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Volumn 34, Issue 1-2, 2004, Pages 79-92

Chiral amplification of oligopeptides via polymerization in two-dimensional crystallites on water

Author keywords

Biomolecular handedness; Chiral amplification; Grazing incidence X ray diffraction; Homochiral oligopeptides; Lattice controlled polymerization; Self assembled 2 D crystallites

Indexed keywords

BIOPOLYMER; OLIGOPEPTIDE; WATER;

EID: 0842264159     PISSN: 01696149     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:ORIG.0000009830.40297.fe     Document Type: Conference Paper
Times cited : (21)

References (28)
  • 1
    • 0018457750 scopus 로고
    • Photopolymerizarion in Chiral Crystals. 3. Toward an 'Absolute' Asymmetric Synthesis of Optically Active Dimers and Polymers with Quantitative Enantiomeric Yield
    • Addadi, L. and Lahav, M.: 1979, Photopolymerizarion in Chiral Crystals. 3. Toward an 'Absolute' Asymmetric Synthesis of Optically Active Dimers and Polymers with Quantitative Enantiomeric Yield, J. Am. Chem. Soc. 10, 2152-2156.
    • (1979) J. Am. Chem. Soc. , vol.10 , pp. 2152-2156
    • Addadi, L.1    Lahav, M.2
  • 2
    • 0842298971 scopus 로고
    • Spontaneous Asymmetric Transformations in Chiral and Centrosymmetric Single Crystals
    • Addadi, L., van Mil, J., Berkovitch-Yellin, Z., Leiserowitz, L. and Lahav, M.: 1985, Spontaneous Asymmetric Transformations in Chiral and Centrosymmetric Single Crystals, Chemica Scripta 25, 91-99.
    • (1985) Chemica Scripta , vol.25 , pp. 91-99
    • Addadi, L.1    Van Mil, J.2    Berkovitch-Yellin, Z.3    Leiserowitz, L.4    Lahav, M.5
  • 3
    • 0001283767 scopus 로고
    • Stereochemistry and Molecular Recognition in Two Dimensions
    • Arnett, E. M., Harvay, N. G. and Rose P. L.: 1989, Stereochemistry and Molecular Recognition in Two Dimensions, Acc. Chem. Res. 22, 131-138.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 131-138
    • Arnett, E.M.1    Harvay, N.G.2    Rose, P.L.3
  • 4
    • 0033921344 scopus 로고    scopus 로고
    • Kinetic Aspects of Nonlinear Effects in Asymmetric Catalysis
    • Blackmond, D.: 2000, Kinetic Aspects of Nonlinear Effects in Asymmetric Catalysis, Acc. Chem. Res. 33, 402-411.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 402-411
    • Blackmond, D.1
  • 5
    • 0035050335 scopus 로고    scopus 로고
    • Stereoselectivity in the Oligomerization of Racemic Tryptophan N-Carboxyanhydride (NCA-Trp) as Determined by Isotope Labeling and Mass Spectrometry
    • Blocher, M., Hitz, T. Luisi and P. L.: 2001, Stereoselectivity in the Oligomerization of Racemic Tryptophan N-Carboxyanhydride (NCA-Trp) as Determined by Isotope Labeling and Mass Spectrometry, Helv. Chim. Acta 84, 842-847.
    • (2001) Helv. Chim. Acta , vol.84 , pp. 842-847
    • Blocher, M.1    Hitz, T.L.2    Luisi, P.L.3
  • 6
    • 0030621130 scopus 로고    scopus 로고
    • Enantiomeric Excesses in Meteoritic Amino Acids
    • Cronin, J. R. and Pizzarelo, S.: 1997, Enantiomeric Excesses in Meteoritic Amino Acids, Science 275, 951-955.
    • (1997) Science , vol.275 , pp. 951-955
    • Cronin, J.R.1    Pizzarelo, S.2
  • 7
    • 0030741176 scopus 로고    scopus 로고
    • The First Living Systems: A Bioenergetic Perspective
    • Deamer, D. W.: 1997, The First Living Systems: A Bioenergetic Perspective, Microb. Mol. Biol. Rev. 61, 239-261.
    • (1997) Microb. Mol. Biol. Rev. , vol.61 , pp. 239-261
    • Deamer, D.W.1
  • 8
