Abstract
Chapter 1 considers the possible relationships of earthly clays and other minerals to the origin of chirality in organic molecules. Attempts to establish experimental evidence of asymmetric adsorption on clays were unsuccessful, but the search for chirality did find naturally occurring enantiomorphic crystals like quartz. Asymmetric adsorption of organic molecules on quartz crystals such as separation of racemic mixtures, like Co or Cr complexes, alcohols and other compounds, allowed for the conclusion that quartz crystals can serve as possible sources of chirality but not of homochirality. This latter conclusion results from the finding that all studied locations of quartz crystals contain equal amounts of d- and l-forms. The preparations of synthetic adsorbents such as imprinting silica gels are also considered. More than 130 references are analyzed.
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References
Bernal J.D. (1951) The Physical Bases of Life, Routlege & Regan Paul, London, p. 34.
Cairns-Smith G. (1982) Genetic takeover and the mineral origin of life, Cambridge, NY.
Grim R.E. (1968) Clay Mineralogy, McGraw Hill, NY. pp. 57–69.
Wellner D. (1979) (Comments) Sci., 206, 484.
Kahlen W., Wagner H.H. and Holderich W.F. (1998) Zeolite effect in the enantioselective trans-hydrogenation over a Co-Salen “Ship-in-the-botttle” complex, Catal. Lett., 54, 85–89.
Degens E.T., Matheja J. and Jackson T.A. (1970) Template catalysis: asymmetric polymerization of amino acids on clay minerals, Nat. 227, 492–493.
Bondy S.C. and Harrington M.E. (1979) L-Amino acids and D-glucose bind stereospecifically to a colloidal clay, Science, 203, 1243–1244.
Julg A. (1986) Adsorption sur la kaolinite et homochiralite L des acides amines des proteines, Compt. rend., Ser.2, 303, 1773–1776.
Julg A. (1987) Synthese asymmetrique sur la kaolinite de l'aminopropionitrile, precurseur de l'alanine et homochiralite des acides amines des proteines, Compt. rend., Ser.2, 305, 563–565.
Julg A. (1988) Stabilite relative des deux formes inverses optiques de la kaolinite. Application a l'homochiralite L des acides amines des proteines, Compt. rend. Ser.2, 306, 1153–1156.
Field B.O. and Spencer J.E.D. (1990) The synthesis of amino acids and sugars on an inorganic template from constituents of the prebiotic atmosphere, Origin of Life and Evolution of Biosphere, 20, 233–248.
Gabel N.W. and Ponnamperuma C. (1967) Model for origin of monosaccharides, Nat. 216, 453–455.
Goldanskii V.I. (1996) Formaldehyde as hypothetical primer of biohomochirality, in Physical Origin of Homochirality in Life, Amer. Inst. Phys. Conferences, Santa Monica CA, Proceedings 379, 1995 (Cline D.B. (ed.), AIP Press, Woodbury, N.Y. pp. 50–54.
Osinovskii A.G. and Erofeev B.V. (1982) On opportunity of asymmetric condensation of formaldehyde into sacharides, in “Coordinating Meeting on asymmetric catalysis”, 1982, Sci. Council Acad. Sci. on Catal. Inst. Org. Chem. Acad. Sci. USSR and Dept Chem. & Chem. Technol. Acad. Sci. Georgian SSR, Tbilisi State Univ., Abstracts, Borjomi.Georgia, p. 43–44.
Osinovskii A.G. and Erofeev B.V. (1986) Asymmetric synthesis of carbohydrates based on formaldehyde on catalysts modified with L-amino acid esters in “ First Republic Meeting on Asymmetric Reactions”, Batumi, Gruz. SSR (Georgia), Abstracts, p.41.
Jackson T.A. (1971) Evidence of selective adsorption and polymerization of the L-optical isomers of amino acids relative to the D-optical isomers on the edge of facets of kaolinite, Experientia, 27, 242–243.
Kavasmaneck P.R. (1978) Asymmetric adsorption by quartz: a model for the origin of optical activity, Diss.Thesis, Stanford Univ., 246 pp., Diss. Abstr. Int. B. 36 (9) 4508–4509; Chem. Abstr. 1976, 84, 146534.
Bonner W.A. (1979) Experiments on the abiotic origin and amplification of optical activity, Stud.Phys.Theor.Chem. (Origin Opt. Act.) Nature 7, 5–20.
Flores J.J. and Bonner W.A. (1974) Asymmetric polymerization of aspartic acid enantiomers by kaolin, J. Mol. Evol., 3, 49–56.
McCullough J.J. and Lemmon R.M. (1974) Question of the possible asymmetric polymerization of aspartic acid on kaolinite, J. Mol. Evol. 3, 57–67.
Jackson T.A. (1979) Stereospecific sorption of L - amino acids by colloidal clay, Sci., 296, 483–484.
Thomson T.D (1979) Clays, Clay Minerals, 21, 242.
Bondy S.C. and Harrington M.E. (1979) The preparation high-affinity binding of the biological forms of amino acids and hexose stereoisomers to bentonite, Stud. Phys. Theor. Chem. 7, (Origin of Optical Activity in Nature), p.141–149.
a) Friebele E., Shimoyama A., Hare P.E. and Ponnamperuma C. (1981) Adsorption of amino acid enantiomers by Sodium montmorillonite, Origin Life, 11, 173–184.
b) Friebele E., Shimoyama A., Hare P.E. and Ponnamperuma C (1980) Adsorption of protein and nonprotein amino acids on a clay minerals; a possible role of selection on chemical evolution, J. Mol. Evol. 16, 269–278.
Bonner W.A., Van Dort M.A. and Flores J.J. (1974) Quantitative gas chromatographic analysis of leucine enantiomers. A comparative study, Anal. Chem. 46, 2104–2106.
Navarro-Gonzalez B., Khanna P.K. and Ponnamperuma C. (1993) in Ponnamperuma C. and Cella-Flores J. (Eds.) Chemical Evololution: Origin of Life Proc. Trieste Conf. Chem. Evolution and Origin of Life, 1992, A Deepak Publ., Hampton, VA.
Youatt J.B. and Brown R.D. (1981) Origin of chirality in Nature. A reassessment of the postilated role of bentonite, Sci., 212, 1145–1146.
Bonner W.A. (1991) The origin and amplification of biomolecular chirality, Origin Life, Evol. Biosphere, 21, 59–111.
Bonner W.A. (1996) The Quest for Chirality, Physical Origin of Homochirality in Life, Amer. Inst. Phys. Conferences, Santa Monica CA, 1995, Proceedings 379, Cline D.B. (ed.) AIP Press, Woodbury, N.Y. pp.17–49.
Lemmlein G.G. (1944) The relative number of left-and right-handed quartz crystals, Coll. Mineralog. Soc. (russ.) 73, N 2–3, 94–100.
Lemmlein G.G. (1936) On twisted quartz, Dokl. Acad. Nauk SSSR 4, 279–282.
Hylleraas E. (1927) Equilibrium position of the atom, double refraction and optical rotation power of beta-quartz, Z. Phys., 44, 871.
Cedy W. (1946) Piezoelectricity. An Introduction to the Theory and Application of Electromechanical Phenomena in Crystals, 1st Ed. N.Y., London.
Mason S.F. (1984) Origin of biomolecular handedness, Nat., 311, 19–23.
Tranter G.E. (1985) Parity-violation energy differences of chiral minerals and the origin of biomolecular homochirality, Nat., 318, 172–173.
MacDermott A.J. (1993) The weak force and the origin of life, in Chemical evolution. Origin of life, (Ponnamperuma C. and Chela-Flores J. (eds.), Deepak Hampton, pp. 85–99.
MacDermott A.J. (1996) The weak force and SETH: The Search for Extra-Terrestrial Homochirality, in Physical Origin of Homochirality in Life, Amer. Inst. Phys. Conf., Santa Monica CA, Proceedings 379, 1995, Cline D.B. (ed.), AIP Press. Woodbury, N.Y. pp. 241–254.
Vistelius A.B. (1950), The frequency of enantiomorphic quartz types, Zapiski Vsesoyusnogo Mineralog. Obshch. (Collections of All-Union Mineralogical Soc. USSR, russ.), V.79, p. 191–195.
Frondel C. (1978) Characters of quartz fibers, Amer. Mineralogist (J. Mineral. Soc. Amer.) 63, N 1–2,17–27.
