35661-40-6Relevant articles and documents
A combined SPS-LCD sensor for screening protease specificity
Birchall, Louise S.,Ulijn, Rein V.,Webb, Simon J.
, p. 2861 - 2863 (2008)
A hydrogel-based sensor for screening protease specificity has been developed that combines the versatility of solid-phase synthesis (SPS) with the simplicity of liquid crystal display (LCD) technology. The Royal Society of Chemistry.
Single Amino-Acid Based Self-Assembled Biomaterials with Potent Antimicrobial Activity
Misra, Souvik,Mukherjee, Soumyajit,Ghosh, Anamika,Singh, Pijush,Mondal, Sanjoy,Ray, Debes,Bhattacharya, Gourav,Ganguly, Debabani,Ghosh, Alok,Aswal,Mahapatra, Ajit K.,Satpati, Biswarup,Nanda, Jayanta
, p. 16744 - 16753 (2021/10/25)
The design and development of soft biomaterials based on amino acid and short-peptide have gained much attention due to their potent biomedical applications. A slight alteration in the side-chain of single amino acid in a peptide or protein sequence has a huge impact on the structure and function. Phenylalanine is one of the most studied amino acids, which contains an aromatic phenyl group connected through a flexible ?CH2? unit. In this work, we have examined whether flexibility and aromatic functionality of phenylalanine (Phe) are important in gel formation of model gelator Fmoc-Phe-OH or not. To examine this hypothesis, we synthesized Fmoc-derivatives of three analogues unnatural amino acids including cyclohexylalanine, phenylglycine, and homophenylalanine; which are slightly varied from Phe. Interestingly, all these three new analogues formed hydrogels in phosphate buffer at pH 7.0 having different gelation efficacy and kinetics. This study suggests that the presence of aromatic side-chain and flexibility are not mandatory for the gelation of this model gelator. Newly synthesized unnatural amino acid derivatives have also exhibited promising antimicrobial activity towards gram-positive bacteria by inhibiting cellular oxygen consumption. We further determined the biocompatibility of these amino acid derivatives by using a hemolysis assay on human blood cells. Overall studies described the development of single amino acid-based new injectable biomaterials with improved antimicrobial activity by the slight alteration in the side-chain of amino acid.
Dicyclohexylurea derivatives of amino acids as dye absorbent organogels and anion sensors
Roy, Karabi,Ghosh, Suvankar,Chetia, Monikha,Satpati, Priyadarshi,Chatterjee, Sunanda
, p. 3026 - 3039 (2019/03/21)
Dicyclohexyl urea (DCU) derivatives of amino acids Fmoc-Phe-DCU (M1), Fmoc-Phg-DCU (M2) and Fmoc-Gaba-DCU (M3) have been shown to form phase selective, thermoreversible and mechanically robust gels in a large range of organic solvents. This is the first report of low molecular weight gelators (LMWG) from DCU derivatives of amino acids. The self-assembly mechanism of the organogels has been probed using concentration dependent 1H NMR, DMSO titration 1H NMR, fluorescence, FTIR, PXRD and FESEM techniques. Self-assembly leading to gelation process is mainly driven by hydrophobicity and π-π stacking interactions in between Fmoc groups. Interestingly, the gels can absorb several kinds of organic dyes efficiently and can be reused for dye absorption for multiple cycles. Additionally, M1-M3 act as sensors for anions like fluoride, acetate and hydroxide, for which they have specific fluorescence response. Gel formation by M1-M3 is completely arrested in the presence of fluoride. The possible binding mode of fluoride has been delineated using DFT studies. Calculations suggest, involvement of urea NH in a six membered intramolecular hydrogen bond, rendering it unavailable for fluoride binding. Backbone -NH of the amino acids of M1-M3 is responsible for fluoride binding. The reported small, economically viable, synthetically facile molecules not only enrich the repertoire of LMWG molecules, but can have multifaceted applications.
