-61-0 methyl (2S)-3-(2-phenyl-1H-indol-3-yl)-2-(trifluoroacetamido)-propanoate 
• 1217265-48-9 methyl (2S)-2-acetamido-3-[2-(4-methoxyphenyl)-1H-indol-3-yl]propanoate 
• 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 

Relevant articles and documents

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.

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.

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.