58635-46-4

Basic information

• Product Name: N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER
• Synonyms: N-ALPHA-METHOXYCARBONYL-L-TRYPTOPHAN METHYL ESTER;N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER;N-(Methoxycarbonyl)-l-tryptophan methyl ester ,98%;(S)-Methyl 3-(1H-indol-3-yl)-2-(MethoxycarbonylaMino)propanoate;N-a-methoxycarbonyl-L-tryptophanmethylester
• CAS NO: 58635-46-4
• Molecular Formula: C₁₄H₁₆N₂O₄
• Molecular Weight: 276.29
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis;Tryptophan;Heterocycles
• Mol File: 58635-46-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 99-101 °C(lit.)
• Boiling Point: 494.1°Cat760mmHg
• Flash Point: 252.6°C
• Appearance: /
• Density: 1.273g/cm³
• Vapor Pressure: 6.65E-10mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER(58635-46-4)
• EPA Substance Registry System: N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER(58635-46-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58635-46-4(Hazardous Substances Data)

Usage

Description

N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER, also known as Nα-Methoxycarbonyl L-Tryptophan, is an organic compound derived from the amino acid L-tryptophan. It is a white solid with specific chemical properties that make it a valuable intermediate in various chemical reactions and syntheses. Its structure features a methoxycarbonyl group attached to the nitrogen atom and a methyl ester group attached to the carboxylic acid, which contributes to its reactivity and potential applications.

Uses

Used in Pharmaceutical Industry:
N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER is used as an intermediate in the synthesis of various alkaloids, including (-)-Calycanthine, (+)-Chimonanthine, and (+)-Folicanthine. These alkaloids have potential applications in the development of pharmaceuticals due to their diverse biological activities, such as anti-inflammatory, analgesic, and anti-cancer properties.
Used in Chemical Synthesis:
N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER is used as a key intermediate in the dye-sensitized photooxidation of tryptophan to formylkynurenine. This reaction is significant in the study of tryptophan metabolism and the production of various biologically active compounds.
Used in Research and Development:
As a versatile intermediate, N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER is also used in research and development for the exploration of new synthetic routes and the creation of novel compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C14H16N2O4/c1-19-13(17)12(16-14(18)20-2)7-9-8-15-11-6-4-3-5-10(9)11/h3-6,8,12,15H,7H2,1-2H3,(H,16,18)

Upstream product

• 120-72-9 indole 
• 153381-07-8 (S)-N-methoxycarbonyl aziridine-2-carboxylatemethyl ester 
• 79-22-1 methyl chloroformate 
• 4299-70-1 L-tryptophan methyl ester 
• 7303-49-3 DL-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 79465-86-4 L-(2β,3aβ,8aβ)-8-acetyl-1,2-dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 
• 79465-85-3 L-(2β,3aα,8aα)-8-acetyl-1,2-dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 

Downstream Products

• 126235-85-6 (S)-2-Methoxycarbonylamino-3-(2-phenylselanyl-1H-indol-3-yl)-propionic acid methyl ester 

Relevant articles and documents

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). Thisin situgenerated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.

Synthesis and fungicidal activity of tryptophan analogues–the unexpected calycanthaceous alkaloid derivatives

A series of 21?N-protected tryptophan derivatives were synthesised from tryptophan in good yields. Their structures were characterised by IR,1H NMR,13C NMR, DEPT (90° and 135°) and MS analysis. The synthesised compounds were evaluated against a wide variety of plant pathogen fungi. Compounds a19 and a21 displayed activity against Fusarium oxysporum (F. oxysporum), and compound a21 showed high activity against F. oxysporum and Eggplant Verticillium, with EC50values of 58.27 and 77.39?μg?mL?1, respectively. Considering that the bioassay of the title compounds was evaluated, effects of the chain alkyl substituents may contribute to the significant variations in fungicidal potency. Their structure–antifungal activity relationships were also discussed. These results will pave the way for further design, structural modification and development of calycanthaceous alkaloids as antimicrobial agents.

Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid

The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazol