Publications 1985-2003

Pre-ETH Publications Karl-Heinz Altmann (1985 – 2003)

K. C. Nicolaou, P. K. Sasmal, G. Rassias, M. V. Reddy, K.-H. Altmann, M. Wartmann, A. O'Brate, P. Giannakakou. Design, synthesis, and biological properties of highly potent epothilone B analogues Angew. Chem. Int. Ed. 2003, 42, 3515-3520.

T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger. The high-resolution solution structure of epothilone A bound to tubulin: An understanding of the structure-activity relationships for a powerful class of antitumor agents. Angew. Chem. Int. Ed. 2003, 115, 2615-2619.

K.-H. Altmann. Epothilone B and its analogs – A new family of anticancer agents. Minirev. Med. Chem. 2003, 3, 149-158. (Invited review)

K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann. The total synthesis and biological assessment of trans-epothilone A. Helv. Chim. Acta 2002, 85, 4086-4110.

K.-H. Altmann, M. J. J. Blommers, G. Caravatti, A. Flörsheimer, K. C. Nicolaou, T. O’Reilly, A. Schmidt, D. Schinzer, M. Wartmann. Synthetic and Semisynthetic Analogs of Epothilones: Chemistry and Biological Activity. In: Anticancer Agents – Frontiers in Cancer Chemotherapy. Ojima, I.; Vite G.D.; Altmann, K.-H., Eds., ACS Symposium Series 796, American Chemical Society, Washington DC, 2001, pp.112-130. (Book chapter)

M. Wartmann, K.-H. Altmann. The Biology and Medicinal Chemistry of Epothilones. Curr. Rev. Med. Chem. – Anticancer Agents 2002, 2, 123-148. (Review)

K. C. Nicolaou, A. Ritzen, K. Namoto, R. M. Buey, J. M. Andreu, M. Wartmann, K.-H. Altmann, A. O’Brate, P. Giannakakou. Chemical synthesis and biological evaluation of novel epothilone B and trans-12,13-cyclopropyl epothilone B analogues. Tetrahedron 2002, 58, 6413-6432.

G. Koch, O. Loiseleur, D. Fuentes, A. Jantsch, K.-H. Altmann. Diastereoselective titanium enolate aldol reaction for the total synthesis of epothilones. Org. Lett. 2002, 4, 3811-3814.

K. C. Nicolaou, K. Namoto, A. Ritzen, T. Ulven, M. Shoji, J. Li, G. D'Amico, D. Liotta, C. T. French, M. Wartmann, K.-H. Altmann, P. Giannakakou. Chemical synthesis and biological evaluation of cis- and trans-12,13-cyclopropyl and 12,13-cyclobutyl epothilones and related pyridine side chain analogues. J. Am. Chem. Soc. 2001, 123, 9313-9323.

K.-H. Altmann. Microtubule-stabilizing agents: a growing class of important anticancer drugs. Curr. Opin. Chem. Biol.  2001, 5, 424-431. (Invited review)

A. Flörsheimer, K.-H. Altmann. Epothilones and their analogues - a new class of promising microtubule inhibitors. Expert Opin. Ther. Pat. 2001, 11, 951-968. (Invited review)

C. J. Wilds, G. Minasov, F. Natt, P. von Matt, K.-H. Altmann, M. Egli. Studies of a Chemically Modified Oligodeoxynucleotide Containing a 5-Atom Amide Backbone which exhibits improved binding to RNA. Nucleosides, Nucleotides & Nucleic Acids  2001,  20, 991-994.

D. Schinzer, K.-H. Altmann, F. Stuhlmann, A. Bauer, M. Wartmann. Synthesis and Biological Evaluation of Aza-epothilones. ChemBioChem 2000, 1, 67-70.

N. End, G. Bold, G. Caravatti, M. Wartmann, K.-H. Altmann. Synthetic epothilone analogs with modifications in the northern hemisphere and the heterocyclic side-chain - synthesis and biological evaluation. Proc. ECSOC-4, 2000, 2000, Meeting Date 2000, 1431-1442.

K. C. Nicolaou, R. Scarpelli, B. Bollbuck, B. Werschkun, M. M. A. Pereira, M. Wartmann, K.-H. Altmann, D. Zaharevitz, R. Gussio, P. Giannakakou. Chemical synthesis and biological properties of pyridine epothilones. Chem. Biol. 2000, 7, 593-599.

K.-H. Altmann, G. Bold, G. Caravatti, N. End, A. Flörsheimer, V. Guagnano, T. O’Reilly, M. Wartmann. Epothilones and their analogs - potential new weapons in the fight against cancer. Chimia 2000, 54, 612 - 621.

K.-H. Altmann, G. Bold, G. Caravatti, A. Flörsheimer, V. Guagnano, M. Wartmann. Synthesis and biological evaluation of highly potent analogues of epothilones B and D.  Bioorg. Med. Chem Lett. 2000, 10, 2765 - 2768.

K.-H. Altmann, M. Wartmann, T. O’Reilly. Epothilones and Related Structures - A new Class of Microtubule Inhibitors with Potent in vivo Antitumor Activity. Biochim. Biphys. Acta 2000, 1470, M79-M71. (Invited review)

G. Bold, K.-H. Altmann, J. Frei, M. Lang, P. W. Manley, P. Traxler, B. Wietfeld, J. Brueggen, E. Buchdunger, R. Cozens, S. Ferrari, P. Furet, F. Hofmann, G. Martiny-

Baron, J. Mestan, J. Rösel, M. Sills, D. Stover, F. Acemoglu, E. Boss, R. Emmenegger, L. Laesser, E. Masso, R. Roth, C. Schlachter, W. Vetterli, D. Wyss, J. M. Wood. New Anilinophthalazines as Potent and Orally Well Absorbed Inhibitors of the VEGF Receptor Tyrosine Kinases Useful as Antagonists of Tumor-Driven Angiogenesis. J. Med. Chem. 2000, 43, 2310.

D. Fabbro, B. P. Monia, K.-H. Altmann, M. Müller, T. Geiger. Inhibition of Tumor Growth by Antisense Oligonucleotides Targeting the Growth Related Protein Kinase c-raf. In: Methods in Molecular Medicine, Vol 35: Gene Therapy of Cancer: Methods and protocols W. Walter, U. Stein, Eds., Humana Press Inc., Totowa, NJ, 1999, pp. 167 - 188. (Book chapter)

P. von Matt, A. De Mesmaeker, U. Pieles, W. Zürcher, K.-H. Altmann. 2-Deoxyribo-PNAs: A Structurally Novel Class of Polyamide Nucleic Acids with Good RNA and DNA binding affinity. Tetrahedron Lett. 1999, 40, 2899-2902.

T. V. Maltseva, K.-H. Altmann, M. Egli, J. Chattopadhyaya. The residence time of the bound water in the hydrophobic minor groove of the carbocyclic-​nucleoside analogs of Dickerson-​Drew dodecamers. J. Biomol. Structure & Dynamics 1998, 16, 569-578.

P. von Matt, R. Kesselring, K.-H. Altmann. An Expeditious Synthesis of 3’-a-Carboxymethyl-2’-O-Methyl Ribonucleosides. Tetrahedron Lett. 1999, 40, 1873-1876.

A. Y. Denisov, E. V. Zamaratski, T. V. Maltseva, A. Sandström, S. Bekiroglu, K.-H. Altmann, M. Egli, J. Chattopadhyaya. The Solution Conformation of a Carbocyclic Analog of the Dickerson-Drew Dodecamer: Comparison with its own X-ray Structure and that of the NMR Structure of the Native Counterpart. J. Biomol. Struct. Dyn. 1998, 16, 547-568.                                                                                                                                

K.-H. Altmann, D. Fabbro, T. Geiger. Antisense and Anti-Gene Therapy in Oncology. In: Advances in DNA Sequence Specific Agents, G. B. Jones, Ed., JAI Pres, 1998, pp. 227 - 266. (Book chapter)

M. Egli, S. Portmann, F. Natt, P. Martin, K.-H. Altmann. Correlating Structure and Stability of DNA Duplexes with Incorporated 2’-O-Modified RNA Analogues. Biochemistry 1998, 30, 10626-10634.

S. M. Freier, K.-H. Altmann. The Ups and Downs of Nucleic Acid Duplex Stability. Nucleic Acids Res. 1997, 25, 4429 - 4443. (Invited Review)

B. Cuenoud, F. Caset, D. Hüsken, F. Natt, R. M. Wolf, K.-H. Altmann, P. Martin, H. E. Moser. Dual Recognition of Double-Stranded DNA by 2'-Aminoethoxy-Modified Oligonucleotides. Angew. Chem. Int. Ed. 1998, 37, 1288 - 1291.

