21339-55-9

Basic information

• Product Name: L-ABRINE
• Synonyms: N-A-METHYL-L-TRYPTOPHAN;N ALPHA-METHYL-L(+)-TRYPTOPHAN;N-ALPHA-METHYL-L-TRYPTOPHAN;N-METHYLTRYPTOPHAN;N-ME-TRP-OH;N-ME-TRYPTOPHAN;N-METHYL-L-TRYPTOPHAN;1-methyl-l-tryptopha
• CAS NO: 21339-55-9
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• EINECS: 208-388-5
• Product Categories: Indoles and derivatives;Amino Acid Derivatives;Peptide Synthesis;Tryptophan;amino acid
• Mol File: 21339-55-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: >300 °C (dec.)(lit.)
• Boiling Point: 429.3 °C at 760 mmHg
• Flash Point: 213.4 °C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 3.92E-08mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly, Sonicated), DMSO (Sl
• PKA: 2.26±0.10(Predicted)
• CAS DataBase Reference: L-ABRINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-ABRINE(21339-55-9)
• EPA Substance Registry System: L-ABRINE(21339-55-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: YN7135000
• Hazardous Substances Data: 21339-55-9(Hazardous Substances Data)

Usage

Uses

1-Methyl-L-tryptophan can be used:In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N2-arylation of 1,2,3-triazoles.As a key starting material for the total synthesis of (?)-ardeemin.In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.

InChI:InChI=1/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m0/s1

Upstream product

• 603-76-9 1-methylindole 
• 56-45-1 L-serin 
• 73-22-3 L-Tryptophan 
• 74-88-4 methyl iodide 

Downstream Products

• 1334509-86-2 Fmoc-1-Me-Trp-OH 
• 109927-44-8 N^α-(tert-butoxycarbonyl)-1-methyl-L-tryptophan 
• 103943-63-1 N^α-(tert-butoxycarbonyl)-1-methyl-D-tryptophan 
• 1392107-84-4 N-in-methyl-L-tryptophan n-heptyl ester tosylate 
• 1219039-99-2 Nα-[3-(2-cyanophenyl)acryloyl]-1-methyl-L-tryptophan 
• 1219040-02-4 Nα-[2-cyano-3-(2-fluorophenyl)acryloyl]-1-methyl-L-tryptophan 
• 1027965-82-7 {benzyl-[2-benzyloxycarbonylamino-3-(1-methyl-1H-indol-3-yl)-propionyl]-amino}-acetic acid methyl ester 
• 561303-44-4 (2S,5S)-4-benzyl-5-methyl-2-(1-methyl-1H-indol-3-ylmethyl)-3,6-dioxopiperazine-1-carboxylic acid methyl ester 

Relevant articles and documents

Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA

Abstract: The emergence of resistance to frontline antibiotics has called for novel strategies to combat serious pathogenic infections. Methicillin-resistant Staphylococcus aureus [MRSA] is one such pathogen. As opposed to traditional antibiotics, bacteriostatic anti-virulent agents disarm MRSA, without exerting pressure, that cause resistance. Herein, we employed a thermophilic Thermotoga maritima tryptophan synthase (TmTrpB1) enzyme followed by an isonitrile synthase and Fe(II)-α-ketoglutarate-dependent oxygenase, in sequence as biocatalysts to produce antivirulent indole vinyl isonitriles. We report on conversion of simple derivatives of indoles to their C3-vinyl isonitriles, as the enzymes employed here demonstrated broader substrate tolerance. In toto, eight distinct L-Tryptophan derived α-amino acids (7) were converted to their bioactive vinyl isonitriles (3) by action of an isonitrile synthase (WelI1) and an Fe(II)-α-ketoglutarate-dependent oxygenase (WelI3) yielding structural variants possessing antivirulence against MRSA. These indole vinyl isonitriles at 10 μg/mL are effective as antivirulent compounds against MRSA, as evidenced through analysis of rabbit blood hemolysis assay. Based on a homology modelling exercise, of enzyme-substrate complexes, we deduced potential three dimensional alignments of active sites and glean mechanistic insights into the substrate tolerance of the Fe(II)-α-ketoglutarate-dependent oxygenase. Graphic abstract: [Figure not available: see fulltext.]

1-methyl tryptophan synthesis method

The present invention provides a direct and efficient 1-methyl tryptophan synthesis method, and specifically relates to a method for synthesizing 1-methyl tryptophan represented by the following formula I. The method comprises that: in an inert solvent, in the presence of an alkaline agent, tryptophan and a methylating agent CH3X (X is defined in the specification) are subjected to a reaction, and separation is performed to obtain the desired product 1-methyl tryptophan. According to the present invention, the organic solvent is adopted as the reaction medium, the suitable alkaline reagent is adopted as the dehydrogenating agent, the tryptophan reacts with the methyl halide, and the crude product is subjected to extraction, washing, re-crystallization and other operations so as to obtain the high purity 1-methyl tryptophan; and the method has characteristics of good yield, strong selectivity, simple operation, safety, and easy control. The formula I is defined in the specification.

Total synthesis of (-)-ardeemin

(Chemical Equation Presented) Total synthesis of potent anti-MDR indole alkaloids (-)-ardeemin and its N-acyl analogues has been accomplished from L-tryptophan with about 2% overall yield in 20 steps. The key step depended on the newly developed three-ste