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Journal of Biomolecular Structure and Dynamics Volume 7, 1990 - Issue 6

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Original Articles

Critical Main-Chain Length for Conformational Conversion From 3₁₀-Helix to α-Helix in Polypeptides

Vincenzo Pavone Department of Chemistry, University of Naples, 80134, Naples, Italy

Ettore Benedetti Department of Chemistry, University of Naples, 80134, Naples, Italy

Benedetto Di Biasio Department of Chemistry, University of Naples, 80134, Naples, Italy

Carlo Pedone Department of Chemistry, University of Naples, 80134, Naples, Italy

Antonello Santini Department of Chemistry, University of Naples, 80134, Naples, Italy

Alfonso Bavoso Department of Chemistry, University of Basilicata, 85100, Potenza, Italy

Claudio Toniolo Biopolymer Research Center, C.N.R. Department of Organic Chemistry, University of Padova, 35131, Padova, Italy

Marco Crisma Biopolymer Research Center, C.N.R. Department of Organic Chemistry, University of Padova, 35131, Padova, Italy

Luciana Sartore Biopolymer Research Center, C.N.R. Department of Organic Chemistry, University of Padova, 35131, Padova, Italy

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Pages 1321-1331 | Received 15 Nov 1989, Published online: 21 May 2012

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https://doi.org/10.1080/07391102.1990.10508568

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Matthias Rohmer, Jan Freudenberg & Wolfgang Hubertus Binder. (2023) Secondary Structures in Synthetic Poly(Amino Acids): Homo‐ and Copolymers of Poly(Aib), Poly(Glu), and Poly(Asp). Macromolecular Bioscience 23:4.
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Luigi Di Costanzo, Shuchismita DuttaStephen K. Burley. (2018) Amino acid modifications for conformationally constraining naturally occurring and engineered peptide backbones: Insights from the Protein Data Bank. Biopolymers 109:10.
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Giulia Marafon, Marco Crisma & Alessandro Moretto. (2018) Intrinsically Photoswitchable α/β Peptides toward Two-State Foldamers. Angewandte Chemie International Edition 57:32, pages 10217-10220.
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Giulia Marafon, Marco Crisma & Alessandro Moretto. (2018) Intrinsically Photoswitchable α/β Peptides toward Two-State Foldamers. Angewandte Chemie 130:32, pages 10374-10377.
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Giulia Marafon, Ileana Menegazzo, Marta De Zotti, Marco Crisma, Claudio Toniolo & Alessandro Moretto. (2017) Tuning morphological architectures generated through living supramolecular assembly of a helical foldamer end-capped with two complementary nucleobases. Soft Matter 13:23, pages 4231-4240.
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Francesca Biscaglia, Elisa Frezza, Enrico Zurlo & Marina Gobbo. (2016) Linker dependent chirality of solvent induced self-assembled structures of porphyrin–α-helical peptide conjugates. Organic & Biomolecular Chemistry 14:40, pages 9568-9577.
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Marco Crisma, Marta De Zotti, Fernando Formaggio, Cristina Peggion, Alessandro Moretto & Claudio Toniolo. (2015) Handedness preference and switching of peptide helices. Part II: Helices based on noncoded α -amino acids . Journal of Peptide Science 21:3, pages 148-177.
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Edoardo Longo, Karen Wright, Mario Caruso, Emanuela Gatto, Antonio Palleschi, Manuela Scarselli, Maurizio De Crescenzi, Marco Crisma, Fernando Formaggio, Claudio Toniolo & Mariano Venanzi. (2015) Peptide flatlandia: a new-concept peptide for positioning of electroactive probes in proximity to a metal surface. Nanoscale 7:37, pages 15495-15506.
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Shama Tumminakatti, Damodara N. Reddy & Erode N. Prabhakaran. (2015) Exploring the consequences of a representative “disallowed” conformation of Aib on a 3 10 -helical fold . Biopolymers 104:1, pages 21-36.
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Marta De Zotti, Gema Ballano, Micha Jost, Evgeniy S. Salnikov, Burkhard Bechinger, Simona Oancea, Marco Crisma, Claudio Toniolo & Fernando Formaggio. (2014) Solution Synthesis, Conformational Analysis, and Antimicrobial Activity of Three Alamethicin F50/5 Analogs Bearing a Trifluoroacetyl Label. Chemistry & Biodiversity 11:8, pages 1163-1191.
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Fernando Formaggio, Alessandro Moretto, Marco Crisma & Claudio Toniolo. 2013. Peptide Materials. Peptide Materials 359 384 .

Madhvi Gupta Dutta, Puniti Mathur & Virander S Chauhan. (2011) De novo design, synthesis and solution conformational study of two didehydroundecapeptides: effect of nature and number of amino acids interspersed between Phe residues . Journal of Peptide Science 17:12, pages 783-790.
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Edoardo Longo, Alessandro Moretto, Fernando Formaggio & Claudio Toniolo. (2011) The critical main-chain length for helix formation in water: Determined in a peptide series with alternating Aib and Ala residues exclusively and detected with ECD spectroscopy. Chirality 23:9, pages 756-760.
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Hadgu Girmay Gebreslasie, Øyvind Jacobsen & Carl Henrik Görbitz. (2011) N -( tert -Butoxycarbonyl)-α-aminoisobutyryl-α-aminoisobutyric acid methyl ester: two polymorphic forms in the space group P 2 1 / n . Acta Crystallographica Section C Crystal Structure Communications 67:8, pages o283-o287.
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Iria M. Rio-Echevarria, Regina Tavano, Valerio Causin, Emanuele Papini, Fabrizio Mancin & Alessandro Moretto. (2010) Water-Soluble Peptide-Coated Nanoparticles: Control of the Helix Structure and Enhanced Differential Binding to Immune Cells. Journal of the American Chemical Society 133:1, pages 8-11.
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Yosuke Demizu, Mitsunobu Doi, Masaaki Kurihara, Haruhiro Okuda, Masanobu Nagano, Hiroshi Suemune & Masakazu Tanaka. (2011) Conformational studies on peptides containing α,α-disubstituted α-amino acids: chiral cyclic α,α-disubstituted α-amino acid as an α-helical inducer. Organic & Biomolecular Chemistry 9:9, pages 3303.
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Jordi Solà, Madeleine Helliwell & Jonathan Clayden. (2011) Interruption of a 310-helix by a single Gly residue in a poly-Aib motif: A crystallographic study. Biopolymers 95:1, pages 62-69.
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Fernando Formaggio & Claudio Toniolo. (2010) Electronic and vibrational signatures of peptide helical structures: A tribute to Anton Mario Tamburro. Chirality 22:1E, pages E30-E39.
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Naoki Ousaka & Yoshihito Inai. (2008) Transfer of Noncovalent Chiral Information along an Optically Inactive Helical Peptide Chain: Allosteric Control of Asymmetry of the C-Terminal Site by External Molecule that Binds to the N-Terminal Site. The Journal of Organic Chemistry 74:4, pages 1429-1439.
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Alessandro Moretto, Fernando Formaggio, Bernard Kaptein, Quirinus B. Broxterman, Ling Wu, Timothy A. Keiderling & Claudio Toniolo. (2008) First homo-peptides undergoing a reversible 310-helix/α-helix transition: Critical main-chain length. Biopolymers 90:4, pages 567-574.
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Jovencio Hilario, Jan Kubelka & Timothy Keiderling. 2005. Vibrational Spectroscopy of Biological and Polymeric Materials. Vibrational Spectroscopy of Biological and Polymeric Materials 253 324 .