M. Egli, S. Portmann, F. Natt, P. Martin, K.-H. Altmann. Correlating Structure and Stability of DNA Duplexes with Incorporated 2’-O-Modified RNA Analogues. Biochemistry 1998, 30, 10626-10634.

K.-H. Altmann, B. Cuenoud, P. von Matt. Novel Chemistry. In: Applied Antisense Oligonucleotide Technology, A. M. Krieg, C. A. Stein, Eds., Wiley, New York, 1998, pp. 73 -108. (Book chapter)

S. Portmann, K.-H. Altmann, N. Reynes, M. Egli. Crystal Structures of Oligodeoxyribonucleotides Containing 6'-a-Methyl and 6’-a-Hydroxy Carbocyclic Thymidines. J. Am. Chem. Soc. 1997, 119, 2396 - 2403.

K.-H. Altmann, C. Schmit Chiesi, C. Garcia-Echeverria. Polyamide Based Nucleic Acid Analogs ‑ Synthesis of d-Amino Acids with Nucleic Acid Bases Bearing Side Chains. Bioorg. Med. Chem. Lett. 1997, 7, 1119 - 1122.

C. Garcia-Echeverria, C. Schmit Chiesi, D. Hüsken, K.-H. Altmann. Polyamide Based Nucleic Acid Analogs ‑ Synthesis of Oligomers and RNA-Binding Properties. Bioorg. Med. Chem. Lett. 1997, 7, 1123 - 1126.

G. D. Jones, K.-H. Altmann, D. Hüsken, R. T. Walker. Duplex- and Triplex-Forming Properties of 4’-Thio-Modified Oligodeoxynucleotides. Bioorg. Med. Chem. Lett. 1997, 7, 1275 - 1278.   

P. von Matt, T. Lochmann, K.-H. Altmann. Replacement of the Phosphodiester Linkage in Oligonucleotides by Heterocycles: Synthesis of Thymidine Dinucleotide Analogs with Triazole Modified Backbones. Bioorg. Med. Chem. Lett. 1997, 7, 1549 - 1552.

P. von Matt, T. Lochmann, K.-H. Altmann. Replacement of the Phosphodiester Linkage in Oligonucleotides by Heterocycles: The Effect of Triazole- and Imidazole-Modified Backbones on DNA/RNA Duplex Stability. Bioorg. Med. Chem. Lett. 1997, 7, 1553 - 1556.

J. Ammenn, K.-H. Altmann, D. Bellus. Aza-Claisen Rearrangement: Synthesis of 5’-Branched 5’-Aminothymidines. Helv. Chim. Acta 1997, 80, 1589 - 1606.

K.-H. Altmann, P. Martin, N. M. Dean, B. P. Monia. Second Generation Antisense Oligonucleotides - Inhibition of PKC-a and c-raf kinase expression by chimeric oligonucleotides incorporating 6'-substituted carbocyclic nucleotide and 2'-O-ethylene glycol substituted ribonucleotide units. Nucleos. Nucleot. 1997, 16, 917 - 926.

K.-H. Altmann, R. Kesselring, U. Pieles. 6'-Carbon-Substituted Carbocyclic Analogs of 2'-Deoxyribonucleosides - Synthesis and Effect on DNA/RNA Duplex Stability. Tetrahedron 1996, 52, 12699 - 12722.

K.-H. Altmann, M.-O. Bévierre, A. De Mesmaeker, H. E. Moser.  The Evaluation of 2'- and 6'-Substituted Carbocyclic Nucleosides as Building Blocks for Antisense Oligonucleotides. Bioorg. Med. Chem. Lett. 1995, 5, 431 - 436.

A. De Mesmaeker, K.-H. Altmann, A. Waldner, S. Wendeborn. Backbone-modified oligonucleotide analogs and PNA-like structures. Curr. Opin. Struct. Biol. 1995, 5, 343 - 355. (Invited Review)

K.-H. Altmann, R. Kesselring, E. Francotte, G. Rihs. 4',6'-Methano carbocyclic thymidine: a conformationally constrained building block for oligonucleotides. Tetrahedron Lett. 1994, 35, 2331 - 2334.

K.-H. Altmann, S. M. Freier, U. Pieles, T. Winkler. Synthesis of an aza-thymidine and its incorporation into oligonucleotides. Angew. Chem. Int. Ed. Engl. 1994, 33, 1654 - 1657.

K.-H. Altmann, R. Kesselring. The synthesis of 1'-methyl carbocyclic thymidine and its effect on nucleic acid duplex stability. Synlett 1994, 853 - 856.

K.-H. Altmann, R. Imwinkelried, R. Kesselring, G. Rihs. 1',6'-Methano carbocyclic thymidine: synthesis, X-ray crystal structure, and effect on nucleic acid duplex stability. Tetrahedron Lett. 1994, 35, 7625 - 7628.

C. Schmit, M.-O. Bévierre, A. De Mesmaeker, K.-H. Altmann. The Effects of 2'- and 3'-Alkyl Substituents on Oligonucleotide Hybridization and Stability. Bioorg. Med. Chem. Lett. 1994, 4, 1969 - 1974.

K.-H. Altmann. The synthesis of pyrrolidine based analogs of 3'-deoxy thymidine. Tetrahedron Lett. 1993, 34, 7721 - 7724.

K.-H. Altmann, M. Mutter. Die Chemische Synthese von Peptiden und Proteinen. Chem. Unserer Zeit 1993, 27, 274 - 286. (Review)

M. Mutter, G. Tuchscherer, C. Miller, K.-H. Altmann, R. I. Carey, D. F. Wyss, A. M. Labhardt, J. E. Rivier. Template Assembled Synthetic Proteins with Four-Helix-Bundle Topology. Total Chemical Synthesis and Conformational Studies. J. Am. Chem. Soc. 1992, 114, 1463 - 1470.

K.-H. Altmann, E. Altmann, M. Mutter. Conformational Studies on Petides Containing a-Methyl a-Amino Acids. 1. Differential HHelHelix Inducing Potential of (R)- and (S)-2-Methyl Aspartic Acid. Helv. Chim. Acta 1992, 75, 1198 - 1210.

M. Mutter, K.-H. Altmann, R. I. Carey, I. Ernest, R. Flögel, D. Wyss, S. Vuilleumier, J. E. Rivier, G. Tuchscherer. Novel Approaches to Template Assembled Synthetic Proteins. In: Peptides - Structure and Function, Proceedings of the 21st European Peptide Symposium, E. Giralt, D. Andreu, Eds., Escom Science Publishers B. V. 1991, 249 - 250.

R. I. Carey, K.-H. Altmann, M. Mutter. Protein Design: Template Assembled Synthetic Proteins. In: Ciba Foundation Symposium 158 on Host-Guest Molecular Interactions, Wiley, Chichester 1991, 187 - 203.

M. Mutter, R. Gassmann, U. Buttkus, K.-H. Altmann. Switch Peptides: pH-Induced a-Helix to b-Sheet Transitions of Bis-Amphiphilic Peptides. Angew. Chem. Int. Ed. 1991, 30, 1514 - 1516.

K.-H. Altmann, J. Wojcik, M. Vasquez, H. A. Scheraga. Helix-Coil Stability Constants for the Naturally Occurring Amino Acids in Water XXIII. Proline Parameters from Random Poly(hydroxybutyl-L-glutamine-co-L-proline). Biopolymers 1990, 30, 107 - 120 .

J. Wojcik, K.-H. Altmann, H. A. Scheraga. Helix-Coil Stability Constants for the Naturally Occurring Amino Acids in Water XXIV. Half-Cystine Parameters from Random Poly(hydroxybutyl-L‑glutamine-co-S-methylthio-L-cysteine). Biopolymers 1990, 30, 121 - 134.

K.-H. Altmann, H. A. Scheraga. Formation of Local Structures in Bovine Pancreatic Ribonuclease A. Effect of Amino Acid Substitutions on the Preferential Formation of the Native Disulfide Loop in Synthetic Peptides Corresponding to the Amino Acid Sequence Cys 58 - Cys 72 in RNase A. J. Am. Chem. Soc. 1990, 112, 4926 - 4931.

K.-H. Altmann, M. Mutter. A General Strategy for the De Novo Design of Proteins - Template Assembled Synthetic Proteins. Int. J. Biochem. 1990, 22, 947 - 956. (Review)

M. Mutter, K.-H. Altmann, G. Tuchscherer, S. Vuilleumier. Strategies for the De Novo Design of Proteins. Tetrahedron 1988, 44, 771 - 785.

