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Volumn 55, Issue 10, 2001, Pages 831-838

From synthetic methods to γ-peptides -from chemistry to biology

Author keywords

Chiral formyl anion equivalent; Polyhydroxyalkanoates; TADDOL; Peptides; Peptides

Indexed keywords


EID: 0035649110     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (29)

References (83)
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    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
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    • Syntheses of enantiomerically pure compounds (EPC-syntheses)
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
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    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
    • (1983) Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures
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    • 0007243673 scopus 로고
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
    • (1986) EPC Syntheses with C,C Bond Formation via Acetals and Enamines
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    • Stereochemistry of organic and bioorganic transformations
    • Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
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    • Seebach, D.1    Enders, D.2
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    • 0039805469 scopus 로고
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
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    • 0002831079 scopus 로고
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
    • (1979) Chimia , vol.33 , pp. 1
    • Seebach, D.1    Colvin, E.W.2    Lehr, F.3    Weller, T.4
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    • 0001708429 scopus 로고
    • See the articles published in 'Modern Synthetic Methods', Ed. R. Scheffold, Vol. 1-4 (Sauerländer AG, Aarau; Salle + Sauerländer, Frankfurt/Aarau; Salle + Sauerländer, Aarau, and J. Wiley and Sons, New York; Springer Verlag Berlin, Heidelberg, New York, Tokyo), 'Verwendung von Schwefel- und Selenderivaten in der Organischen Synthese' (1976); 'Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses)'; - 'Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?' (1980); 'Titanium and Zirconium Derivatives in Organic Synthesis. A Review with Procedures' (1983); 'EPC Syntheses with C,C Bond Formation via Acetals and Enamines' (1986). For reviews on the use of 3-hydroxycarboxylic acids, of nitroaliphatic compounds, of nitrosamines, and on reactions at temperatures below -75 °C, see D. Seebach, S. Roggo, J. Zimmermann, in 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences Hoechst, Vol. 17, Eds. W. Bartmann, K.B. Sharpless, Verlag Chemie, Weinheim 1987, p. 85; D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1; Angew. Chem. Int. Ed. Engl. 1975, 14, 15; D. Seebach, E.W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1; D. Seebach, A. Hidber, Chimia 1983, 37, 449.
    • (1983) Chimia , vol.37 , pp. 449
    • Seebach, D.1    Hidber, A.2
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    • 0022995478 scopus 로고
    • Pestalotin, Frontalin, Delesserin, Macrostomin, Lycorin, Ophiocarpin, Corlumin, Gloeosporon, Myxovirescin, Pyrenophorin, Grahamimycin, Colletodiol, Conglobatin, Elaiophylin, see the references cited in: D. Seebach, H.-F. Chow, R. F.W. Jackson, M.A. Sutter, S. Thaisrivongs, J. Zimmermann, Liebigs Ann. Chem. 1986, 1281; M.A. Maestro, M. Sefkow, D. Seebach, Liebigs Ann. Chem. 1994, 731.
    • (1986) Liebigs Ann. Chem. , pp. 1281
    • Seebach, D.1    Chow, H.-F.2    Jackson, R.F.W.3    Sutter, M.A.4    Thaisrivongs, S.5    Zimmermann, J.6
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    • Pestalotin, Frontalin, Delesserin, Macrostomin, Lycorin, Ophiocarpin, Corlumin, Gloeosporon, Myxovirescin, Pyrenophorin, Grahamimycin, Colletodiol, Conglobatin, Elaiophylin, see the references cited in: D. Seebach, H.-F. Chow, R. F.W. Jackson, M.A. Sutter, S. Thaisrivongs, J. Zimmermann, Liebigs Ann. Chem. 1986, 1281; M.A. Maestro, M. Sefkow, D. Seebach, Liebigs Ann. Chem. 1994, 731.
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    • Maestro, M.A.1    Sefkow, M.2    Seebach, D.3
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    • NMR and X-ray structures of organolithium compounds, see for instance: D. Seebach, Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624; H. Siegel, Topics in Current Chemistry 1982, 106, 55; J. Heinzer, J.F.M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848; D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308; D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
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    • NMR and X-ray structures of organolithium compounds, see for instance: D. Seebach, Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624; H. Siegel, Topics in Current Chemistry 1982, 106, 55; J. Heinzer, J.F.M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848; D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308; D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