Frondel C. (1962) Silica minerals, in Dana's System of Mineralogy. Silica minerals, Wiley & Sons, NY. VII Auflage. Bd. 3. S.16.
Heritsch H. (1952) Die Verteilung von Rechts-und Links Quarzen in Schriftgranaten, Tschermaks Mineral, Petrogr. Mitt. 3, 115–125.
Kozlovski M.I. (1962) Spiral growth and dissolution of crystals, in Growth of Crystals, Shubnikov A.V. and Sheftel N.N. (eds.).V.3, Consultants Bureau, N.Y. p.101–106.
a) Klabunovskii E.I. and Thiemann W.(2000) The role of quartz in the origin of optical activity on Earth, Origins Life Evol. Biospher 30, 431–434.
b) Klabunovskii E.I.(2001) Can enantiomorphic crystals like quartz play role in the origin of homochirality on Earth, Astrobiology 1, 127–131.
c) Klabunovskii E.I. (2002) The role of enantiomorphic in the origin of chirality on Earth and other planets, In Second European Workshop on Exo+Astrobiology, Graz, Austria, Abstr., p. 9.
Gross G. (1972) Zerstoerungsfreie Statisch-morphologische Untersuchung eines Quartzfundes, Schweiz. Mineral. Petrogr. Mitt. 52, 523–535.
Rein D. (1992) Die wunderbare Haendigkeit der Molekuele vom Ursprung der Leben aus der Asymmetrie der Natur, Birkhuser Verlag, Basel, Boston, Berlin.
Thompson M.R. (1937) How to tell right-handed and left-handed quartz crystals, Rocks and Minerals N 12.
Holzapfel L. (1951) Silizium Verbindungen in biologischen Systemen. Organische Kieselsaeure - Verbindungen. XX Mitt., Z. Electrochem. 55, 577.
Seifert H. (1955) Ueber orientierende Abscheidungen von Aminosaeure auf Quarz, Naturwiss. 42, 13.
Kleber W. and Meyer K (1957) Asymmetrische effecte bei der Epitaxie von d-Campher auf Biotit und Calcit, Naturwiss. 44, 373–374.
Henderson G.M. and Rule H.G. (1939) A new method of resolving a racemic compounds. J. Chem. Soc., 1568–1573.
a) Klabunovskii E.I. and Patrikeev V.V. (1951) On mechanism of asymmetrizing action of metal catalysts deposited on right and left quartz, Dokl. Acad. Sci. USSR. 78, N3, 485–487, Chem. Abstr. 1951, 45, 7860a.
b) Harada K. (1977) The recent studies on the origin of optical activity. Kagaku no Ryoki, 31, 1–11.
Ohara M., Fujita I. and Kwan T. (1962) The selective adsorption of optical antipodes as revealed by the chromatographic technics, Bull. Chem. Soc. Jpn, 35, 2049–2051.
Tsuchida R., Kobayashi M. and Nakamura A. (1935) The configuration of chlorobisdi-methylglyoximoammine-Cobalt, Bull. Chem. Soc. Jpn. 11, 38–40.
Nakamura A. and Tsuchida R. (1954) Synthesis of the tris-(dimethylglyoximo)-cobaltate (III). J. Amer. Chem. Soc. 76, 3103.
Karagunis G. and Coumoulos G. (1938) A new method of resolving a racemic compounds, Nat. 142,162–163.
Ikeda Y. (1954) Partial resolution of racemic hydroperoxydes by asymmetric adsorption on rock quartz, Bull. Liberal Arts, Coll. Wakayama Univ. (Nat. Sci.) 4, 27–28; Chem. Abstr. 49, 9583 (1955).
Kuebler J.R. and Bailar J.C. (1952) The stereoisomerism of complex inorganic compounds. XIV. Studies upon the stereochemistry of saturated tervalent nitrogen compounds, J. Amer. Chem. Soc., 74, 3535–3538.
Bush D.M. and Bailar J.C. (1953) Stereochemistry of complex inorganic compounds. XVII. The stereochemistry of hexadentate ethylenediaminetetraacetic acid complexes, J. Amer. Chem. Soc. 76, 4574–4575.