    • 0017782857 scopus 로고
    • Asymmetric Photolysis of (R, S)-leucine-with Circularly Polarized Ultraviolet Light
    • Flores, J. J., Bonner, W. A, and Massay, G. A.: 1977, Asymmetric Photolysis of (R, S)-leucine-with Circularly Polarized Ultraviolet Light, J. Am. Chem. Soc. 99, 3622-3625.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 3622-3625
    • Flores, J.J.1    Bonner, W.A.2    Massay, G.A.3
  • 9
    • 0034310742 scopus 로고    scopus 로고
    • Spontaneous Formation of Polypetides in the Interfacial Thin Films of Amphiphilic Amino Acid Esters: Acceleration of the Polycondensation and Control of the Structure of Resultant Polymers
    • Fukuda, K., Shibasaki, Y., Nakahara, H. and Liu M.: 2000, Spontaneous Formation of Polypetides in the Interfacial Thin Films of Amphiphilic Amino Acid Esters: Acceleration of the Polycondensation and Control of the Structure of Resultant Polymers, Adv. Colloid. Interface Science 87, 113-145.
    • (2000) Adv. Colloid. Interface Science , vol.87 , pp. 113-145
    • Fukuda, K.1    Shibasaki, Y.2    Nakahara, H.3    Liu, M.4
  • 10
    • 0032538773 scopus 로고    scopus 로고
    • Non-Linear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation
    • Girard, C. and Kagan, H. B.: 1998, Non-Linear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation, Angew. Chem. Int. Ed. 37, 2923-2959.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2923-2959
    • Girard, C.1    Kagan, H.B.2
  • 12
    • 0035354582 scopus 로고    scopus 로고
    • Design and Characterization of Crystalline Thin Film Architectures at the Air-Liquid Interface: Simplicity to Complexity
    • Kuzmenko, I., Rapaport, H., Kjaer, K., Als-Nielsen J., Weissbuch, I., Lahav, M. and Leiserowitz, L.: 2001, Design and Characterization of Crystalline Thin Film Architectures at the Air-Liquid Interface: Simplicity to Complexity, Chem. Rev. 101, 1659-1696.
    • (2001) Chem. Rev. , vol.101 , pp. 1659-1696
    • Kuzmenko, I.1    Rapaport, H.2    Kjaer, K.3    Als-Nielsen, J.4    Weissbuch, I.5    Lahav, M.6    Leiserowitz, L.7
  • 13
    • 0000305354 scopus 로고
    • A New Method of Enantiomeric Purification via a Topochemical Photodimerization Reaction. Application to Three 1-Aryl Ethanols
    • Lahav, M., Laub, F., Gati, E., Leiserowitz, L. and Ludmer, Z.: 1976, A New Method of Enantiomeric Purification via a Topochemical Photodimerization Reaction. Application to Three 1-Aryl Ethanols, J. Am. Chem. Soc. 98, 1620-1622.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 1620-1622
    • Lahav, M.1    Laub, F.2    Gati, E.3    Leiserowitz, L.4    Ludmer, Z.5
  • 14
    • 0038583868 scopus 로고    scopus 로고
    • Generation of Oligopeptides of Homochiral Sequence via Topochemical Reactions within Racemic Crystals of Phenylalanine-N-Carboxyanhydride
    • Nery, J. G., Bolbach, G., Weissbuch, I. and Lahav, M.: 2003, Generation of Oligopeptides of Homochiral Sequence via Topochemical Reactions within Racemic Crystals of Phenylalanine-N-Carboxyanhydride, Angew. Chem. Int. Ed. 42, 2157-2161.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2157-2161
    • Nery, J.G.1    Bolbach, G.2    Weissbuch, I.3    Lahav, M.4
  • 15
    • 0346752024 scopus 로고    scopus 로고
    • Amphiphilic Homochiral Oligopeptides Generated via Phase Separation of Non-Racemic α-Amino Acid Derivatives and Lattice-Controlled Polycondensation in a Phospholipid Environment
    • in press
