6159-33-7

Basic information

• Product Name: L-tryptophan monohydrochloride
• Synonyms: L-tryptophan monohydrochloride;Einecs 228-179-2;L-Tryptophan HCl;Tryptophan hydrochloride, L-;Tryptophan hydrochloride,l
• CAS NO: 6159-33-7
• Molecular Formula: C₁₁H₁₂N₂O₂*ClH
• Molecular Weight: 240.68612
• EINECS: 228-179-2
• Mol File: 6159-33-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 447.9°C at 760 mmHg
• Flash Point: 224.7°C
• Appearance: /
• Vapor Pressure: 8.3E-09mmHg at 25°C
• CAS DataBase Reference: L-tryptophan monohydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-tryptophan monohydrochloride(6159-33-7)
• EPA Substance Registry System: L-tryptophan monohydrochloride(6159-33-7)

Safety Data

• Hazardous Substances Data: 6159-33-7(Hazardous Substances Data)

Usage

General Description

L-tryptophan monohydrochloride is a chemical compound that is a salt form of the essential amino acid L-tryptophan. It is commonly used as a dietary supplement and is also an important precursor in the biosynthesis of serotonin and melatonin, which are neurotransmitters that regulate mood and sleep. L-tryptophan monohydrochloride is also known for its role in protein synthesis and has been studied for its potential therapeutic effects in treating conditions such as depression, anxiety, and insomnia. Additionally, L-tryptophan monohydrochloride has been used as a precursor in the production of niacin (vitamin B3) and has found applications in the field of pharmaceuticals and nutrition.

InChI:InChI=1/C11H12N2O2.ClH/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10;/h1-4,6,9,13H,5,12H2,(H,14,15);1H/t9-;/m0./s1

Upstream product

• 73-22-3 L-Tryptophan 
• 20696-57-5 L-tryptophanamide 
• 120-72-9 indole 
• 56-45-1 L-serin 

Downstream Products

• 113391-83-6 methyl N-p-nitrobenzylidenetryptophanate 
• 5022-65-1 L-tryptophanamide hydrochloride 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 91200-21-4 (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate 
• 179799-40-7 C₁₈H₁₇N₃O 
• 27520-72-5 N-formyl-L-tryptophan 
• 35737-15-6 Fmoc-Trp-OH 
• 79815-18-2 methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 42438-90-4 3-carboxy-1,2,3,4-tetrahydro-2-carboline 
• 113370-91-5 methyl 2-indol-3ylmethyl-4-p-nitrophenyl-6,8-dioxo-7-phenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate 
• 4299-70-1 L-tryptophan methyl ester 
• 32675-71-1 N-phthalimide-L-tryptophan 
• 73170-51-1 Z-Glu-Trp 
• 88645-10-7 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxamide 

Relevant articles and documents

LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates

Large neutral amino acid transporter 1 (LAT1) is a solute carrier protein located primarily in the blood–brain barrier (BBB) that offers the potential to deliver drugs to the brain. It is also up-regulated in cancer cells, as part of a tumor's increased metabolic demands. Previously, amino acid prodrugs have been shown to be transported by LAT1. Carboxylic acid bioisosteres may afford prodrugs with an altered physicochemical and pharmacokinetic profile than those derived from natural amino acids, allowing for higher brain or tumor levels of drug and/or lower toxicity. The effect of replacing phenylalanine's carboxylic acid with a tetrazole, acylsulfonamide and hydroxamic acid (HA) bioisostere was examined. Compounds were tested for their ability to be LAT1 substrates using both cis-inhibition and trans-stimulation cell assays. As HA-Phe demonstrated weak substrate activity, its structure–activity relationship (SAR) was further explored by synthesis and testing of HA derivatives of other LAT1 amino acid substrates (i.e., Tyr, Leu, Ile, and Met). The potential for a false positive in the trans-stimulation assay caused by parent amino acid was evaluated by conducting compound stability experiments for both HA-Leu and the corresponding methyl ester derivative. We concluded that HA's are transported by LAT1. In addition, our results lend support to a recent account that amino acid esters are LAT1 substrates, and that hydrogen bonding may be as important as charge for interaction with the transporter binding site.

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.

Method for recovering optically active tryptophan

Optically active tryptophan of high purity can be obtained in high yields from a tryptophan fermentation broth, using crystallization of optically active tryptophan hydrochloride in combination with concurrent neutralization crystallization. According to the present invention, optically active tryptophan from a tryptophan containing fermentation broth, is carried out by (a) removing cells from the fermentation broth, adding hydrochloric acid, or a mixture of hydrochloric acid and an inorganic salt which contains chloride ions, to the cell-free broth to effect crystallization, (b) separating optically active tryptophan hydrochloride, (c) dissolving the optically active tryptophan hydrochloride, and (d) subjecting the resulting solution and an alkali solution to concurrent neutralization crystallization, maintaining a pH of the crystallization solution in the range of from 3 to 8.