Das Sarma B. and Bailar J.C. (1955) The stereochemistry of metal chelates with polydentate ligands P.1, J. Amer. Chem. Soc. 77, 5476–5480.
Schweizer G.K. and Talbott C.K (1950) Resolution of optically active inorganic stereoisomers by adsorption on quartz, J. Tennessi Acad. Sci. 25, 143–147 (1950); Chem. Abstr. 46, 11004.
Kamai G.Kh., Klabunovskii E.I., Gatilov Yu.F. and Khodakov G.S. (1961) Resolution of tertiary arsenic compounds into optical isomers using asymmetric adsorption on natural dissymmetric adsorbents, Dokl. Acad. Sci. USSR, 139, 1112–1113, Chem. Abstr. 1962, 56, 41f.
Chernyaev I.I., Korablina L.S. and Muraveiskaya G.S. (1965) On optical resolution and photochemical isomerization of asymmetric cis-diammines, Zh. neorg. khim. (J. Inorg. Chem. (russ.), 10, 1045–1052.
Moeller T. and Gulyas E. (1958), The partial resolution of certain inner complexes by means of a chromatographic technique, J. Inorg. Nucl. Chem., 5, 245–248.
Sievers R.E., Moshier R.W. and Morris M.L. (1962) Resolution of Chromium (III)-hexafluoroacetylacetonate by gas chromatography, Inorg. Chem. 1, 960–967.
Bush D.H. and Bailar J.C. (1954) The optical stability of Berillium complexes, J. Amer. Chem. Soc. 76, 5352–5353.
McLaren A.D. and Estermann E.F. (1954) The adsorption and reactions of enzymes and proteins on kaolinite, Acta Biochem. Biophys. 61, 158–173.
Schwab G.M. and Wahl B. (1956) Beitraege zur Struktur der organischen Kieselsaeure, Naturwiss. 43, 513–514.
Amariglio-Simon A. (1967) Theses, Etude critique des reactions asymetriques sur quartz et des conditions de stereospecificite dans les interactions moleculaires, Univ. Nancy.
Amariglio A., Amariglio H., and Duval X. (1968) La synthese asymetrique, Ann. chim. 3, 5–25.
Amariglio A., Amariglio H. and Duval X. (1968) Essais de reactions dissymetrique sur quartz optiquement actif, Helv. Chim. Acta. 51, 2110–2132.
Amariglio A. and Amariglio H. (1971) in Chemical Evolution and Origin of Life, Buvet E.R. and Ponnamperuma C. (eds.), North-Holland Publ. Amsterdam, p. 63.
Bonner W.A., Kavasmaneck P.R. and Martin F.S. (1974) Asymmetric adsorption of alanine by quartz, Sci. 186, 143–144.
Bonner W.A., Kavasmaneck P.R., Martin F.S. and Flores J. (1975) Origin Life, 6, 367.
Bonner W.A. and Kavasmaneck P.R. (1976), Asymmetric adsorption of DL-alanine hydrochloride by quartz., J. Org. Chem., 41, 2225–2226.
Kavasmaneck P.R. and Bonner W.A. (1977) Adsorption of amino acid derivatives by d-and l-quartz, J. Amer. Chem. Soc., 99, 44–50.
Furoyama S., Sawada M., Hashiya K. and Morimoto T. (1982) Asymmetric adsorption of alanine by quartz powder from ethanol solution, Bull. Chem. Soc. Jpn. 55, 3394–3397.
Kawashiro K., Morimoto S., Yoshida H. and Sugiura K. (1977) The synthesis and chromatography of peptide nitriles, Origin Life, 8, 347–353.
Gillard R.D. and da Luz de Jesus J.D.P. (1979) Studies on the origin of asymmetry. Part I. Optically active crystals as selective adsorbents, J. Chem. Soc., Dalton Trans. 1779–1782.
Chandrasekhar S. (1953) The optical rotatory dispersion of cinnabar, Proc. Indian Acad. Sci., 37A, 697–703.
Chandrasekhar S. (1954) The rotatory dispersion of benzil, Proc. Indian Acad. Sci., 39A, 243–253.
Chandrasekhar S. (1953) A redetermination of the rotatory dispersion of Sodium chlorate, Proc. Indian Acad. Sci., 37A, 458–67.
