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Upstream product

• 60-18-4 L-tyrosine 
• 112-67-4 n-hexadecanoyl chloride 
• 1080-06-4 L-Tyr-OMe 
• 57-10-3 1-hexadecylcarboxylic acid 
• 214706-38-4 (S)-methyl 3-(4-hydroxyphenyl)-2-(palmitamido)propanoate 
• 14464-31-4 palmitic acid N-succinimide ester 
• 949-67-7 L-tyrosine ethyl ester 
• 58725-51-2 N,O-dipalmitoyl-L-tyrosine 

Relevant academic research and scientific papers

An Ichip-Domesticated Sponge Bacterium Produces an N-Acyltyrosine Bearing an α-Methyl Substituent

The ichip (isolation chip) was employed for the first time in a marine sponge (Xestospongia muta), and a putatively new bacterial species, Alteromonas sp. RKMC-009, was isolated. Strain RKMC-009 produces a novel N-acyltyrosine (1) that is appended with a

N-ACYL-TYROSINE DERIVATIVES AND USES THEREOF

Provided herein are compounds of Formula A, methods for the preparation thereof, and uses thereof for treating or preventing bacterial infections.

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.

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.

Multi-stimuli responsive self-healing metallo-hydrogels: Tuning of the gel recovery property

A series of amphiphilic tyrosine based self-healable, multi-stimuli responsive metallo-hydrogels have been discovered. Formation of these hydrogels is highly selective to Ni2+ ions. The self-healing property and the stiffness of these metallo-hydrogels can be tuned by varying the chain length of the corresponding gelator amphiphile. The Royal Society of Chemistry 2014.

Evaluation of inhibitory actions of flavonols and related substances on lysophospholipase D activity of serum autotaxin by a convenient assay using a chromogenic substrate

Overproduction of lysophosphatidic acid (LPA) by lysophospholipase D/autotaxin (lysoPLD/ATX) is postulated to be involved in the promotion of cancer and atherosclerosis. A lysoPLD inhibitor may be utilized to ameliorate the LPA-related pathological condit

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.

Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation

A series of amide derivatives of long-chain fatty acids has been studied for their effects on the proliferation of cancer cells in vitro. Fatty acids ranged from palmitic to higher polyunsaturated types containing 22 carbon atoms. The amino portions of the molecules included ammonia, ethanolamine, various amino acids and dopamine. Several cell lines were used as models and these included HTB-125 (normal human breast cells), HTB-126 (human breast cancer cells), HeLa (cervical cancer cells), WI-38 (human embryonic lung cells), RAW264.7 (mouse macrophage tumor cells) and RBL-2H3 (rat basophilic leukemia cells). The HTB lines were obtained from the same donor, so, could be considered a matched pair, that is, normal control versus cancer cells and thus, provide a model for testing specificity of action for the acylamido analogs. While many compounds were efficacious in inhibiting the proliferation of various cell lines, only two analogs showed a high degree of specificity in the matched HTB cell lines. N-palmitoyl dopamine and N-palmitoyl tyrosine each demonstrated complete specificity of action at a concentration of 10 μM and were highly efficacious in both cases. No clear structure-activity pattern could be derived from these studies since the intensity of the inhibitory action seemed to depend on three factors, namely, the fatty acid, the amine group and the cell type.

Synthetic libraries of tyrosine-derived bacterial metabolites

The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters were synthesized in solution-phase.

Chiral surfaces in micelles of enantiomeric N-palmitoyl- and N-stearoylserine

Circular dichroism (CD) spectra were recorded with micellar aggregates of a series of N-palmitoyl and N-stearoyl derivatives of amino acid enantiomers. N-Palmitoyl- and N-stearoyl-L- (or -D-) serine in the micelle form (10-4 M in aqueous 0.01 M KOH) exhibited a strong CD band centered at 213-215 nm which could be completely abolished by disintegrating the micelles in 50% ethanol. Analogous CD spectra of enantiomeric N-palmitoyl derivatives of tyrosine or proline did not display any exclusive band for the micellar form. The CD spectra of the enantiomeric N-palmitoyl- or N-stearoylserine micelles presumably originated from a repetitive arrangement of the amide planes on the micellar surface. Computer modeling suggested an alternating tilt of the amide planes associated with the formation of parallel spines of -NH?OC- intermolecular hydrogen bonds which cover the micellar surface. Each of such spines has a supramolecular chirality, which is presumably the origin of the observed CD band. The network of such chiral spines forms a unique chiral surface which may bear important implications for surface recognition and catalysis.