72254-56-9

Basic information

• Product Name: methyl N-(tert-butoxycarbonyl)tryptophyltryptophanate
• CAS NO: 72254-56-9
• Molecular Formula: C₂₈H₃₂N₄O₅
• Molecular Weight: 504.5775
• Mol File: 72254-56-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 791.3°C at 760 mmHg
• Flash Point: 432.4°C
• Density: 1.276g/cm³
• Vapor Pressure: 5.08E-25mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: methyl N-(tert-butoxycarbonyl)tryptophyltryptophanate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(tert-butoxycarbonyl)tryptophyltryptophanate(72254-56-9)
• EPA Substance Registry System: methyl N-(tert-butoxycarbonyl)tryptophyltryptophanate(72254-56-9)

Safety Data

• Hazardous Substances Data: 72254-56-9(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 13139-14-5 Boc-Trp-OH 
• 73-22-3 L-Tryptophan 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 852998-99-3 C₇H₁₆NO₂⁽¹⁺⁾*C₂₈H₃₂N₄O₅*Cl^(1-) 
• 4299-70-1 L-tryptophan methyl ester 

Downstream Products

• 20829-55-4 (3S,6S)-3,6-Bis-(1H-indol-3-ylmethyl)-piperazine-2,5-dione 

Relevant articles and documents

A synthetic ditryptophan conjugate that rescues bacteria from mercury toxicity through complexation

The synthesis of ditryptophan-pyridine conjugates and their binding to mercury ions is described. Conjugate 3 shows an excellent ability to sequester mercury from solution and rescue bacterial growth in a concentration-dependent survival assay. It is proposed that such compounds, composed primarily of bioessential/biodegradable components, could be potentially used as sequestrating agents for the removal of Hg(II) ions in detoxification strategies.

Biomimetic approaches to diazonamide A. Direct synthesis of the indole bis-oxazole fragment by oxidation of a TyrValTrpTrp tetrapeptide

Oxidation of a protected TyrValTrpTrp tetrapeptide results in direct formation of the indole bis-oxazole core of diazonamide A. The Royal Society of Chemistry 2006.

A novel molecular scaffold resensitizes multidrug-resistant S. aureus to fluoroquinolones

Nosocomial infections arising from opportunistic pathogens, such as Staphylococcus aureus, are growing unabated, compounded by the rapid emergence of antimicrobial resistance. Herein, we demonstrate a new molecular design that exhibits excellent activity against multidrug-resistant S. aureus with no cytotoxicity and resensitizes fluoroquinolones (FQ) towards FQ-resistant methicillin-resistant S. aureus strains, with DNA gyrase B as the likely molecular target as determined by molecular dynamics (MD) simulations.

Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers

Mithramycin A (1) was identified as the top potential inhibitor of the aberrant ETS transcription factor EWS-FLI1, which causes Ewing sarcoma. Unfortunately, 1 has a narrow therapeutic window, compelling us to seek less toxic and more selective analogues. Here, we used MTMSA (2) to generate analogues via peptide coupling and fragment-based drug development strategies. Cytotoxicity assays in ETS and non-ETS dependent cell lines identified two dipeptide analogues, 60 and 61, with 19.1- and 15.6-fold selectivity, respectively, compared to 1.5-fold for 1. Importantly, the cytotoxicity of 60 and 61 is 100 nM in ETS cells. Molecular assays demonstrated the inhibitory capacity of these analogues against EWS-FLI1 mediated transcription in Ewing sarcoma. Structural analysis shows that positioning the tryptophan residue in a distal position improves selectivity, presumably via interaction with the ETS transcription factor. Thus, these analogues may present new ways to target transcription factors for clinical use.