81912-47-2

Upstream product

• 21685-51-8 D-phenylalanine methyl ester 
• 57-10-3 1-hexadecylcarboxylic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 112-67-4 n-hexadecanoyl chloride 
• 67-56-1 methanol 
• 63-91-2 L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 81912-43-8 rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione 
• 74058-64-3 1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 

Downstream Products

• 56217-81-3 N-n-hexadecanoyl (L)-phenylalanine 
• 1147761-30-5 C₃₀H₅₀N₂O₄ 
• 1147761-38-3 C₃₆H₅₁N₃O₄ 

Relevant academic research and scientific papers

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.

In situ formation of AuNPs using fatty N-acylamino hydrazide organogelators as templates

This work reports, for the first time, the synthesis of new fatty N-acylamino hydrazides and demonstrates the activity of these compounds as low-molecular-weight organic gelators and templates for preparation of gold nanoparticles (AuNPs). Initially, we evaluated the gelation properties of fatty N-acylamino hydrazides in various nonpolar and polar solvents (n-hexane, toluene, benzene, cyclohexane, and ethanol). Fatty N-acylamino hydrazide derived of the glycine and stearic acid (C18:0) did not form gels in any of the tested solvents. All other hydrazides did form gels in at least two of the organic solvents tested. The morphology of each gel was observed via scanning electron microscopy. The organogels derived from alanine, valine, and phenylalanine had translucid properties, while the serine organogels were opaque. Afterwards, the synthesis of AuNPs in the presence of the organogelator using microwave irradiation was realized. Organogelator agents reduced HAuCl4 showing plasmon band peaks between 530 and 543 nm. In addition, the method does not require a reducing agent, which is typically a potential source of contamination and toxicity. Therefore, this work confirms the importance of the hydrazide group of the new fatty N-acylamino hydrazides in gel formation and as organogelator agents for preparation of AuNPs.

IMMUNOSTIMULATING AGENT

The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an

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.

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.

Superior SWNT dispersion by amino acid based amphiphiles: Designing biocompatible cationic nanohybrids

Stable aqueous SWNT dispersion up to 92% was achieved using amino acid based amphiphiles through a structure-property investigation. The nanohybrids showed remarkable serum stability and biocompatibility to mammalian cells.

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.

A NEW DETERMINATION OF THE ABSOLUTE CONFIGURATION OF THE CHIRAL AMINE

A new method for assignment of the absolute configuration of the asymmetric carbon atom attached to an amino or imino group using rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione (rac.-HDMTT) (4) is described.

A NEW CHIRAL RECOGNITION IN AMINOLYSIS OF 3-ACYL-4(R)-METHOXYCARBONYL-1,3-THIAZOLIDINE-2-THIONE WITH RACEMIC AMINES

A chiral recognition was observed in aminolysis of 3-acyl-4(R)-methoxycarbonyl-1,3-thiazolidine-2-thione 1 by racemic amine 2 to give an optically active amide (S-excess) and amine (R-excess).