Title: Screw‐Sense Control of Helical Oligopeptides Containing Equal Amounts of <scp>L</scp>‐ and <scp>D</scp>‐Amino Acids
Abstract: Chemistry – A European JournalVolume 17, Issue 40 p. 11107-11109 Communication Screw-Sense Control of Helical Oligopeptides Containing Equal Amounts of L- and D-Amino Acids Dr. Yosuke Demizu, Corresponding Author Dr. Yosuke Demizu [email protected] Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorProf. Mitsunobu Doi, Prof. Mitsunobu Doi Osaka University of Pharmaceutical Sciences, Osaka 569-1094 (Japan)Search for more papers by this authorYukiko Sato, Yukiko Sato Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorProf. Masakazu Tanaka, Prof. Masakazu Tanaka Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521 (Japan)Search for more papers by this authorDr. Haruhiro Okuda, Dr. Haruhiro Okuda Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorDr. Masaaki Kurihara, Corresponding Author Dr. Masaaki Kurihara [email protected] Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this author Dr. Yosuke Demizu, Corresponding Author Dr. Yosuke Demizu [email protected] Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorProf. Mitsunobu Doi, Prof. Mitsunobu Doi Osaka University of Pharmaceutical Sciences, Osaka 569-1094 (Japan)Search for more papers by this authorYukiko Sato, Yukiko Sato Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorProf. Masakazu Tanaka, Prof. Masakazu Tanaka Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521 (Japan)Search for more papers by this authorDr. Haruhiro Okuda, Dr. Haruhiro Okuda Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this authorDr. Masaaki Kurihara, Corresponding Author Dr. Masaaki Kurihara [email protected] Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501 (Japan), Fax: (+81) 3-3707-6950Search for more papers by this author First published: 23 August 2011 https://doi.org/10.1002/chem.201101809Citations: 26Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Residue order is important! The preferred secondary structures of Boc-(L-Leu-D-Leu-Aib)n-OMe containing equal amounts of L- and D-Leu have been investigated and the results show that these residues form right-handed (P) α helices in both solution and crystalline states (see picture). Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201101809_sm_miscellaneous_information.pdf398.5 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1C. Branden, J. Tooze, Introduction to Protein Structure, Garland, New York, 1991, pp. 1–31. 2 2aG. Bunkóczi, L. Vertesy, G. M. Sheldrick, Angew. Chem. 2005, 117, 1364–1366; Angew. Chem. Int. Ed. 2005, 44, 1340–1342; 2bL. E. Townsley, A. Tucker, S. Sham, J. F. Hinton, Biochemistry 2001, 40, 11676–11686; 2cB. M. Burkhart, R. M. Gassman, D. A. Langs, W. A. Pangborn, W. L. Duax, Biophys. J. 1998, 75, 2135–2146; 2dD. A. Langs, Science 1988, 241, 188–191. 3 3aM. Crisma, F. Formaggio, M. Pantano, G. Valle, G. M. Bonora, C. Toniolo, H. E. Schoemaker, J. Kamphuis, J. Chem. Soc. Perkin Trans. 2 1994, 1735–1742; 3bB. Di Blasio, E. Benedetti, V. Pavone, C. Pedone, G. Cristoph, G. P. Lorenzi, Biopolymers 1989, 28, 203–214; 3cB. Di Blasio, E. Benedetti, V. Pavone, C. Pedone, O. Spiniello, G. P. Lorenzi, Biopolymers 1989, 28, 193–201; 3dF. G. Fick, J. Semen, H. G. Elias, Makromol. Chem. 1978, 179, 579–590; 3eE. Benedetti, B. Di Blasio, C. Pedone, G. P. Lorenzi, L. Tomasic, V. 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Sci. 2011, 17, 420–426. 7Recently, we have reported that unique peptide structures, such as 310-helix, hairpin, and S-shape turn can be built by permutation of two L-Leu, two D-Leu, and two Aib residues in hexapeptides; Y. Demizu, M. Doi, Y. Sato, M. Tanaka, H. Okuda, M. Kurihara, J. Org. Chem. 2010, 75, 5234–5239. 8 8aM. Nagano, M. Doi, M. Kurihara, H. Suemune, M. Tanaka, Org. Lett. 2010, 12, 3564–3566; 8bJ. Sheehan, P. Cruickshank, G. Boshart, J. Org. Chem. 1961, 26, 2525–2528; 8cJ. Sheehan, G. P. Hess, J. Am. Chem. Soc. 1955, 77, 1067–1068. 9Y. Demizu, M. Tanaka, M. Nagano, M. Kurihara, M. Doi, T. Maruyama, H. Suemune, Chem. Pharm. Bull. 2007, 55, 840–842. 10 10aF. Formaggio, M. Crisma, P. Rossi, P. Scrimin, B. Kaptein, Q. B. Broxterman, J. Kamphuis, C. Toniolo, Chem. Eur. J. 2000, 6, 4498–4504; 10bC. Toniolo, A. Polese, F. Formaggio, M. Crisma, J. Kamphuis, J. Am. Chem. Soc. 1996, 118, 2744–2745. 11M. Tanaka, Y. Demizu, M. Doi, M. Kurihara, H. Suemune, Angew. Chem. 2004, 116, 5474–5477; Angew. Chem. Int. Ed. 2004, 43, 5360–5363. 12CCDC-798452 (1) and 815427 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via: www.ccdc.cam.ac.uk/data_request/cif. Crystal data: 1: C54H101O13N9, Mr=1084.44, space group P21, a=11.493, b=20.119, c=14.627 Å, β=90.154°, V=3382.1 Å3, Z=2, T=240 K, μ(MoKα)=0.76 cm−1, no. of observations=4309 (I>2σ(I)), no. of variables=686, R1=0.1138, Rw=0.2709; 2: C70H128O15N12.2.48(C4H8O2).2H2O, Mr=1632.38, space group P212121, a=14.972, b=16.234, c=38.546 Å, V=9368.8 Å3, Z=4, T=240 K, μ(MoKα)=0.84 cm−1, no. of observations=20643 (I>2σ(I)), no. of variables=1183, R1=0.683, Rw=0.1881. 13See the Supporting Information for torsion angles, hydrogen-bond parameters, and ORTEP drawings. 14 14aH. A. Nagarajaram, R. Sowdhamini, C. Ramakrishnan, P. Balaram, FEBS Lett. 1993, 321, 79–83; 14bC. Schellman in Protein Folding: Conference Proceedings (Ed.: ), Elsevier, New York, 1980, pp. 53–61. 15 15aS. Aravinda, N. Shamala, A. Bandyopadhyay, P. Balaram, J. Am. Chem. Soc. 2003, 125, 15065–15075; 15bI. L. Karle, J. L. Flippen-Anderson, K. Uma, P. Balaram, Int. J. Pept. Protein Res. 1993, 42, 401–410. 16The side-chains of the L-Leu(1), D-Leu(2), and D-Leu(5) residues and the 1,4-dioxane molecules were disordered. 17R.-P. Hummel, C. Toniolo, G. Jung, Angew. Chem. 1987, 99, 1180–1182; Angew. Chem. Int. Ed. Engl. 1987, 26, 1150–1152. Citing Literature Volume17, Issue40September 26, 2011Pages 11107-11109 ReferencesRelatedInformation
Publication Year: 2011
Publication Date: 2011-08-23
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 26
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