Ferroni E. and Cini R. (1960) The resolution of complex antipodes by optically active solids, J. Amer. Chem. Soc., 82, 2427–2428.
Kondepudi D.K., Kaufman R.J. and Singh N. (1990) Chiral symmetry breaking in sodium chlorate crystallization, Sci. 250, 975–976.
Bonner W.A., Blaire N.E. and Dirbas F.M. (1981) Experiments on the abiotic amplification of optical activity, Origin Life, 11, 119–134; 1975, 6, 187–194.
a) see also “Generation and Amplification of Chirality in Chemical Systems, Thiemann W. (ed.). Proc. Second International Symposium, Univ. Bremen, July 16, 1980, Origin of Life, 1981, V.11, 194 pp., D.Reidel Publ.Co., Dordrecht.
b) Bonner W.A (1979) in Origin of Optical Activity in Nature, Stud. Phys. & Theoret. Chem., N 7, Walker D.C. (ed.), Chem. Dept. Univ. British Columbia, Canada, Elsevier Sci. Publ. Co., Amsterdam, Oxford, NY, pp. 5-20
Polyakov M.V. (1931) Adsorption properties and structure of silica gel, Zh. Fiz. Khim. (J. Phys. Chem., russ.) 2, 799–805.
Vysotskii Z.Z. and Polyakov M.V. (1956) The preparation of specific adsorbents, Zhurn. Fiz. Khim. (J. Phys. Chem., russ.) 30, 1901–1902.
Dickey F.H. (1949) The preparation of specific adsorbents, Proc. Natl. Acad. Sci. USA, 35, 227–229.
Dickey F.H. (1955) Specific adsorption, J. Phys. Chem. 59, 695–707.
Pauling L. and Campbell D.H. (1942) The production of antibodies in vitro, Science, 95, N 2469, 440–441.
Pauling L. (1940) A theory of the structure and process of formation of antibodies, J. Amer. Chem. Soc., 62, 2643–2657.
Morrison J.L., Worsley M., Shaw D.R. and Hodgson G.W. (1959) The nature of the specificity of adsorption of alkyl orange dyes on silica gels, Can. J. Chem. 37, 1986–1995.
Kempe M., Fischer L. and Mosbach K. (1993) Chiral separation using molecularly imprinted heteroaromatic polymers, J. Mol. Recogn. 6, 25–29.
Kempe M. and Mosbach K. (1994) Chiral recognition of N-alpha-protected amino acids and derivatives in non-covalently imprinted polymers, Int. J. Peptide Protein Research, 44, 603–606.
Kempe M. and Mosbach K. (1994) Direct resolution of naproxen on a noncovalently molecularly imprinted chiral stationary phase, J. Chromatogr. 664, 276–279.
Ramstrom O., Yu C. and Mosbach K. (1996) Chiral recognition in adrenergic receptor binding mimics prepared by molecularly imprinting polymers, J. Mol. Recogn. 9, 691–696.
Bartels H., Prijs B. and Erlenmeyer H. (1966) Ueber spezifisch adsorbierende Silicagele, Helv. Chim. Acta 49, 1621–1625.
Erlenmeyer H. and Bartels H. (1964) Ueber das Problem der Aehnlichkeit in der Chemie. Ueber spezifisch adsorbierende Silicagele. II., Helv. Chim. Acta, 47, 1285–1288.
Erlenmeyer H. and Bartels H. (1965) Ueber spezifisch adsorbierende Silicagele. IV., Helv. Chim. Acta 48, 301–303.
Haldeman R.G. and Emmett P.H. (1955) Specific adsorption of alkyl orange dyes on silica gel, J. Phys. Chem., 59, 1039–1043.
Waksmundzki A.J., Oscik J., Rozylo J. and Matusewicz J. (1962) Structure and adsorption properties of specific adsorbents, Folia Soc. Sci. Lublin 2, 149–154.
Waksmundzki A., Wawrzynowicz T. and Wolski T. (1962) Adsorption properties of silica gels precipiated in the presence of some alkaloids, Ann. Univ. Mariae Curie-Sklodowska, Liblin-Polonia. Sect. AA, 17, 27–38.
Bernhard S.A. (1952) The preparation of specific adsorbents, J. Amer. Chem. Soc., 74, 4946–4947.
