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suzuki reaction

Upstream product

• 63-91-2 L-phenylalanine 
• 112-76-5 Stearoyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 57-11-4 stearic acid 
• 122889-27-4 N-n-dodecanoyl methyl (L)-phenylalaninate 
• 14464-32-5 stearic acid N-hydroxysuccinimide ester 
• 150-30-1 Phenylalanine 

Relevant academic research and scientific papers

CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF

Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

In search of bioinspired hydrogels from amphiphilic peptides: A template for nanoparticle stabilization for the sustained release of anticancer drugs

The development of potent stimuli-responsive hydrogels has rapidly expanded in the last decades due to their diversified applications in the field of biomedicines. In accordance with this drift, herein, we aimed at modulating a series of amphiphilic peptide analogues with the general formula Me-(CH2)14-CO-NH-CH(X)-COOH, where X = CH2Ph in hydrogelators I (l-Phe) and II (d-Phe) and X = CH2Ph(OH) in hydrogelator III (l-Tyr), which displayed an excellent propensity to immobilize water at room temperature with a minimum gelation concentration of 0.04%/0.05%/0.02% w/v for hydrogelators I-III, respectively, regardless of their configuration at the C-terminal centre. To validate this threshold concentration difference, we performed computational analysis that demonstrated the ability of the side-chains of hydrogelators I and III to remain highly planar with the methylene units of the amphiphile and aromatic rings, promoting favourable correspondence through van der Waals forces and pi-pi stacking. Consequently hydrogelators I and III self-assembled in an ordered organisation superior to hydrogelator II. Furthermore, the spectroscopic and microscopic experiments revealed that the hydrogelators manifested a β-sheet conformation and nanofibrous morphology at the supramolecular level. As observed visually and additionally confirmed by differential scanning calorimetry (DSC) and rheological measurements, the hydrogels exhibited thermo-reversibility, injectability and high mechanical strength. Importantly, these biomaterials were also found to be resistant towards proteolytic degradation and non-cytotoxic in the cell line HEK 293 using a dose-dependant cell viability assay. To date, the development of a structured approach for the release of drugs in a predictable manner from an optimised formulation, using peptide-based hydrogel nanoparticles as a delivery system remains in its infancy. Hence, we developed hydrogel nanoparticles (HNPs) with our fabricated amphiphilic peptides that exploited the weak noncovalent interactions for their fabrication, unlike other cross-linked polymers that require strong covalent or ionic bonds for their formation. Interestingly, the as-synthesized nanoparticles showed an unprecedented ability to release the anticancer drugs 5-fluoro uracil/doxorubicin at physiological conditions depending on the physico-chemical parameters of the drugs. We believe that the reported injectable, biocompatible, amphiphilic peptide-based hydrogels hold future promise as a potential tool to transport drugs to a targeted site at a greater concentration, thus relieving the patient from surgical injury and simultaneously aiding in a faster recovery.

Designed Negative Feedback from Transiently Formed Catalytic Nanostructures

Highly dynamic and complex systems of microtubules undergo a substrate-induced change of conformation that leads to polymerization. Owing to the augmented catalytic potential at the polymerized state, rapid hydrolysis of the substrate is observed, leading to catastrophe, thus realizing the out-of-equilibrium state. A simple synthetic mimic of these dynamic natural systems is presented, where similar substrate induced conformational change is observed and a transient helical morphology is accessed. Further, augmented catalytic potential of these helical nanostructures leads to rapid hydrolysis of the substrate providing negative feedback on the stability of the nanostructures and realization of an out-of-equilibrium state. This simple system, made from amino acid functionalized lipids, demonstrates a substrate-induced self-assembled state, where the fuel-to-waste conversion leads to the temporal presence of helical nanostructures.

Chemically Fueled Dissipative Self-Assembly that Exploits Cooperative Catalysis

In living systems, dissipative processes are driven by the endergonic hydrolysis of chemical fuels such as nucleoside triphosphates. Now, through a simple model system, a transient self-assembled state is realized by utilizing the catalytic effect of histidine on the formation and breaking of ester bonds. First, histidine facilitates the ester bond formation, which then rapidly co-assembles to form a self-supporting gel. An out-of-equilibrium state is realized owing to the cooperative catalysis by the proximal histidines in the assembled state, driving the second pathway and resulting in disassembly to sol. Cooperative effects that use the dual role of imidazoles as nucleophile and as proton donor is utilized to achieve transient assemblies. This simple system mimics the structural journey seen in microtubule formation where the substrate GTP facilitates the non-covalent assembly and triggers a cooperative catalytic process, leading to substrate hydrolysis and subsequent disassembly.

Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration

N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.

METHODS FOR IDENTIFICATION, ASSESSMENT, PREVENTION, AND TREATMENT OF METABOLIC DISORDERS USING PM20D1 AND N-LIPIDATED AMINO ACIDS

The present invention relates to methods for identifying, assessing, preventing, and treating metabolic disorders and modulating metabolic processes using PM20D1 and N- lipidated amino acids.

Self-assembly of azobenzene-based two-component gels

An azobenzene derivative was found to form a two-component gelator with lauroyl or stearoyl phenylalanine although phenylalanine units failed to gel the solvent. During gelation, the yellow sols turned into red gels, implying a sharp color change in the system. In gel, molecules self-assembled into one-dimensional nanofibers. Circular dichroism spectral results indicated that the chirality of phenylalanine was passed on to the azobenzene moiety, which formed a right-handed helical stacking in the gel phase. UV-vis experiments and NMR spectra revealed that the azobenzene derivative and lauroyl phenylalanine formed a complex with a ratio of 1:4. The critical gelation concentrations and gel-to-sol phase transition temperatures were dependent on the ratio of the two compounds. Moreover, the response of two-component gels to mechanical stimulus could result in a gel-to-sol transition. The gels can again self-heal after resting, which is a process that can be reversed numerous times. This journal is

New N-acylamino acids and derivatives from renewable fatty acids: Gelation of hydrocarbons and thermal properties

This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of l-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of l-serine in forming good gels.

Synthesis of lipoamino acids and their activity against cerebral ischemic injury

A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1-10 M.

Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

A variety of fatty acid amides of different naturally occurring l-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them l-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed.