72254-56-9

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Second harmonic optical activity of tryptophan derivatives adsorbed at the air/water interface

Optical activity in second harmonic reflection from the air/water interface of solutions of simple tryptophan (trp) derivatives has been investigated. The derivatives include D- and L-optical isomers of Boc-trp and DD- and LL-isomers of the dipeptide Boc-trp-trp, where Boc is tert-butyloxycarbonyl. An experimental method based on polarization modulation of fundamental radiation by rotation of a quarter-wave retardation plate has been used to completely characterize the second-order nonlinear susceptibilities of the chiral surfaces, for the fundamental wavelength ?? = 564 nm. Boc-trp and Boc-trp-trp show similar chiral contributions to the nonlinear susceptibilities, which indicates that the chiral response does not depend on intramolecular interactions between trp residues. The efficiency of second harmonic reflection has been shown to be resonantly enhanced at the two-photon level, in the region of the near-UV bands (a??280 nm) of the indole chromophore of tryptophan. The origin of the chiral response is discussed in terms of simple microscopic models, and a comparison is made with optical activity of tryptophanyl compounds in linear spectroscopy. The peptide gramicidin, incorporating several trp residues, showed no evidence of optical activity in second harmonic reflection from the air/water interface. This indicates that second harmonic optical activity is sensitive to structural effects such as conformational and orientational distributions of trp residues at the interface.

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.

Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides

We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium sal

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.

MITHRAMYCIN DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY

Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

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.

Catalytic enantioselective acyl transfer: the case for 4-PPY with a C-3 carboxamide peptide auxiliary based on synthesis and modelling studies

A series of 4-pyrrolidinopyridine (4-PPY) C-3 carboxamides containing peptide-based side chains have been synthesised and evaluated in the kinetic resolution of a small library of chiral benzylic secondary alcohols. A key design element was the incorporation of a tryptophan residue in the peptide side chain for promoting π-stacking between peptide side chain and the pyridinium ring of the N-acyl intermediate, in which modelling was used as a structure-based guiding tool. Together, a catalyst containing a LeuTrp-N-Boc side chain (catalyst 8) was identified that achieved s-values up to and in slight excess of 10. A transition-state model based on the modelling is proposed to explain the origin of enantioselectivity. This study establishes the usefulness of modelling as a structure-based guiding tool for enantioselectivity optimization as well as the potential for developing scalable peptide-based DMAP-type catalysts for large-scale resolution work.

Modular incorporation of 1-benzyltryptophan into dipeptide hosts that bind acetylcholine in pure water

Proteins that recognize and bind quaternary ammonium ions depend on " aromatic-cage " structural motifs that use multiple aromatic residues to engage the side chain's ammonium cation. We introduce herein the use of 1-benzyltryp- tophan (Trp(Bn)) residues as synthetic, unnatural partial analogues of natural aromatic cages. We demonstrate the modular incorporation of these building blocks into simple dipeptide hosts and show that they are capable of binding quaternary ammonium ions in buffered water and in chloroform.

Diazonamide studies. A direct synthesis of the indole bis-oxazole fragment from tri- and tetra-peptides using biomimetic oxidative cyclizations

The oxidation of several readily prepared tryptophan containing tri- and tetrapeptides with DDQ results in a biomimetic cyclization and direct formation of the indole bis-oxazole fragment of diazonamide A, establishing that such a transformation is a viab