Patrikeev V.V., Kozarenko T.D. and Balandin A.A. (1962) On specific polycondensation of amino acid esters, Izv. AN SSSR. Otdel. Khim. Nauk. pp. 170–171.
Patrikeev V.V., Smirnova Z.S. and Maksimova G.I. (1962) Some biological properties of specifically formed silica, Dokl. Acad. Nauk SSSR 146, 707–709.
Balandin A.A., Patrikeev V.V., Sholin A.F., Bychenkova L.Ya. and Taber A.M. (1966) The giving of stereospecificity to hydrogenation catalysts by using specific formed carrier-silica gel, Dokl. Acad. Sci. USSR., 169, 1362–1365.
Sholin A.F., Patrikeev V.V. and Balandin A.A. (1967) Selective adsorbing silica gels, the possibility of their applications in the catalysis. Nature of their specificity, Proc. Int. Symp. on Mechanism of Heterogeneous Catalysts and Properties of Catalysts, Sofia, Abstracts, Publ. Bulgar Acad. Sci., 1967, p. 72.
Jencks W.P., Catalysis in Chemistry and Enzymology, McGraw Hill, N.Y., 1969.
Tramontano A., Janda K.O. and Lerner R.A. (1986) Catalytic antibodies, Science, 234, 1566–1570.
Ekberg B. and Mosbach K. (1989) Molecular imprinting: a technique for producing specific separation materials, Trends Biotechnol. 7, 92–96.
Wulff G. (1988) Selective binding to polymers via covalent bonds, The construction of chiral cavities as specific receptor sites, Pure Appl. Chem., 54, 2093–2102.
Matsuishi T., Shimada T. and Morihara K. (1992) Definite evidence for enantioselective catalysis over “Molecular Footprint” catalytic cavities chirally imprinted on a Silica (alumina), Chem. Lett., 1921–1924.
a) Morihara K., Kurihara S. and Suzuki J. (1988) Footprint Catalysis. I. A new method for designing “Taylor-Made” catalysts with substratespecificity: silica (alumina) catalysts for butanolysis of benzoic anhydride, Bull. Chem. Soc. Jpn. 61, 3991–3998.
b) Morihara K., Nishihata E., Kojima M. and Miyake S. (1988) Footprint Catalysis. II., Molecular recognition of footprint catalytic sites, Bull. Chem. Soc. Jpn. 61, 3999–4003.
Morihara K., Takiguchi M. and Shimada T. (1994) Footprint catalysis. XI., Molecular footprint cavities with chiral amines and their chiral molecular recognition, Bull. Chem. Soc. Jpn. 67, 1078–1084.
Morihara K., Kurokawa M., Kamata Y. and Shimada T. (1992) Enzymelike enantioselective catalysis over chiral ‘Molecular Footprint’ cavities on a silica (alumina) gel surface, J. Chem. Soc., Chem. Comm., 358–360.
Davis M.E., Katz A. and Ahmad W.R. (1996) Rational catalysts design via imprinted nanostructured materials, Chem. Mater., 8, 1820–1839.
Kaiser G.G. and Anderson J.T. (1992) Sorbents for liquid chromatography based on the footprint principle, Fresenius J. Analyt. Chem., 342, 834–838.
Heilman J. and Maier W.F. (1994) Selective catalysis on silicon dioxide with substarte-specific cavities, Angew. Chem., Int. Ed. Engl., 33, 471–473.
Curti R. and Colombo U. (1951) Separatione degli antipodi ottici dell'acido camfosolfonico mediante cromatografia su assorbenti specifici, Chim. Ind. 23, 103.
Curti R., Colombo U. and Clerici F (1952) Cromatografia con adsorbenti specifici, Gazz. Chim. Ital. 82, 491–502.
Beckett A.H. and Anderson P. (1959) “Footprints” in adsorbents, J. Pharm. Pharmacol. Suppl. 11, 258 T-260 T.
Beckett A.H. and Youssef H.Z. (1963) Active sites in stereoselective adsorbents as models of drug receptors and enzyme active sites, J. Pharm. Pharmacol. Suppl. 15, 253 T-266 T.
a) Hunnis, M., Rufinska A. and Maier W. F. (1999) Selective surface adsorption versus imprinting in amorphous silicas, Micropor. Mesopor. Mater. 29. 389–403.
b) Maier W.F. (1998) Amorphous microporous mixed oxides, new selective catalysts with chemo-and shape-selective properties, Prep. Symp. Amer. Chem. Soc., Div. Fuel Chem. 43, 534–537.
