2-Amino-2-thiazoline. VII. Unequivocal structure assignment of the products of the reaction of 2-amino-2-thiazoline and its analogs with carbethoxy isothiocyanate

Klayman, Daniel L.; Woods, Thomas S.

doi:10.1021/jo00927a007

Cited by 32 publications

(3 citation statements)

References 12 publications

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“…Thus, we conclude that the main driving force for recognition is not charge complementation, but rather, a more subtle hydrogen-bond donor−acceptor pattern recognition between largely neutral species in competing aqueous solvent. Moreover, this interaction is sufficiently strong to overcome hydration repulsion forces − between membranes to induce both spatially selective surface adhesion and membrane merger. The biophysics of this binding interaction in water, as well as the range of aqueous-phase assembly chemistry that may be mediated by cyanurate and melamine groups, remains an intriguing topic with potential relevance to the development of new functional materials.…”

Section: Discussionmentioning

confidence: 99%

Lipid Membrane Adhesion and Fusion Driven by Designed, Minimally Multivalent Hydrogen-Bonding Lipids

Gong

Bong

2009

J. Am. Chem. Soc.

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Cyanuric acid (CA) and melamine (M) functionalized lipids can form membranes that exhibit robust hydrogen-bond driven surface recognition in water, facilitated by multivalent surface clustering of recognition groups and variable hydration at the lipid-water interface. Here we describe a minimal lipid recognition cluster: three CA or M recognition groups are forced into proximity by covalent attachment to a single lipid headgroup. This trivalent lipid system guides recognition at the lipid-water interface using cyanurate-melamine hydrogen bonding when incorporated at 0.1-5 mol percent in fluid phospholipid membranes, inducing both vesicle-vesicle binding and membrane fusion. Fusion was accelerated when the antimicrobial peptide magainin was used to anchor trivalent recognition, or when added exogenously to a preassembled lipid vesicle complex, underscoring the importance of coupling recognition with membrane disruption in membrane fusion. Membrane apposition and fusion were studied in vesicle suspensions using light scattering, FRET assays for lipid mixing, surface plasmon resonance, and cryo-electron microscopy. Recognition was found to be highly spatially selective as judged by vesicular adhesion to surface patterned supported lipid bilayers (SLBs). Fusion to SLBs was also readily observed by fluorescence microscopy. Together, these studies indicate effective and functional recognition of trivalent phospholipids, despite low mole percentage concentration, solvent competition for hydrogen bond donor/acceptor sites, and simplicity of structure. This novel designed molecular recognition motif may be useful for directing aqueous-phase assembly and biomolecular interactions.

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Section: Discussionmentioning

confidence: 99%

Lipid Membrane Adhesion and Fusion Driven by Designed, Minimally Multivalent Hydrogen-Bonding Lipids

Gong

Bong

2009

J. Am. Chem. Soc.

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“…We synthesized 1-(2-mercaptoethyl)-1,3,5-triazinane-2,4,6-trione (MTT), a kind of thiol-functionalized CA derivative, and prepared the MTT-stabilized gold nanoparticles (12 nm) by ligand-exchange reaction using MTT and citrate-stabilized Au nanoparticles. Initially, the MTT-stabilized gold nanoparticles were well dispersed in distilled water, and the color of the uniform colloid was wine red due to its strong surface plasmon resonance (SPR) at 519 nm (see Supporting Information).…”

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confidence: 99%

Hydrogen-Bonding Recognition-Induced Color Change of Gold Nanoparticles for Visual Detection of Melamine in Raw Milk and Infant Formula

2009

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The color change induced by triple hydrogen-bonding recognition between melamine and a cyanuric acid derivative grafted on the surface of gold nanoparticles can be used for reliable detection of melamine. Since such a color change can be readily seen by the naked eye, the method enables on-site and real-time detection of melamine in raw milk and infant formula even at a concentration as low as 2.5 ppb without the aid of any advanced instruments.

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“…Deionized water (18 M cm) was obtained from a Millipore Milli-Q Plus 185 water purification system. 1-(2-mercaptoethyl)-1,2,3,4,5,6-hexanhydro-s-triazine-2,4,6-trione (MTT) was synthesized according to the literature [17].…”

Section: Reagentsmentioning

confidence: 99%

Functionalized Au-Fe3O4 nanocomposites as a magnetic and colorimetric bimodal sensor for melamine

Shen

Yang

Zhang

et al. 2016

Sensors and Actuators B: Chemical

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2-Amino-2-thiazoline. VII. Unequivocal structure assignment of the products of the reaction of 2-amino-2-thiazoline and its analogs with carbethoxy isothiocyanate

Cited by 32 publications

References 12 publications

Lipid Membrane Adhesion and Fusion Driven by Designed, Minimally Multivalent Hydrogen-Bonding Lipids

Lipid Membrane Adhesion and Fusion Driven by Designed, Minimally Multivalent Hydrogen-Bonding Lipids

Hydrogen-Bonding Recognition-Induced Color Change of Gold Nanoparticles for Visual Detection of Melamine in Raw Milk and Infant Formula

Functionalized Au-Fe3O4 nanocomposites as a magnetic and colorimetric bimodal sensor for melamine

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