112525-72-1

Basic information

• Product Name: N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN
• Synonyms: N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN;Boc-DL-tryptophan;N-(tert-Butoxycarbonyl)-DL-tryptophan;N-α-Boc-DL-Tryptophan
• CAS NO: 112525-72-1
• Molecular Formula: C₁₆H₂₀N₂O₄
• Molecular Weight: 304.34
• Mol File: 112525-72-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 131 °C(dec.)
• Boiling Point: 535.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.262±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.00±0.10(Predicted)
• CAS DataBase Reference: N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN(112525-72-1)
• EPA Substance Registry System: N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN(112525-72-1)

Safety Data

• Hazardous Substances Data: 112525-72-1(Hazardous Substances Data)

Usage

General Description

N-Tert-Butoxycarbonyl-DL-Tryptophan, also known as Boc-DL-Trp-Oh, is a chemical compound often utilized in scientific research, specifically in peptide and protein synthesis. It is a derivative of the essential amino acid tryptophan, which is crucial in protein synthesis within the body and precursor to neurotransmitters like serotonin and melatonin. The N-Tert-Butoxycarbonyl element, Boc for short, is a protective group used in organic chemistry to prevent certain reactions from occurring prematurely. Boc-DL-Trp-Oh is typically synthesized in a laboratory setting and provides a crucial component in various biochemical studies.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 54-12-6 Trp 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15142-91-3 rac-3-(1H-indol-3-yl)-2-methylpropanoic acid 
• 141215-69-2 N-(tert-butyloxycarbonyl)-2-(3-indolyl)glycin methyl ester 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 

Downstream Products

• 170568-11-3 2-t-butoxycarbonylamino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-propanamide 
• 174225-57-1 (RS)-N-(2-chlorobenzyl)-2,5-dioxo-3-(1H-indol-3-ylmethyl)piperazine 
• 183008-66-4 2-t-butoxycarbonylamino-3-(1H-indol-3-yl)-N-(2-chlorobenzyl)-propanamide 
• 156814-61-8 5-(3,5-Bistrifluoromethylphenyl)-2-t-butyloxycarbonylamino-1-(3-indolyl)-4-penten-3-one 

Relevant articles and documents

Development of Small-Molecules Targeting Receptor Activator of Nuclear Factor-κB Ligand (RANKL) - Receptor Activator of Nuclear Factor-κB (RANK) Protein-Protein Interaction by Structure-Based Virtual Screening and Hit Optimization

Targeting RANKL/RANK offers the possibility of developing novel therapeutic approaches to treat bone metabolic diseases. Multiple efforts have been made to inhibit RANKL. For example, marketed monoclonal antibody drug Denosumab could inhibit the maturation of osteoclasts by binding to RANKL. This study is an original approach aimed at discovering small-molecule inhibitors impeding RANKL/RANK protein interaction. We identified compound 34 as a potent and selective RANKL/RANK inhibitor by performing structure-based virtual screening and hit optimization. Disruption of the RANKL/RANK interaction by 34 effectively inhibits RANKL-induced osteoclastogenesis and bone resorption. The expression of osteoclast marker genes was also suppressed by treatment of 34. Furthermore, 34 markedly blocked the NFATc1/c-fos pathway. Thus, our current work demonstrates that the chemical tractability of the difficult PPI (RANKL/RANK) target by a small-molecule compound 34 offers a potential lead compound to facilitate the development of new medications for bone-related diseases.

t-Butyl Benzotriazol-1-yl Carbonate. A New Efficient Reagent for t-Butoxycarbonylation of Amino Acids

t-Butyl benzotriazol-1-yl carbonate, a stable crystalline compound, is found to be exceedingly effective in the t-butoxycarbonylation of amino acids.

Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease

A combination of tacrine and tryptophan led to the development of a new family of heterodimers as multi-target agents with potential to treat Alzheimer's disease. Based on the in vitro biological profile, compound S-K1035 was found to be the most potent inhibitor of human acetylcholinesterase (hAChE) and human butyrylcholinesterase (hBChE), demonstrating balanced IC50 values of 6.3 and 9.1 nM, respectively. For all the tacrine-tryptophan heterodimers, favorable inhibitory effect on hAChE as well as on hBChE was coined to the optimal spacer length ranging from five to eight carbon atoms between these two pharmacophores. S-K1035 also showed good ability to inhibit Aβ42 self-aggregation (58.6 ± 5.1% at 50 μM) as well as hAChE-induced Aβ40 aggregation (48.3 ± 6.3% at 100 μM). The X-ray crystallographic analysis of TcAChE in complex with S-K1035 pinpointed the utility of the hybridization strategy applied and the structures determined with the two K1035 enantiomers in complex with hBChE could explain the higher inhibition potency of S-K1035. Other in vitro evaluations predicted the ability of S-K1035 to cross blood-brain barrier and to exert a moderate inhibition potency against neuronal nitric oxide synthase. Based on the initial promising biochemical data and a safer in vivo toxicity compared to tacrine, S-K1035 was administered to scopolamine-treated rats being able to dose-dependently revert amnesia.

A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids

Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.