M. Mutter, E. Altmann, K.-H. Altmann, R. Hersperger, P. Koziej, K. Nebel, G. Tuchscherer, S. Vuilleumier, H.-U. Gremlich, K. Müller. The Construction of New Proteins III. Artificial Folding Units by Assembly of Amphiphilic Secondary Structures on a Template. Helv. Chim. Acta 1988, 71, 835 - 847.

E. Altmann, K.-H. Altmann, M. Mutter. Synthesis of Peptides Containing (2S)-2-Methyl Serine. Angew. Chem. Int. Ed. 1988, 27, 858 - 859.

E. Altmann, K.-H. Altmann, K. Nebel, M. Mutter. Conformational Studies on Host-Guest Peptides containing a-Methyl a-Amino Acids -  Comparison of the Helix-Inducing Potential of a-Amino Isobutyric Acid, (2S)-2-Ethyl Alanine, and (2S)-2-Methyl Serine. Int. J. Pept. Protein Res. 1988, 32, 344 - 349.

M. Mutter, K.-H. Altmann, H. Gehrhardt. Functionalized Polyethylene Glycols and Polypeptides in Organic Synthesis and Catalysis. Reactive Polymers 1987, 6, 99 - 107.

M. Mutter, K.-H. Altmann, T. Vorherr, S. Vuilleumier. The construction of new proteins - design, synthesis and conformational properties of polypeptides with bab-​topology. Peptides - Structure and Function, Proceedings of the 19th European Peptide Symposium, D. Theodoropoulos, Ed., de Gruyter, Berlin 1987, 307 - 310.

T. Vorherr, K.-H. Altmann, M. Mutter. Single-Centre Model for the Active Site of a-Chymotrypsin. Helv. Chim. Acta 1986, 69, 410 - 414.

M. Mutter, K.-H. Altmann, A. Flörsheimer, J. Herbert. Sequence-Dependence of Secondary Structure Formation IV: Helix-Forming Potential of Amphiphilic Oligopeptides containing Aib Residues. Helv. Chim. Acta 1986, 69, 786 -792.

K.-H. Altmann, A. Flörsheimer, M. Mutter. Sequence-Dependence of Secondary Structure Formation III: b-structure forming potential of amphiphilic oligopeptides containing alternating L-Val-L-Thr and L-Leu-L-Ser residues. Int. J. Pept. Protein Res. 1986, 27, 314 - 319.

M. Mutter, K.-H. Altmann, K. Müller, S. Vuilleumier, T. Vorherr. Approaches to Synthetic Vaccines. Design of Epitope-Containing Amphiphilic Peptides Matching the Antigenic Structure in the Native Protein. Helv. Chim. Acta 1986, 69, 985 - 995.

M. Mutter, K.-H. Altmann, T. Vorherr. The Construction of New Proteins II. Design, Synthesis and Conformational Studies of Folding Units with bab-Topology. Z. Naturforsch. 1986, 41b, 1315 - 1322.    

M. Mutter, K.-H. Altmann. The Construction of New Proteins. Angew. Makromol. Chem. 1986, 145/146, 211 - 229. (Review)

M. Mutter, K.-H. Altmann, D. Bellof, A. Flörsheimer, J. Herbert, M. Huber, B. Klein, L. Strauch, T. Vorherr, H.-U. Gremlich. Impact of secondary structure formation in peptide synthesis. Peptides - Structure and Function, Proceedings of the 9th American Peptide Symposium, C. M. Deber, V. J. Hruby, K. D. Kopple, Eds., Pierce Chemical Company, Rockford Ill 1985, 397 - 405.

M. Mutter, K.-H.Altmann. Sequence-Dependence of Secondary Structure Formation II: Effect of nearest neighbour interactions on the b-structure formation of host-guest peptides. Int. J. Pept. Protein Res. 1985, 26, 373 – 380.

M. Mutter, K.-H. Altmann, J. Schmitt. Poly(ethylene glycol)-bound peptides as single centre models for enzyme-like catalysis. Makromol. Chem., Rapid Commun. 1985, 6, 785 - 789.

M. Mutter, F. Maser, K.-H. Altmann, C. Toniolo, G. M. Bonora. Sequence-Dependence of Secondary Structure Formation: Conformational Studies of Host-Guest Peptides in a-Helix and b-Structure Supporting Media. Biopolymers 1985, 24, 1057 - 1074.