65615-90-9

Usage

Chemical Properties

Brown Solid

Upstream product

• 65615-89-6 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate 
• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 540-37-4 p-aminoiodobenzene 
• 67-56-1 methanol 
• 55533-24-9 L-N-tert-butoxycarbonyl-p-aminophenylalanine 
• 63-91-2 L-phenylalanine 
• 106-40-1 4-bromo-aniline 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 

Downstream Products

• 145040-97-7 C₂₄H₃₀N₄O₇S 
• 219496-61-4 (S)-2-tert-butoxycarbonylamino-3-[4-(2,6-dichloro-benzoylamino)-phenyl]-propionic acid methyl ester 
• 643018-84-2 (S)-2-(4-(2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl)phenylamino)benzoic acid 
• 857870-41-8 C₂₂H₂₆IN₃O₅ 
• 1191036-87-9 (S)-methyl 3-(4-(3-allylureido)phenyl)-2-(tert-butoxycarbonylamino)propanoate 
• 220846-30-0 (S)-2-(2-Bromo-5-methoxy-benzoylamino)-3-[4-(2,6-dichloro-benzoylamino)-phenyl]-propionic acid methyl ester 
• 220848-32-8 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(2-(1-methyl)ethyl-6-methylphenyl)carbonyl]-L-phenylalanine methyl ester 
• 220848-35-1 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(2-ethyl-6-methylphenyl)carbonyl]-L-phenylalanine methyl ester 
• 501084-85-1 (S)-3-[4-(2,6-Dichloro-benzoylamino)-phenyl]-2-(2,6-difluoro-benzoylamino)-propionic acid methyl ester 
• 1609192-58-6 (S)-methyl 3-(4-(benzylthio)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 220848-29-3 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(2-chloro4-hydroxyphenyl)carbonyl]-L-phenylalanine methyl ester 
• 220848-31-7 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(2-methylsulfonylphenyl)carbonyl]-L-phenylalanine methyl ester 

Relevant academic research and scientific papers

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

Photoswitchable CENP-E Inhibitor Enabling the Dynamic Control of Chromosome Movement and Mitotic Progression

Interfering with mitosis is a potential cancer therapy strategy. However, the lack of controllability of antimitotic drugs in cell growth suppression causes severe side effects and limits their clinical utility. Herein, we developed an azobenzene-based ph

Tyrosine–chlorambucil conjugates facilitate cellular uptake through L-type amino acid transporter 1 (LAT1) in human breast cancer cell line MCF-7

l-type amino acid transporter 1 (LAT1) is an amino acid transporter that is overexpressed in several types of cancer and, thus, it can be a potential target for chemotherapy. The objectives of this study were to (a) synthesize LAT1-targeted chlorambucil d

An Optically Active Polymer for Broad-Spectrum Enantiomeric Recognition of Chiral Acids

Recognition of enantiomers of chiral acids by anion–π or lone pair–π interactions has not yet been investigated but is a significant and attractive challenge. This study reports an optically active polymer-based supramolecular system with capabilities of discriminating enantiomers of various chiral acids. The polymer featuring alternate π-acidic naphthalenediimides (NDIs) and methyl l-phenylalaninates in the backbone exhibits an unprecedented slow self-assembly process that is susceptible to perturbation by various chiral acids. Thus, the combination of anion–π or lone pair–π interactions and sensitivity of the polymeric self-assembly process to external chiral species endows the system with recognition capabilities. This is the first time that anion–π or lone pair–π interactions have been applied in the recognition of enantiomers of various chiral acids with a single system. The results shed light on new strategies for material design by integrating π-acidic aromatic systems and chiral building blocks to afford relevant advanced functions.

Supramolecular self-assembly of chiral polyimides driven by repeat units and end groups

Pyromellitic diimides (PMDIs) are effective building blocks for the construction of supramolecular systems but are infrequently used in comparison with other electron-deficient aromatic systems. We report PMDI-based chiral polyimides that form polymeric supramolecular systems with unique self-assembly features that show time-dependent spectroscopic behaviour. Extensive investigations revealed the driving forces for the self-assembly of the polyimides. One is the complementary aromatic π-π stacking between electron-accepting PMDI and electron-donating phenyl ring in the polymer backbones, and another is the hydrogen bonding interactions of the end groups. The self-assembly is readily disrupted by guest molecules with strong associations with the PMDI and the end groups. The introduction of flexible arylether diimides into the PMDI-based copolymer backbones and the sequence of PMDIs and arylether diimides in the copolymer backbones significantly influence the self-assembly of the polyimides. The results elucidate the mechanisms of polymeric self-assembly of chiral polyimides, providing important information for the development of materials based on polymeric supramolecular systems with properties and functions regulated by composition, sequence and end groups.

Tubulysin compounds, methods of making and use

Tubulysin compounds of the formula (I) where R1, R2, R3a, R3b, R4, R5, W, and n are as defined herein, are anti-mitotic agents that can be used in the treatment of cancer, especially when conjugated to a targeting moiety.

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1)

L-Type amino acid transporter 1 (LAT1) is a transmembrane protein expressed abundantly at the blood-brain barrier (BBB), where it ensures the transport of hydrophobic acids from the blood to the brain. Due to its unique substrate specificity and high expression at the BBB, LAT1 is an intriguing target for carrier- mediated transport of drugs into the brain. In this study, a comparative molecular field analysis (CoMFA) model with considerable statistical quality (Q2=0.53, R2=0.75, Q2 SE=0.77, R2 SE=0.57) and good external predictivity (CCC=0.91) was generated. The model was used to guide the synthesis of eight new prodrugs whose affinity for LAT1 was tested by using an in situ rat brain perfusion technique. This resulted in the creation of a novel LAT1 prodrug with l-tryptophan as the promoiety; it also provided a better understanding of the molecular features of LAT1-targeted high-affinity prodrugs, as well as their promoiety and parent drug. The results obtained will be beneficial in the rational design of novel LAT1-binding prodrugs and other compounds that bind to LAT1.

Photoresponsive supramolecular architectures based on polypeptide hybrids

Self-aggregation has recently emerged as an efficient tool for the production of well-ordered supramolecular structures at the nanometric scale. In this framework, peptides offer important advantages as building blocks because of their biocompatibility and 3D-structural/functional diversities. The chemical diversity of peptides may be further expanded by use of noncoded amino acids. In the present work, we focused our attention on two known photoswitchable azobenzene-containing α-amino acids and used them as initiators for the reversible modulation of the cis/trans conformational states of two poly(γ-benzyl-l-glutamate)-based hybrid molecules with either C2 or C3 symmetry. The microscopic photoresponsive self-assembly of these compounds was examined in detail. Moreover, these hybrids were exploited in the construction of macroscopic supramolecular architectures via the electrospinning technique. Finally, after appropriate thiol functionalization, we fabricated and characterized dimeric and trimeric gold nanoparticle/polypeptide hybrid systems.

Tryptophan-based fluorophores for studying protein conformational changes

With the continuing interest in deciphering the interplay between protein function and conformational changes, small fluorescence probes will be especially useful for tracking changes in the crowded protein interior space. Presently, we describe the poten

Lipid Compounds Targeting VLA-4

The invention relates to the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein n, G, W, X, Y, and R1 are defined in the detailed description and claims. The compounds of formula I bind to or associate with VLA-4 and can be used in delivery formulations to deliver drugs, nucleic acids, or other therapeutic compounds to tissues or cells expressing VLA-4.