80546-83-4

Upstream product

• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 186581-53-3 diazomethane 
• 13122-89-9 (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate 
• 88224-00-4 L-phenylalanine allyl ester p-toluenesulfonic acid salt 
• 4892-10-8 N-(benzyloxycarbonyl)-L-phenylalanyl-L-phenylalanine methyl ester 
• 15215-74-4 methyl (tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalaninate 
• 21685-51-8 D-phenylalanine methyl ester 
• 13122-87-7 Cbz-Phe-D-Phe-OMe 

Downstream Products

• 1032171-42-8 C₅₉H₇₆N₂O₉S 
• 1323358-01-5 C₂₅H₂₆N₆O₅ 
• 1383732-37-3 cinnamoyl-Phe-Phe-H 
• 17528-19-7 N-alpha-carbobenzoxy-L-phenylalanyl-L-phenylalanyl-L-phenylalanine methyl ester 
• 17528-17-5 L-phenylalanyl-L-phenyalanyl-L-phenylalnine methyl ester 

Relevant academic research and scientific papers

Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies

Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o

Crystal structure and supramolecular arrangement of heterochiral tripeptides

The self-assembly properties of all possible stereoisomers of terminally protected Boc-Val-Phe-Phe-OMe, having sequence homogeneity with Alzheimer's amyloid-beta (Aβ18-20) peptide was investigated. The morphology analysis by field emission scan

Photo-Controllable Catalysis and Chiral Monosaccharide Recognition Induced by Cyclodextrin Derivatives

A supramolecular catalytic system was constructed from polycationic α-cyclodextrin (6-Iz-α-CD) and gold nanoparticles (AuNP) using a supramolecular assembly strategy. The cavity of cyclodextrin is the channel by which the substrate molecules come into con

Chloride-Assisted Peptide Macrocyclization

The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtai

Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers

The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Al

Mithramycin 2′-Oximes with Improved Selectivity, Pharmacokinetics, and Ewing Sarcoma Antitumor Efficacy

Mithramycin A (MTM) inhibits the oncogenic transcription factor EWS-FLI1 in Ewing sarcoma, but poor pharmacokinetics (PK) and toxicity limit its clinical use. To address this limitation, we report an efficient MTM 2′-oxime (MTMox) conjugation strategy for rapid MTM diversification. Comparative cytotoxicity assays of 41 MTMox analogues using E-twenty-six (ETS) fusion-dependent and ETS fusion-independent cancer cell lines revealed improved ETS fusion-independent/dependent selectivity indices for select 2′-conjugated analogues as compared to MTM. Luciferase-based reporter assays demonstrated target engagement at low nM concentrations, and molecular assays revealed that analogues inhibit the transcriptional activity of EWS-FLI1. These in vitro screens identified MTMox32E (a Phe-Trp dipeptide-based 2′-conjugate) for in vivo testing. Relative to MTM, MTMox32E displayed an 11-fold increase in plasma exposure and improved efficacy in an Ewing sarcoma xenograft. Importantly, these studies are the first to point to simple C3 aliphatic side-chain modification of MTM as an effective strategy to improve PK.

Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct

A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(l-tyrosyl-l-tyrosine) results in sub-μM binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme FeIII. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.

Pure organic amino acid derivative for room-temperature phosphorescence emission, preparation method thereof and organic luminescent material

The invention provides a pure organic amino acid derivative for room-temperature phosphorescence emission and a preparation method thereof. The pure organic amino acid derivative for room-temperaturephosphorescence emission has a structure as shown in a formula (I). The pure organic amino acid derivatives for room-temperature phosphorescence emission are obtained by combining various pure organicphosphorescence monomers with an amino acid derivative, the reaction raw materials are easy to obtain, the reaction process is simple, the product is non-toxic and harmless, and the defects of complex preparation of crystalline organic room-temperature phosphorescence materials and the like are overcome.

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.