    • Rubinstein, I., Bolbach, G., Weygand, M. J., Kjaer, K., Weissbuch, I. and Lahav, M.: 2003, Amphiphilic Homochiral Oligopeptides Generated via Phase Separation of Non-Racemic α-Amino Acid Derivatives and Lattice-Controlled Polycondensation in a Phospholipid Environment, Helv. Chim. Acta (in press).
    • (2003) Helv. Chim. Acta
    • Rubinstein, I.1    Bolbach, G.2    Weygand, M.J.3    Kjaer, K.4    Weissbuch, I.5    Lahav, M.6
  • 17
    • 0037455228 scopus 로고    scopus 로고
    • Amplification of chirality from extremely low to greater than 99.5% ee by asymmetric autocatalysis
    • Sato, I., Urabe, H., Ishiguro, S., Shibata, T. and Soai, K.: 2003, Amplification of chirality from extremely low to greater than 99.5% ee by asymmetric autocatalysis, Angew. Chem. Int. Ed. 42, 315-317.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 315-317
    • Sato, I.1    Urabe, H.2    Ishiguro, S.3    Shibata, T.4    Soai, K.5
  • 18
    • 0026237586 scopus 로고
    • Polymerization and Conformation of N-Carboxy Anhydrides of a L-Glutamic Acid Derivative in Monolayers
    • Shibata, A. Hashimura, Y., Yamashita, S., Ueno, S. and Yamashita, T.: 1991, Polymerization and Conformation of N-Carboxy Anhydrides of a L-Glutamic Acid Derivative in Monolayers, Langmuir 7, 2261-2265.
    • (1991) Langmuir , vol.7 , pp. 2261-2265
    • Shibata, A.1    Hashimura, Y.2    Yamashita, S.3    Ueno, S.4    Yamashita, T.5
  • 19
    • 0037190060 scopus 로고    scopus 로고
    • Enantioselective Synthesis without Discrete Optically Active Additives
    • Singleton, D. A. and Vo, L. K.: 2002, Enantioselective Synthesis without Discrete Optically Active Additives, J. Am. Chem. Soc. 124, 10010-10011.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10010-10011
    • Singleton, D.A.1    Vo, L.K.2
  • 20
    • 0033623873 scopus 로고    scopus 로고
    • Enantioselective Automultiplication of Chiral Molecules by Asymmetric Autocatalysis
    • Soai, K., Shibata, T. and Sato I.: 2000, Enantioselective Automultiplication of Chiral Molecules by Asymmetric Autocatalysis, Acc. Chem. Res. 33, 382-390.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 382-390
    • Soai, K.1    Shibata, T.2    Sato, I.3
  • 21
    • 84989527574 scopus 로고
    • Structured Self-Aggregates of 4-Methoxy-(E)-Cinnamic Acid at the Air/Solution Interface as Detected by 2π-2π Photodimerization and their Role in the Control of Crystal Polymorphism
    • Weissbuch, I., Leiserowitz, L. and Lahav, M.: 1991, Structured Self-Aggregates of 4-Methoxy-(E)-Cinnamic Acid at the Air/Solution Interface as Detected by 2π-2π Photodimerization and their Role in the Control of Crystal Polymorphism J. Am. Chem. Soc. 113, 8941-8943.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8941-8943
    • Weissbuch, I.1    Leiserowitz, L.2    Lahav, M.3
  • 22
    • 0040816360 scopus 로고
    • Application of Cryo-Electron Microscopy to Self-Assembled Mixed Monolayers for Studying Crystalinity and Twinning
    • Weissbuch, I., Majewski, J., Margulis, L., Lahav, M. and Leiserowitz, L: 1993, Application of Cryo-Electron Microscopy to Self-Assembled Mixed Monolayers for Studying Crystalinity and Twinning, J. Phys. Chem. 97, 8692-8694.
    • (1993) J. Phys. Chem. , vol.97 , pp. 8692-8694
    • Weissbuch, I.1    Majewski, J.2    Margulis, L.3    Lahav, M.4    Leiserowitz, L.5
  • 23
    • 84955381144 scopus 로고
    • Lock-and-Key Processes at Crystalline Interfaces: Relevance to the Spontaneous Generation of Chirality
