Noncovalent Binding between Guanidinium and Anionic Groups:  Focus on Biological- and Synthetic-Based Arginine/Guanidinium Interactions with Phosph[on]ate and Sulf[on]ate Residues

Schug, Kevin A.; Lindner, Wolfgang

doi:10.1021/cr040603j

Cited by 534 publications

(280 citation statements)

References 254 publications

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“…The result is a moiety with six potential hydrogen bonding sites. The multiple hydrogen bonding abilities as well as its unique shape allow a guanidinium group to direct both electrostatic and hydrogen bonding with anionic and polar molecules [80]. When arginine interacts with phospholipids this takes the form of bi-or multi-dentate hydrogen bonding from simultaneous association with the phosphates of more than one lipid head group.…”

Section: The Arginines In the Tat Peptide Generate Negative Gaussian mentioning

confidence: 99%

Arginine‐rich cell‐penetrating peptides

et al. 2009

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a b s t r a c tArginine-rich cell-penetrating peptides are short cationic peptides capable of traversing the plasma membranes of eukaryotic cells. While successful intracellular delivery of many biologically active macromolecules has been accomplished using these peptides, their mechanisms of cell entry are still under investigation. Recent dialogue has centered on a debate over the roles that direct translocation and endocytotic pathways play in internalization of cell-penetrating peptides. In this paper, we review the evidence for the broad range of proposed mechanisms, and show that each distinct process requires negative Gaussian membrane curvature as a necessary condition. Generation of negative Gaussian curvature by cell-penetrating peptides is directly related to their arginine content. We illustrate these concepts using HIV TAT as an example.

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Section: The Arginines In the Tat Peptide Generate Negative Gaussian mentioning

confidence: 99%

Arginine‐rich cell‐penetrating peptides

et al. 2009

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“…Anion supramolecular chemistry involves the development and use of selective anion receptors. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] In fact, today a large number of coordination studies can be found in the literature describing a wide range of different ligands for anion coordination mainly involving hydrogen bonding, [15][16][17][18][19] electrostatic interactions [20][21][22][23][24][25][26][27] or coordination with suitable metal cations. [28][29][30][31][32][33] The nature of the binding sites and their specific spatial arrangement determine the binding constant with a certain anion and usually selective coordination can be found when a large host-guest complementarity is reached.…”

Section: -Introductionmentioning

confidence: 99%

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

2011

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“…11,12 As already noted, a detailed understanding of the noncovalent bonding pattern of these aggregates is of special interest since they reveal various contributions (salt bridge, hydrogen bridge, cooperative effects, etc), which are similar to those occurring in guanidinium-based carboxylate receptors (see review by Schug and Lindner). 13 Our previous calculations started from arginine monomer and dimer structures given in the literature, but to ensure that no minima are missed, extensive conformational searches were per-formed. These computations revealed a new global minimum, which possesses a completely different structural arrangement than the minimum given in the literature.…”

Section: Introductionmentioning

confidence: 99%

Conformational analysis of arginine in gas phase—A strategy for scanning the potential energy surface effectively

et al. 2007

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Abstract:The determination of all possible low-lying energy conformers of flexible molecules is of fundamental interest for various applications. It necessitates a reliable conformational search that is able to detect all important minimum structures and calculates the energies on an adequate level of theory. This work presents a strategy to identify low-energy conformers using arginine as an example by means of a force-field based conformational search in combination with high-level geometry optimizations (RI-MP2/TZVPP1). The methods used for various stages in the conformational search strategy are shown and various pitfalls are discussed. We can show that electronic energies calculated on a DFT level of theory with standard exchange-correlation functionals strongly underestimate the intramolecular stabilization resulting from stacked orientations of the guanidine and carbonyl moiety of arginine due to the deficiency of DFT to describe dispersion effects. In this case by usage of electron correlation methods, low energy conformers comprising stacked arrangements that are counterintuitive become favorable.

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Noncovalent Binding between Guanidinium and Anionic Groups: Focus on Biological- and Synthetic-Based Arginine/Guanidinium Interactions with Phosph[on]ate and Sulf[on]ate Residues

Cited by 534 publications

References 254 publications

Arginine‐rich cell‐penetrating peptides

Arginine‐rich cell‐penetrating peptides

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

Conformational analysis of arginine in gas phase—A strategy for scanning the potential energy surface effectively

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