Kazuya Kitagawa, Tomoyuki Morita & Shunsaku Kimura. (2005) A Helical Molecule That Exhibits Two Lengths in Response to an Applied Potential. Angewandte Chemie International Edition 44:39, pages 6330-6333.
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Kazuya Kitagawa, Tomoyuki Morita & Shunsaku Kimura. (2005) A Helical Molecule That Exhibits Two Lengths in Response to an Applied Potential. Angewandte Chemie 117:39, pages 6488-6491.
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Claudio Toniolo, Marco Crisma, Fernando Formaggio, Cristina Peggion, Quirinus Broxterman & Bernard Kaptein. (2005) Peptide β-Bend and 3 10-Helix: from 3D-Structural Studies to Applications as Templates. Journal of Inclusion Phenomena 51:3-4, pages 121-136.
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Subrayashastry Aravinda, Saumen Datta, Narayanaswamy Shamala & Padmanabhan Balaram. (2004) Hydrogen-Bond Lengths in Polypeptide Helices: No Evidence for Short Hydrogen Bonds. Angewandte Chemie International Edition 43:48, pages 6728-6731.
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Claudio Toniolo, Marco Crisma, Fernando Formaggio, Cristina Peggion, Quirinus B. Broxterman & Bernard Kaptein. (2004) Molecular spacers for physicochemical investigations based on novel helical and extended peptide structures. Peptide Science 76:2, pages 162-176.
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Lipika Pal, Pinak Chakrabarti & Gautam Basu. (2003) Sequence and Structure Patterns in Proteins from an Analysis of the Shortest Helices: Implications for Helix Nucleation. Journal of Molecular Biology 326:1, pages 273-291.
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Carlos Alemán, Ana I. Jiménez, Carlos Cativiela, Juan J. Perez & Jordi Casanovas. (2002) Influence of the Phenyl Side Chain on the Conformation of Cyclopropane Analogues of Phenylalanine. The Journal of Physical Chemistry B 106:45, pages 11849-11858.
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Yoshihito Inai & Tadamichi Hirabayashi. (2001) A helical arrangement of ?-substituents of dehydropeptides: Synthesis and conformational study of sequential nona- and dodecapeptides possessing (Z)-?-(1-naphthyl)dehydroalanine residues. Biopolymers 59:5, pages 356-369.
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Igor A. Topol, Stanley K. Burt, Eugen Deretey, Ting-Hua Tang, Andras Perczel, Alexander Rashin & Imre G. Csizmadia. (2001) α- and 3 10 -Helix Interconversion: A Quantum-Chemical Study on Polyalanine Systems in the Gas Phase and in Aqueous Solvent . Journal of the American Chemical Society 123:25, pages 6054-6060.
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Kerstin M�hle, Hans-J�rg Hofmann & Walter Thiel. (2001) Description of peptide and protein secondary structures employing semiempirical methods. Journal of Computational Chemistry 22:5, pages 509-520.
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Kalpana Bhargava & R. Balaji Rao. (2001) Letters in Peptide Science 8:1, pages 41-45.
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Claudio Toniolo, Marco Crisma, Fernando Formaggio & Cristina Peggion. (2001) Control of peptide conformation by the Thorpe-Ingold effect (C?-tetrasubstitution). Biopolymers 60:6, pages 396-419.
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Wen-Ge Han, Marcus Elstner, K. J. Jalkanen, Thomas Frauenheim & S�ndor Suhai. (2000) Hybrid SCC-DFTB/molecular mechanical studies of H-bonded systems and ofN-acetyl-(L-Ala)nN?-methylamide helices in water solution. International Journal of Quantum Chemistry 78:6, pages 459-479.
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Saumen Datta, Manjappara V. Uma, N. Shamala & P. Balaram. (1999) Stereochemistry of Schellman motifs in peptides: Crystal structure of a hexapeptide with a C-terminus 6 ? 1 hydrogen bond. Biopolymers 50:1, pages 13-22.
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Yoshihito Inai, Satoru Ashitaka & Tadamichi Hirabayashi. (1999) A Study of Chain-Length Effect on Helical Screw Sense in Peptides Having an N-Terminal L-Leu Residue. Polymer Journal 31:3, pages 246-253.
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S. Samuelson & G. J. Martyna. (1999) Computer Simulation Studies of Finite Temperature Conformational Equilibrium in Alanine-Based Peptides. The Journal of Physical Chemistry B 103:10, pages 1752-1766.
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Ramesh Kaul & P Balaram. (1999) Stereochemical Control of Peptide Folding. Bioorganic & Medicinal Chemistry 7:1, pages 105-117.
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André Aubry, Daniel Bayeul, Hans Brückner, Norbert Schiemann & Ettore Benedetti. (1998) The crystal state conformation of Aib-rich segments of peptaibol antibiotics. Journal of Peptide Science 4:8, pages 502-510.