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    • NMR and X-ray structures of organolithium compounds, see for instance: D. Seebach, Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624; H. Siegel, Topics in Current Chemistry 1982, 106, 55; J. Heinzer, J.F.M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848; D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308; D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
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    • NMR and X-ray structures of organolithium compounds, see for instance: D. Seebach, Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624; H. Siegel, Topics in Current Chemistry 1982, 106, 55; J. Heinzer, J.F.M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848; D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308; D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
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    • NMR and X-ray structures of organolithium compounds, see for instance: D. Seebach, Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624; H. Siegel, Topics in Current Chemistry 1982, 106, 55; J. Heinzer, J.F.M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848; D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308; D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
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    • Use of thermophilic microorganisms for synthetic transformations. Role of poly(3-hydroxybutyrate) in biology, biological and pharmacological studies with β-peptides: a) D. Seebach, M.F. Züger, F. Giovannini, B. Sonnleitner, A. Fiechter, Angew. Chem. 1984, 96, 155; Angew. Chem. Int. Ed. Engl. 1984, 23, 151;
    • (1984) Angew. Chem. , vol.96 , pp. 155
    • Seebach, D.1    Züger, M.F.2    Giovannini, F.3    Sonnleitner, B.4    Fiechter, A.5
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    • Use of thermophilic microorganisms for synthetic transformations. Role of poly(3-hydroxybutyrate) in biology, biological and pharmacological studies with β-peptides: a) D. Seebach, M.F. Züger, F. Giovannini, B. Sonnleitner, A. Fiechter, Angew. Chem. 1984, 96, 155; Angew. Chem. Int. Ed. Engl. 1984, 23, 151;
    • (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 151
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    • b) H.-M. Müller, D. Seebach, Angew. Chem. 1993, 105, 483; Angew. Chem. Int. Ed. Engl. 1993, 32, 477;
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    • Catalytic enantioselective reactions from research to application. Diarylmethanol-containing auxiliaries as a study case
    • Spring Meeting of the New Swiss Chemical Society 1997 on Industrial Asymmetric Synthesis: D. Seebach, A.K. Beck, 'Catalytic Enantioselective Reactions from Research to Application. Diarylmethanol-Containing Auxiliaries as a Study Case', Chimia 1997, 51, 293; ILMAC 99, Retrospective/COST Chemistry Symposium: D. Seebach, 'TADDOLs - from Enantioselective Catalysis to Dendritic Cross Linkers to Cholesteric Liquid Crystals', Chimia 2000, 54, 60.
    • (1997) Chimia , vol.51 , pp. 293
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    • TADDOLs -from enantioselective catalysis to dendritic cross linkers to cholesteric liquid crystals
    • Spring Meeting of the New Swiss Chemical Society 1997 on Industrial Asymmetric Synthesis: D. Seebach, A.K. Beck, 'Catalytic Enantioselective Reactions from Research to Application. Diarylmethanol-Containing Auxiliaries as a Study Case', Chimia 1997, 51, 293; ILMAC 99, Retrospective/COST Chemistry Symposium: D. Seebach, 'TADDOLs -from Enantioselective Catalysis to Dendritic Cross Linkers to Cholesteric Liquid Crystals', Chimia 2000, 54, 60.
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    • Excursions of synthetic organic chemists to the world of oligomers and polymers
    • The Academic Polymer Scene in Switzerland, PGS: D. Seebach, A. K. Beck, M. Rueping, J.V. Schreiber, H. Seilner, 'Excursions of Synthetic Organic Chemists to the World of Oligomers and Polymers', Chimia 2001, 55, 98.
    • (2001) Chimia , vol.55 , pp. 98
    • Seebach, D.1    Beck, A.K.2    Rueping, M.3    Schreiber, J.V.4    Seilner, H.5
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    • TADDOLe, ihre derivate und analoga - Vielseitige chirale hilfstoffe
    • a) D. Seebach, A.K. Beck, A. Heckel, 'TADDOLe, ihre Derivate und Analoga - vielseitige chirale Hilfstoffe', Angew. Chem. 2001, 113, 96; Angew. Chem. Int. Ed. 2001, 40, 92;
    • (2001) Angew. Chem. , vol.113 , pp. 96
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    • (2001) Essays in Contemporary Chemistry , pp. 283
    • Seebach, D.1    Beck, A.K.2    Heckel, A.3
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    • From the biopolymer PHB to biological investigations of unnatural β- and γ-peptides
    • Chemical Biology/Biological Chemistry in Switzerland: D. Seebach, M. Albert, P. I. Arvidsson, M. Rueping, J.V. Schreiber, 'From the Biopolymer PHB to Biological Investigations of Unnatural β- and γ-Peptides', Chimia 2001, 55, 345.
    • (2001) Chimia , vol.55 , pp. 345
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    • D. Seebach, J.L. Matthews, 'β-Peptides: a surprise at every turn', Chem. Commun. 1997, 2015; K. Gademann, T. Hintermann, J.V. Schreiber, 'β-Peptides: Twisting and Turning', Curr. Med. Chem. 1999, 6, 905.
    • (1997) Chem. Commun. , pp. 2015
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