37571-96-3

Usage

Uses

suzuki reaction

InChI:InChI=1/C25H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-24(27)26-23(25(28)29)21-22-18-15-14-16-19-22/h14-16,18-19,23H,2-13,17,20-21H2,1H3,(H,26,27)(H,28,29)/t23-/m0/s1

Upstream product

• 1492-30-4 4-nitrophenyl palmitate 
• 63-91-2 L-phenylalanine 
• 81912-43-8 rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione 
• 75531-13-4 p-Nitrophenyl N-hexadecanoyl-L-phenylalaninate 
• 81912-47-2 N-n-hexadecanoyl methyl (L)-phenylalaninate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 112-67-4 n-hexadecanoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 14464-31-4 palmitic acid N-succinimide ester 
• 75531-09-8 p-nitrophenyl N-hexadecanoyl-D-alanate 
• 75531-09-8 p-nitrophenyl N-hexadecanoyl-L-alanate 

Downstream Products

• 1147761-30-5 C₃₀H₅₀N₂O₄ 
• 1147761-38-3 C₃₆H₅₁N₃O₄ 
• 1351017-43-0 C₃₇H₆₂N₂O₁₂ 
• 1351017-35-0 N-propargyl (N'-palmitoylphenylalanine) amide 

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.

HUMAN MICROBIOTA DERIVED N-ACYL AMIDES FOR THE TREATMENT OF HUMAN DISEASE

The present invention provides compositions and methods for the modulation of G protein-coupled receptors (GPCRs). The invention provides a genetically engineered cell, wherein the cell expresses a human microbial N-acyl synthase (hm-NAS) gene. In one embodiment, the hm-NAS gene is N-acyl serinol synthase. The invention provides a probiotic composition, the probiotic composition comprises a genetically engineered cell of the invention. The invention provides a method for modulating a G protein-coupled receptor (GPCR) activity in a subject, the method comprises administering to the subject an effective amount of a composition comprising at least one selected from the group consisting of a genetically engineered cell, an hm-NAS gene, and a N-acyl amide.

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.

Hydrophobic End-Modulated Amino-Acid-Based Neutral Hydrogelators: Structure-Specific Inclusion of Carbon Nanomaterials

Hydrophobic end-modulated l-phenylalanine-containing triethylene glycol monomethyl ether tagged neutral hydrogelators (1-4) are developed. Investigations determine the gelators' structure-dependent inclusion of carbon nanomaterials (CNMs) in the self-assembled fibrillar network (SAFIN). The gelators (1, 3, and 4) can immobilize water and aqueous buffer (pH3-7) with a minimum gelator concentration of 10-15mg mL-1. The hydrophobic parts of the gelators are varied from a long chain (C-16) to an extended aromatic pyrenyl moiety, and their abilities to integrate 1 D and 2 D allotropes of carbon (i.e., single-walled carbon nanotubes (SWNTs) and graphene oxide (GO), respectively) within the gel are investigated. Gelator1, containing a long alkyl chain (C-16), can include SWNTs, whereas the pyrene-containing 4 can include both SWNTs and GO. Gelator3 fails to incorporate SWNTs or GO owing to its slow rate of gelation and possibly a mismatch between the aggregated structure and CNMs. The involvement of various forces in self-aggregated gelation and physicochemical changes occurring through CNM inclusion are examined by spectroscopic and microscopic techniques. The distinctive pattern of self-assembly of gelators1 and 4 through J- and H-type aggregation might facilitate the structure-specific CNM inclusion. Inclusion of SWNTs/GO within the hydrogel matrix results in a reinforcement in mechanical stiffness of the composites compared with that of the native hydrogels.

Improvements in or Relating to Organic Compounds

A stock solution comprising a compound of formula (I) Wherein R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

Gold nanorod@Chiral mesoporous silica core-shell nanoparticles with unique optical properties

The design and fabrication of chiral nanostructures is a promising approach to realize enantiomeric recognition and separation. In our work, gold nanorod@chiral mesoporous silica core-shell nanoparticles (GNR@CMS NPs) have been successfully synthesized. T

The striking influence of SWNT-COOH on self-assembled gelation

A miniscule amount of f-SWNTs remarkably improved (～17-fold) the gelation efficiency of amphiphilic molecules by triggering the formation of interconnecting self-assembled fibrillar networks (SAFIN) in supramolecular gelation.

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.