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Daniel Obrecht, Michael Altorfer, Udo Bohdal, John Daly, Walter Huber, Alexander Labhardt, Christian Lehmann, Klaus Müller, Ruth Ruffieux, Peter Schönholzer, Clive Spiegler & Cornelia Zumbrunn. (1997) Design and synthesis of novel nonpolar host peptides for the determination of the 310- and α-helix compatibilities of α-amino acid buildig blocks: An assessment of α,α-disubstituted glycines. Biopolymers 42:5, pages 575-626.
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S. Samuelson, D. J. Tobias & G. J. Martyna. (1997) Modern Computational Methodology Applied to the Simulation of Blocked Trialanine Peptide in Vacuo , Water Clusters, and Bulk Water . The Journal of Physical Chemistry B 101:38, pages 7592-7603.
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Carlos Alemán, Ramón Roca, F. Javier Luque & Modesto Orozco. (1997) Helical preferences of alanine, glycine, and aminoisobutyric homopeptides. Proteins: Structure, Function, and Genetics 28:1, pages 83-93.
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Yoshihito Inai, Kazuto Hasegawa, Tadamichi Hirabayashi & Kenji Yokota. (1996) Chain-Length Effects on Helix-Forming Tendency in Sequential Peptides Containing Z-Dehydrophenylalanine Residues. Polymer Journal 28:5, pages 440-445.
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Isabella L. Karle, Arindam Banerjee, Surajit Bhattacharjya & P. Balaram. (1998) Solid state and solution conformations of a helical peptide with a central gly-gly segment. Biopolymers 38:4, pages 515-526.
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Yoshihito Inai, Kazuto Hasegawa, Tadamichi Hirabayashi & Kenji Yokota. (1996) Design of a Helical Backbone. Conformation of Sequential Tridecapeptide Containing Z-Dehydrophenylalanine Residues. Polymer Journal 28:3, pages 238-245.
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I. L. Karle, J. L. Flippen‐Anderson, K. Uma & P. Balaram. (1998) Effects of End Group and Aggregation on Helix Conformation: Crystal Structure of Ac‐(Aib‐Val‐Ala‐Leu) 2 ‐Aib‐ OMe . Journal of Peptide Science 2:2, pages 106-116.
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Fernando Formaggio, Marco Crisma, Claudio Toniolo & Johan Kamphuis. (1998) Solid-state CD and peptide helical screw sense. Biopolymers 38:3, pages 301-304.
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S. Raghothama, M. Chaddha & P. Balaram. (1996) NMR Analysis of a Conformational Transition in an Acyclic Peptide. Model System for Studying Helix Unfolding. The Journal of Physical Chemistry 100:50, pages 19666-19671.
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Paul Hanson, Glenn Millhauser, Fernando Formaggio, Marco Crisma & Claudio Toniolo. (1996) ESR Characterization of Hexameric, Helical Peptides Using Double TOAC Spin Labeling. Journal of the American Chemical Society 118:32, pages 7618-7625.
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Phoebe Xiurong Qi, Robert A. Beckman & A. Joshua Wand. (1996) Solution Structure of Horse Heart Ferricytochrome c and Detection of Redox-Related Structural Changes by High-Resolution 1 H NMR , . Biochemistry 35:38, pages 12275-12286.
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Michel Marraud & André Aubry. (1996) Crystal structures of peptides and modified peptides. Biopolymers 40:1, pages 45-83.
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Adelinda A Yee, Randal Babiuk & Joe D. J O'Neil. (2004) The conformation of an alamethicin in methanol by multinuclear NMR spetroscopy and distance geometry/simulated annealing. Biopolymers 36:6, pages 781-792.
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Wayne R. Fiori & Glenn L. Millhauser. (2004) Exploring the peptide 3 10 ‐helix ⇆ α–helix equilibrium with double label electron spin resonance . Biopolymers 37:4, pages 243-250.
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VANDANA A. BINDRA & ATSUO KUKI. (2009) Conformational preferences of oligopeptides rich in α-aminoisobutyric acid. III. Design, synthesis and hydrogen bonding in 310-helices. International Journal of Peptide and Protein Research 44:6, pages 539-548.
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Isabella L. Karle, Judith L. Flippen‐Anderson, R. Gurunath & P. Balaram. (2008) Facile transition between 3 10 ‐ and α‐helix: Structures of 8‐, 9‐, and 10‐residue peptides containing the ‐(Leu‐Aib‐Ala) 2 ‐Phe‐Aib‐fragment . Protein Science 3:9, pages 1547-1555.
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Critical Main-Chain Length for Conformational Conversion From 3₁₀-Helix to α-Helix in Polypeptides

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Critical Main-Chain Length for Conformational Conversion From 310-Helix to α-Helix in Polypeptides

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Critical Main-Chain Length for Conformational Conversion From 3₁₀-Helix to α-Helix in Polypeptides