Hydrogen bonding between nucleic acid bases and carboxylic acids

Lancelot, G.

doi:10.1021/ja00463a044

Cited by 90 publications

(57 citation statements)

References 3 publications

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“…Gratifyingly, in keeping with our assumptions in the design of the monomers, (4) exhibited a much higher association constant with (1) and (2) than did (3), thus demonstrating the effect of the "extra" hydrogen-bonding interaction. While there is also the possibility that (3) might self-associate, which would also reduce its effectiveness in forming a complex with (1) or (2), previous studies have shown that in CDCI 3 such self-association may be considered negligible [10]. The use of monomer (5) illustrates the increase in association constant obtained when switching from amino-to amido-functionalities; the association constants obtained here are also consistent with previous studies [11].…”

Section: Methodssupporting

confidence: 90%

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

et al. 2002

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The interaction of N1-substituted uracils (cyclohexyl (1) and benzyl (2)) with three polymerisable recognition elements, the novel monomers 9-(3/4-vinylbenzyl)adenine (3) and 2,6-diamino-9-(3/4-vinylbenzyl)purine (4) and the previously synthesised monomer 2,6-bis(acrylamido)pyridine (5), has been studied via1H NMR in deuterio-chloroform solution. MIPs against (2) have been prepared using each of the monomers and tested in the chromatographic mode. The effect of the number and type of hydrogen bonds formed between the templates and the functional monomers is reflected in the values of the apparent association constants obtained from the solution study and by the performance of the subsequently prepared MIPs in the chromatographic mode.

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Section: Methodssupporting

confidence: 90%

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

et al. 2002

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“…This template is known to interact strongly with carboxylic acids in aprotic solvents [20] and a significant part should exist in the complexed form prior to polymerisation, as indicated in Figure 1. Complexation was supported by pronounced shifts observed for the exocyclic amine and aromatic 1 H-NMR signals of the template upon addition of MAA (NH 2 : -2,4 ppm; H 2 : +0,1 ppm; H 8 : -0,1 ppm).…”

Section: Discussionmentioning

confidence: 99%

Studies on the Process of Formation, Nature and Stability of Binding Sites in Molecularly Imprinted Polymers

et al. 2002

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In Molecular Imprinting the nature of the templated binding sites and the mechanism of their formation are still poorly understood. For this reason our groups are carrying out fundamental studies concerning known imprinting protocols, with the primary aim of shedding light on the role of the template in the different steps of the polymerisation, from the formation of primary chains to the build-up of the porous structure. In this paper we report our initial results concerning copolymers of methacrylic acid (MAA) and ethyleneglycol dimethacrylate (EDMA) and their formation in presence or absence of the templates 9-ethyladenine, ametryn or terbutylazine. Monitoring the monomer disappearance by 1H-NMR showed that the presence of templates such as 9-ethyladenine significantly retarded the polymerisation but otherwise had minor influence on the relative reactivity of the monomers. The latter appeared in most cases to be stoichiometrically incorporated into the polymer. The signals arising from the template experienced little or no shift in the early stage of the polymerisation, although pronounced broadening was observed. By delaying the addition of the template, it was observed that binding sites with high selectivity could be induced more than one hour after the gel point of the system had been passed. Finally, the results of post-polymerisation curing on the dry and swollen state porosities and the recognition properties of terbutylazine imprinted polymers are reported. This treatment when performed at temperatures between 100-120°C, slightly enhanced the selectivity of the polymers, whereas at higher temperatures the polymers lost their molecular recognition properties. Swollen state porosity derived from inverse size exclusion chromatography (ISEC) revealed an interesting sharpening of the pore size distribution for the imprinted compared to the non-imprinted polymers.

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“…The interaction of positive charges of Na ϩ or Ca 2ϩ cations would displace ACh in a manner similar to that described in histamine release from mast cell granules (7,8). ATP can interact through the nitrogen atoms of the purine ring or the phosphate residues, as nitrogen atoms can establish hydrogen bonds with carboxylic radicals (37)(38)(39). A second possibility of interaction of ATP is based on the fact that ATP easily complexes with divalent cations (40)(41)(42).…”

Section: (F and H) Western Blot Detection Of Sv2 Content In Immunoprementioning

confidence: 96%

Control of neurotransmitter release by an internal gel matrix in synaptic vesicles

Reigada

Díez‐Pérez

Gorostiza

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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Neurotransmitters are stored in synaptic vesicles, where they have been assumed to be in free solution. Here we report that in Torpedo synaptic vesicles, only 5% of the total acetylcholine (ACh) or ATP content is free, and that the rest is adsorbed to an intravesicular proteoglycan matrix. This matrix, which controls ACh and ATP release by an ion-exchange mechanism, behaves like a smart gel. That is, it releases neurotransmitter and changes its volume when challenged with small ionic concentration change. Immunodetection analysis revealed that the synaptic vesicle proteoglycan SV2 is the core of the intravesicular matrix and is responsible for immobilization and release of ACh and ATP. We suggest that in the early steps of vesicle fusion, this internal matrix regulates the availability of free diffusible ACh and ATP, and thus serves to modulate the quantity of transmitter released.

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Hydrogen bonding between nucleic acid bases and carboxylic acids

Cited by 90 publications

References 3 publications

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

Studies on the Process of Formation, Nature and Stability of Binding Sites in Molecularly Imprinted Polymers

Control of neurotransmitter release by an internal gel matrix in synaptic vesicles

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