Klabunovskii E.I., Volkova L.M. and Agronomov A.E. (1961) On new method of preparation of stereospecific silicas, Izv. Akad. Nauk. SSSR. Otdel. Khim. Nauk, p. 2101, Chem. Abstr. 1968, 56, 9928a.
Klabunovskii E.I. and Volkova L.M. (1967) On optically active alkyloxyand alkylchloro-silanes as precursors for preparation of stereospecific silicas and organosilicium polymers, Izv. Akad. Nauk. SSSR. Ser. Khim. pp. 863–865, Chem. Abstr.1967, 67, 43354u.
Andrianov K.A., Mamedov A.A., Volkova L.M. and Klabunovskii E.I. 1969) Optically active menthoxy-, menthoxymethylethoxy(menthoxy)–silane, Izv. Akad. Nauk. Ser. Khim. pp 2305–2307, Chem. Abstr. 1970, 72, 43888z.
Klabunovskii E.I., Agronomov A.E., Volkova L.M. and Balandin A.A. (1963) On adsorption of racemic and (+)-isomer of sec-butanol on specific silicas, Izv. Akad. nauk. SSSR. Otdel. Khim. Nauk, pp. 228–234, Chem. Abstr. 1963, 58, 13170h.
Klabunovskii E.I., Godunova L.F. and Balandin A.A. (1966) On optically active organosilicium polymers, Vysokomol. soed. (russ.) 8, 441–443, Chem. Abstr. 1966, 64, 19815f.
Sholin A.F., Patrikeev V.V., Agronomov A.E. and A.A. Balandin (1968) Adsorption of d–and dl-sec-butylamine and benzene on titanogels, Kolloid. Zh. (Colloid J., russ.) 30, 450–454.
Patrikeev V.V., Balandin A.A., Klabunovskii E.I., Mardashev Yu.S. and Maksimova G.I. (1960) Selectivity of action in relation of optical isomers of adsorbents formed in the presence of bacteria, Dokl. Akad. Nauk SSSR., 132, 850–852, Chem. Abstr.1961, 55, 5649c.
Wulff G. and Sarhan A. (1972) Ueber die Anwendung von enzymanalog gebauten Polymeren zur Racemattrennung, Angew. Chem. 84, 364.
Wulf G., Lauer M. and Disse B. (1979) Ueber enzymanalog gebaute Polymere X. Ueber die Synthese von Monomeren zur Einfuerung von Aminogruppen in Polymere in definiertem Abstand, Chem. Ber., 112, 2854–2865.
Wulff G., Gross T. and Schoenfeld R. (1997) Enzyme models based on molecularly imprinted polymers with strong esterase activity, Angew. Chem. (Engl.) 36, 1962–1964.
a) Locatelli P., Gamez P. and Lemaire M. (1998) Molecular imprinting of polymerized catalytic complexes in asymmetric catalysis, J. Mol. Catal., 135, 89–98. b) Locatelli P., Gamez P. and Lemaire M. (1998) Molecular imprinting. Polymerised catalytic complexes in asymmetric catalysis, Stud. Surf. Sci. Catal. 108, 517–522.
b) Locatelli P., Gamez P. and Lemaire M. (1998) Molecular imprinting. Polymerised catalytic complexes in asymmetric catalysis, Stud. Surf. Sci. Catal. 108, 517–522.
Gamez P.B., Dunjic B., Pinel C. and Lemaire M. (1995) “Molecular imprinting effect” in the synthesis of immobilized Rhodium complex catalyst, Tetrahedron Lett. 36, 8779–8782.
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KLABUNOVSKII, E., SMITH, G.V., ZSIGMOND, Á. (2006). ASYMMETRIC ADSORPTION ON MINERALS. In: KLABUNOVSKII, E., SMITH, G.V., ZSIGMOND, Á. (eds) HETEROGENEOUS ENANTIOSELECTIVE HYDROGENATION. Catalysis by Metal Complexes, vol 31. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-4296-6_1
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