    • Behr, J.-P. (ed.), John Wiley & Sons Ltd, New York
    • Weissbuch, I., Popovitz-Biro, R., Leiserowitz, L. and Lahav, M.: 1994 Lock-and-Key Processes at Crystalline Interfaces: Relevance to the Spontaneous Generation of Chirality in Behr, J.-P. (ed.), The Lock and Key Principle, John Wiley & Sons Ltd, New York, pp. 173-246.
    • (1994) The Lock and Key Principle , pp. 173-246
    • Weissbuch, I.1    Popovitz-Biro, R.2    Leiserowitz, L.3    Lahav, M.4
  • 24
    • 0031025230 scopus 로고    scopus 로고
    • Separation of Enantiomers and Racemate Formation in Two-Dimensional Crystals at the Water Surface from Racemic a-Amino Acid Amphiphiles: Design and Structure
    • Weissbuch, I., Berfeld, M., Bouwman, W., Kjaer, K., Als-Nielsen, J., Lahav, M. and Leiserowitz, L.: 1997, Separation of Enantiomers and Racemate Formation in Two-Dimensional Crystals at the Water Surface from Racemic a-Amino Acid Amphiphiles: Design and Structure, J. Am. Chem. Soc. 119, 933-942.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 933-942
    • Weissbuch, I.1    Berfeld, M.2    Bouwman, W.3    Kjaer, K.4    Als-Nielsen, J.5    Lahav, M.6    Leiserowitz, L.7
  • 25
    • 0037036724 scopus 로고    scopus 로고
    • Oligopeptides with Homochiral Sequences Generated from Racemic Precursors that Spontaneously Separate into Enantiomorphous Two-Dimensional Crystalline Domains on Water Surface
    • Weissbuch, I., Bolbach, G., Zepik, H., Shavit, E., Tang, M., Frey, J., Jensen, T. R., Kjaer, K., Leiserowitz, L. and Lahav, M.: 2002, Oligopeptides with Homochiral Sequences Generated from Racemic Precursors that Spontaneously Separate into Enantiomorphous Two-Dimensional Crystalline Domains on Water Surface, J. Am. Chem. Soc. 124, 9093-9104.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9093-9104
    • Weissbuch, I.1    Bolbach, G.2    Zepik, H.3    Shavit, E.4    Tang, M.5    Frey, J.6    Jensen, T.R.7    Kjaer, K.8    Leiserowitz, L.9    Lahav, M.10
  • 26
    • 0038669338 scopus 로고    scopus 로고
    • Homochiral Oligopeptides by Chiral Amplification within Two-Dimensional Crystalline Self-Assemblies at the Air-Water Interface; Relevance to Biomolecular Handedness
    • Weissbuch, I., Zepik, H., Bolbach, G., Shavit, E., Tang, M., Jensen, T. R., Kjaer, K., Leiserowitz, L. and Lahav, M.: 2003a, Homochiral Oligopeptides by Chiral Amplification within Two-Dimensional Crystalline Self-Assemblies at the Air-Water Interface; Relevance to Biomolecular Handedness, Chem. Eur. J. 9, 1782-1794.
    • (2003) Chem. Eur. J. , vol.9 , pp. 1782-1794
    • Weissbuch, I.1    Zepik, H.2    Bolbach, G.3    Shavit, E.4    Tang, M.5    Jensen, T.R.6    Kjaer, K.7    Leiserowitz, L.8    Lahav, M.9
  • 27
    • 0347382351 scopus 로고    scopus 로고
    • Crystalline Phase Separation of Racemic and Non-Racemic Zwitterionic α-Amino Acid Amphiphiles in a Phospholipid Environment at the Air-Water Interface; a Grazing Incidence X-ray Diffraction Study
    • in press
    • Weissbuch, I., Rubinstein, I., Weygand, M. J., Kjaer, K., Leiserowitz, L. and Lahav, M.: 2003b, Crystalline Phase Separation of Racemic and Non-Racemic Zwitterionic α-Amino Acid Amphiphiles in a Phospholipid Environment at the Air-Water Interface; A Grazing Incidence X-ray Diffraction Study, Helv. Chim. Acta (in press).
    • (2003) Helv. Chim. Acta
    • Weissbuch, I.1    Rubinstein, I.2    Weygand, M.J.3    Kjaer, K.4    Leiserowitz, L.5    Lahav, M.6


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