The nature of chiral recognition: Is it a three-point interaction?

Davankov, V. A.

doi:10.1002/(sici)1520-636x(1997)9:2<99::aid-chir3>3.0.co;2-b

Cited by 228 publications

(179 citation statements)

References 14 publications

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“…on certain crystal faces were observed, then the problem of biological homochirality would be possible to comprehend.' ' Effective chiral selectivity by a crystal requires at least three noncolinear configuration-dependent points of interaction between the molecule and an acentric mineral surface (7). Most previous experimental studies of adsorption of organic molecules on mineral surfaces have focused on the symmetrybreaking effects of right-vs. left-handed quartz, which is the most common acentric mineral (8).…”

mentioning

confidence: 99%

Selective adsorption ofl- andd-amino acids on calcite: Implications for biochemical homochirality

Hazen

Filley

Goodfriend

2001

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

361

261

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The emergence of biochemical homochirality was a key step in the origin of life, yet prebiotic mechanisms for chiral separation are not well constrained. Here we demonstrate a geochemically plausible scenario for chiral separation of amino acids by adsorption on mineral surfaces. Crystals of the common rock-forming mineral calcite (CaCO3), when immersed in a racemic aspartic acid solution, display significant adsorption and chiral selectivity of D-and L-enantiomers on pairs of mirror-related crystal-growth surfaces. This selective adsorption is greater on crystals with terraced surface textures, which indicates that D-and L-aspartic acid concentrate along step-like linear growth features. Thus, selective adsorption of linear arrays of D-and L-amino acids on calcite, with subsequent condensation polymerization, represents a plausible geochemical mechanism for the production of homochiral polypeptides on the prebiotic Earth.

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mentioning

confidence: 99%

Selective adsorption ofl- andd-amino acids on calcite: Implications for biochemical homochirality

Hazen

Filley

Goodfriend

2001

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

361

261

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“…The IRMPD spectra of the ESI-formed proton-bound complexes of the R,R,R,R-and S,S,S,S-enantiomers of a bisA C H T U N G T R E N N U N G (diamido)-bridged basket resorcin [4]arene (R and S) with cytosine (1), cytidine (2), and cytarabine (3) were measured in the region 2800-3600 cm À1 . Comparison of the IRMPD spectra with the corresponding ONIOM (B3LYP/6-31(d):UFF)-calculated absorption frequencies allowed the assessment of the vibrational modes that are responsible for the observed spectroscopic features.…”

Section: Introductionmentioning

confidence: 99%

“…Structures of the flattened-cone bisA C H T U N G T R E N N U N G (diamido)-bridged basket resorcin [4]arenes R and S and of cytosine (1), cytidine (2), and cytarabine (3). Inset: structure of the R enantiomer in its most-stable "openwinged" conformation.…”

Section: Introductionmentioning

confidence: 99%

“…[39] spectively) in the flattened cone conformation. Cytidine (2) and its epimer cytarabine (3) were used as chiral guests because of their ability to establish stable proton bonds with the amidocarbonyl groups on the basket resorcin [4]arene. [39][40][41] For comparison, the study was also extended to cytosine (1), which was used as a simplified achiral model of compounds 2 and 3.…”

Section: Introductionmentioning

confidence: 99%

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Chirality Effects on the IRMPD Spectra of Basket Resorcinarene/Nucleoside Complexes

Filippi

Fraschetti

Piccirillo

et al. 2012

Chemistry A European J

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The IRMPD spectra of the ESI‐formed proton‐bound complexes of the R,R,R,R‐ and S,S,S,S‐enantiomers of a bis(diamido)‐bridged basket resorcin[4]arene (R and S) with cytosine (1), cytidine (2), and cytarabine (3) were measured in the region 2800–3600 cm−1. Comparison of the IRMPD spectra with the corresponding ONIOM (B3LYP/6‐31(d):UFF)‐calculated absorption frequencies allowed the assessment of the vibrational modes that are responsible for the observed spectroscopic features. All of the complexes investigated, apart from [R⋅H⋅3]+, showed similar IRMPD spectra, which points to similar structural and conformational landscapes. Their IRMPD spectra agree with the formation of several isomeric structures in the ESI source, wherein the N(3)‐protonated guest establishes noncovalent interactions with the host amidocarbonyl groups that are either oriented inside the host cavity or outside it between one of the bridged side‐chains and the upper aromatic nucleus. The IRMPD spectrum of the [R⋅H⋅3]+ complex was clearly different from the others. This difference is attributed to the effect of intramolecular hydrogen‐bonding interactions between the C(2′)OH group and the aglycone oxygen atom of the nucleosidic guest upon repulsive interactions between the same oxygen atom and the aromatic rings of the host.

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“…Many authors, such as Ogston, 1 Cramer, 2 and more recently Davankov, 3 have tried to understand the nature of interactions that are needed for a chiral selector to recognize enantiomers. The importance of this topic is also due to the fact that the activity of most biological molecules, indeed in protein recognition phenomena, seems to be due to ability of receptors to interact with amino acid residues in order to give inclusion complexes or supramolecular species.…”

Section: Introductionmentioning

confidence: 99%

A spectrofluorimetric study of binary fluorophore–cyclodextrin complexes used as chiral selectors

et al. 2005

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Abstract-Six binary complexes between three fluorophores (pyrene, xanthone and anthraquinone) and b-cyclodextrin (b-CD) or heptakis-(6-amino)-(6-deoxy)-b-cyclodextrin (am-b-CD) were tested at two pH values (8.0 and 9.0) as chiral selectors for three a-amino acids chosen as model. The conditional constant (b 2T ) values for ternary complexes (fluorophore-CD-amino acid), determined by means of fluorescence spectroscopy, showed that the binary complexes are suitable receptors for chiral recognition. The effect of a-amino acids on stability and stoichiometric ratio of the binary complexes has also been studied. The binary complexes were in most cases stabilized by adding the ternary agent. The trend of stoichiometric ratios found is supported by variations in fluorescence spectra. Those relative to pyrene (Py) show little changes going from binary to ternary complexes, while those recorded in the presence of xanthone (Xan) give the most significant variations underlining a deep reorganization of guest. Anthraquinone (Aq) shows an intermediate behavior.

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The nature of chiral recognition: Is it a three-point interaction?

Cited by 228 publications

References 14 publications

Selective adsorption ofl- andd-amino acids on calcite: Implications for biochemical homochirality

Selective adsorption ofl- andd-amino acids on calcite: Implications for biochemical homochirality

Chirality Effects on the IRMPD Spectra of Basket Resorcinarene/Nucleoside Complexes

A spectrofluorimetric study of binary fluorophore–cyclodextrin complexes used as chiral selectors

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