64709-57-5

Basic information

• Product Name: CHLOROACETYL-L-TRYPTOPHAN
• Synonyms: CHLOROACETYL-L-TRYPTOPHAN;CHLOROAC-TRP-OH;CHLOROAC-TRYPTOPHAN;CLAC-TRP-OH;N-CHLOROACETYL-L-TRP;N-CHLOROACETYL-L-TRYPTOPHAN;N-chloroacetyl-L-tryptophan crystalline;chloroacetyltryptophan
• CAS NO: 64709-57-5
• Molecular Formula: C₁₃H₁₃ClN₂O₃
• Molecular Weight: 280.71
• EINECS: 265-029-5
• Product Categories: Amino Acids;Indoles;Tryptophans;A - H;Amino Acids;Modified Amino Acids
• Mol File: 64709-57-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: 610.2 °C at 760 mmHg
• Flash Point: 322.8 °C
• Appearance: /
• Density: 1.428 g/cm³
• Vapor Pressure: 9.66E-16mmHg at 25°C
• Refractive Index: 24 ° (C=2, MeOH)
• Storage Temp.: −20°C
• PKA: 3.22±0.10(Predicted)
• CAS DataBase Reference: CHLOROACETYL-L-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROACETYL-L-TRYPTOPHAN(64709-57-5)
• EPA Substance Registry System: CHLOROACETYL-L-TRYPTOPHAN(64709-57-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64709-57-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 1171, 1958 DOI: 10.1021/jo01102a025

InChI:InChI=1/C13H13ClN2O3/c14-6-12(17)16-11(13(18)19)5-8-7-15-10-4-2-1-3-9(8)10/h1-4,7,11,15H,5-6H2,(H,16,17)(H,18,19)/p-1/t11-/m1/s1

Upstream product

• 79-04-9 chloroacetyl chloride 
• 73-22-3 L-Tryptophan 

Downstream Products

• 5419-44-3 N^α-iodoacetyl-L-tryptophan 
• 141734-67-0 4-(tert-butyldiphenylsiloxymethyl)-1,3,4,5,6,7-hexahydro-6-oxopyrrolo<4,3,2-fg><3>benzazocine 
• 78818-45-8 (S)-2-(2-Benzoylsulfanyl-acetylamino)-3-(1H-indol-3-yl)-propionic acid 
• 108273-71-8 (S)-methyl-2-(2-chloro-acetylamino)-3-(1H-indol-3-yl)propanoate 

Relevant articles and documents

Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation

Bicyclic and tricyclic peptides have emerged as promising candidates for the development of protein binders and new therapeutics. However, convenient and efficient strategies that can generate topologically controlled bicyclic and tricyclic peptide scaffolds from fully-unprotected peptides are still much in demand, particularly for those amenable to the design of biosynthetic libraries. In this work, we report a reliable chemical and ribosomal synthesis of topologically controlled bicyclic and tricyclic peptide scaffolds. Our strategy involves the combination of selenoether cyclization followed by disulfide or thioether cyclization, yielding desirable bicyclic and tricyclic peptides. This work thus lays the foundation for developing peptide libraries with controlled topology of multicyclic scaffolds for in vitro display techniques.

Synthesis of 3,4-Bridged Indoles by Photocyclisation Reactions. Part 1. Photocyclisation of Halogenoacetyl Tryptophan Derivatives

Although irradiation of N-chloroacetyltryptophan results in a poor yield of photocyclisation to the indole 4-position due to competing cyclisation to C-2, the photocyclisation of (dichloroacetyl)tryptophan derivatives gives, after addition of a nucleophile in work-up, 7-substituted pyrrolobenzazocines in good yield and with trans-stereospecificity.N-(Trichloroacetyl)tryptophan derivatives also undergo photocyclisation to give 3,4-bridged indoles.The structures of the azocinoindoles 13, 21, 22 and 35, and the azepinoindole 15 were confirmed by X-ray crystallography.In one case the preparation of a cycloalkaindole was possible by the irradiation of the α-chloro amide of an indol-3-yl alkanoic acid.