L Amino Acids and D-Glucose Bind Stereospecifically to a Colloidal Clay

Bondy, Stephen C.; Harrington, Marilyn E.

doi:10.1126/science.424749

Cited by 89 publications

(25 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Bonner & Flores (1973), Flores & Bonner (1974) and McCullough & Lemmon (1974) did not observe any selective adsorption (or polymerization) of amino acid enantiomers by kaolinite. Similar results seem to be obtained with bentonite (Bondy & Harrington, 1979).…”

Section: Discussionsupporting

confidence: 88%

“…Aspartic acid is adsorbed by kaolinite, but no selectivity for one or the other enantiomer was observed. More recently, Bondy & Harrington (1979) observed that L-leucine, L-aspartate and D-glucose bound to bentonite in a stereospecific manner to a much greater extent than did the homologous compounds that are rarely found in nature (D-leucine, D-aspartate and L-glucose). The difference in behaviour is explained by a difference in the properties when the molecules are covalently bound to, or complexed with, other molecules that are themselves chiral.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Stereoselectivity of montmorillonite in the adsorption and deamination of some amino acids

Siffert

Naidja

1992

Clay miner.

View full text Add to dashboard Cite

A B S T R A C T:Optical isomers deamination of L-and D-glutamic and aspartic amino acids and of their DL racemic mixtures has been achieved in the presence of Na-montmorillonite at pH = 6 and room temperature. The adsorption curves showed that the enantiomer adsorbed depends on the type of amino acid. Nevertheless, deamination reaction kinetics brought about a stereoselectivity of the clay mineral for the L-isomer and implicitly showed an unquestionable "structural chirality character" of the clay mineral.Since Bernal's hypothesis (1949) on the possible implication of clay minerals in the origin of life, several investigators (Paecht-Horowitz et al., 1970; Cairns-Smith, 1974, 1975 Lahav etal., 1978; Coyne etal., 1981; Coyne, 1985;Yamagishi, 1981 Yamagishi, , 1982Yamagishi, , 1983)have attempted to understand the action of clay minerals in the transformation and evolution of organic and bio-organic matter. Many investigators showed that the swelling clay minerals, especially montmorillonite, would be able to assume the role of a pseudo-enzyme (Mortland, 1984; Siffert & Naidja, 1987; Naidja & Siffert, 1989, 1990. The question which persists concerns the stereoselectivity of clay minerals in biochemical reactions, and in particular that raised by Degens et al. (1970) as to the cause of the L homochirality of amino acids in living organisms. It is necessary to note that organisms generally contain amino acids in their L-enantiomer form (Lavollay, 1980). Degens et al. (1970) reported a remarkable finding in connection with clay minerals, namely, that L,D-and D,L-aspartic acids in aqueous solution were polymerized at 90~ to differing extents by the catalytic action of kaolin. Thus the L-enantiomer was reported to polymerize to the extent of 25% and the D-isomer to the extent of only 3%. The authors concluded that an asymmetric synthesis of polypeptides had been accomplished on the clay surface and that polymers containing L-amino acids were formed preferentially to those containing D-enantiomers. A later report by Jackson (1971) purported to confirm these asymmetric polymerization findings, to show that the polymerization of aspartic acid failed to occur in the absence of kaolin as catalyst. Jackson also reported that L-phenylalanine was adsorbed by kaolinite to a higher extent than D-phenylalanine. In contrast to these observations, Bonner & Flores (1973) could find no evidence for the differential adsorption of D-versus L-phenylalanine by kaolin from either pH = 6 or pH = 2 solutions, using optical rotatory dispersion, gas chromatography and thin layer chromatography. However, optical rotatory dispersion measurements are unfortunately approximately within the experimental error of the observed rotations.9 1992 The Mineralogical Society

show abstract

Section: Discussionsupporting

confidence: 88%

mentioning

confidence: 99%

Stereoselectivity of montmorillonite in the adsorption and deamination of some amino acids

Siffert

Naidja

1992

Clay miner.

View full text Add to dashboard Cite

show abstract

“…Chiral discrimination of organic compounds by minerals has been a rich subject for speculation since the early suggestions by Goldschmidt 21 and Bernal 22 that quartz 23 or chiral clays, [24][25][26] respectively, may have been responsible for the origin of biomolecular homochirality. Scientists have subsequently worked out many mechanisms of chiral discrimination of molecules by crystal surfaces.…”

Section: Crystalsmentioning

confidence: 99%

Dendritic crystal growth, differential circular scattering, and the origin of biomolecular homochirality

Kahr¹,

Freudenthal²

2008

Chirality

View full text Add to dashboard Cite

Phthalic acid rapidly crystallizing in thin aqueous films is deposited radially and rhythmically as dendritic banded spherulites that have heterochiral meso-textures in hemi-circles. The chiral fields differentially scatter left and right circularly polarized light. A scenario for chiral amplification and the origin of biomolecular homochirality is thus proposed that combines the influences of crystals and light.

show abstract

“…The binding characteristics of l-amino acids and d-glucose stereo specific to the colloidal clay bentonite and the optical resolution of racemic metal chelae's have been studied by use of adsorption of a colloidal clay [8]. A wide variety of host molecules have been designed [9] to selectively entrap ions of different sizes or to provide pockets, which may capture neutral species, by intermolecular forces such as hydrogen-bonding functions, aromatic stacking interactions and dipole-dipole forces.…”

Section: Introductionmentioning

confidence: 99%

Resolution of d- and l-glucoses by chiral N-octyl-β-d-glycoside–Cu(II) complex adsorbed at the gas/liquid interface of small bubbles

Sakai

Miyazawa

Jitsumatsu

et al. 2010

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

L Amino Acids and D-Glucose Bind Stereospecifically to a Colloidal Clay

Cited by 89 publications

References 2 publications

Stereoselectivity of montmorillonite in the adsorption and deamination of some amino acids

Stereoselectivity of montmorillonite in the adsorption and deamination of some amino acids

Dendritic crystal growth, differential circular scattering, and the origin of biomolecular homochirality

Resolution of d- and l-glucoses by chiral N-octyl-β-d-glycoside–Cu(II) complex adsorbed at the gas/liquid interface of small bubbles

Contact Info

Product

Resources

About