Sugar‐Modified Foldamers as Conformationally Defined and Biologically Distinct Glycopeptide Mimics
2013; Wiley; Volume: 52; Issue: 39 Linguagem: Inglês
10.1002/anie.201304239
ISSN1521-3773
AutoresAloysius Siriwardena, Kiran Kumar Pulukuri, Pancham S. Kandiyal, Saumya Roy, Omprakash Bande, Subhash Chandra Ghosh, José M. Garcı́a Fernández, Fernando A. Martín, Jean‐Marc Ghigo, Christophe Beloin, Keigo Ito, Robert J. Woods, Ravi Sankar Ampapathi⧧, Tushar Kanti Chakraborty,
Tópico(s)Click Chemistry and Applications
ResumoAngewandte Chemie International EditionVolume 52, Issue 39 p. 10221-10226 Communication Sugar-Modified Foldamers as Conformationally Defined and Biologically Distinct Glycopeptide Mimics† Dr. Aloysius Siriwardena, Corresponding Author Dr. Aloysius Siriwardena aloysius.siriwardena@u-picardie.fr Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorKiran Kumar Pulukuri, Kiran Kumar Pulukuri Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorPancham S. Kandiyal, Pancham S. Kandiyal Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India)Search for more papers by this authorDr. Saumya Roy, Dr. Saumya Roy Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France)Search for more papers by this authorDr. Omprakash Bande, Dr. Omprakash Bande Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France)Search for more papers by this authorDr. Subhash Ghosh, Dr. Subhash Ghosh Organic Chemistry Division III, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007 (India)Search for more papers by this authorDr. José Manuel Garcia Fernández, Dr. José Manuel Garcia Fernández Instituto de Investigaciones, Quìmicas(IIQ), CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092 Sevilla (Spain)Search for more papers by this authorDr. Fernando Ariel Martin, Dr. Fernando Ariel Martin Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Jean-Marc Ghigo, Dr. Jean-Marc Ghigo Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Christophe Beloin, Dr. Christophe Beloin Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Keigo Ito, Dr. Keigo Ito The Complex Carbohydrate Research Center, The Department of Biochemistry and Molecular Biology, The University of Georgia, Athens, 30602 GA (USA)Search for more papers by this authorDr. Robert J. Woods, Dr. Robert J. Woods The Complex Carbohydrate Research Center, The Department of Biochemistry and Molecular Biology, The University of Georgia, Athens, 30602 GA (USA) The School of Chemistry, National University of Ireland, Galway, University Road, Galway (Ireland)Search for more papers by this authorDr. Ravi Sankar Ampapathi, Corresponding Author Dr. Ravi Sankar Ampapathi ravi_sa@cdri.res.in Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorDr. Tushar Kanti Chakraborty, Corresponding Author Dr. Tushar Kanti Chakraborty chakraborty@cdri.res.in Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this author Dr. Aloysius Siriwardena, Corresponding Author Dr. Aloysius Siriwardena aloysius.siriwardena@u-picardie.fr Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorKiran Kumar Pulukuri, Kiran Kumar Pulukuri Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorPancham S. Kandiyal, Pancham S. Kandiyal Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India)Search for more papers by this authorDr. Saumya Roy, Dr. Saumya Roy Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France)Search for more papers by this authorDr. Omprakash Bande, Dr. Omprakash Bande Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France)Search for more papers by this authorDr. Subhash Ghosh, Dr. Subhash Ghosh Organic Chemistry Division III, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007 (India)Search for more papers by this authorDr. José Manuel Garcia Fernández, Dr. José Manuel Garcia Fernández Instituto de Investigaciones, Quìmicas(IIQ), CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092 Sevilla (Spain)Search for more papers by this authorDr. Fernando Ariel Martin, Dr. Fernando Ariel Martin Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Jean-Marc Ghigo, Dr. Jean-Marc Ghigo Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Christophe Beloin, Dr. Christophe Beloin Institut Pasteur, Unité de Génétique des Biofilms, 25 rue du Dr. Roux, 75724 Paris cedex 15 (France)Search for more papers by this authorDr. Keigo Ito, Dr. Keigo Ito The Complex Carbohydrate Research Center, The Department of Biochemistry and Molecular Biology, The University of Georgia, Athens, 30602 GA (USA)Search for more papers by this authorDr. Robert J. Woods, Dr. Robert J. Woods The Complex Carbohydrate Research Center, The Department of Biochemistry and Molecular Biology, The University of Georgia, Athens, 30602 GA (USA) The School of Chemistry, National University of Ireland, Galway, University Road, Galway (Ireland)Search for more papers by this authorDr. Ravi Sankar Ampapathi, Corresponding Author Dr. Ravi Sankar Ampapathi ravi_sa@cdri.res.in Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this authorDr. Tushar Kanti Chakraborty, Corresponding Author Dr. Tushar Kanti Chakraborty chakraborty@cdri.res.in Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India) Aloysius Siriwardena, Laboratoiredes Glucides, FRE-3517, Université de Picardie Jules Verne, Amiens 80039 (France) Ravi Sankar Ampapathi, Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute (India), Lucknow 226031 (India) Tushar Kanti Chakraborty, Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031 (India)Search for more papers by this author First published: 13 August 2013 https://doi.org/10.1002/anie.201304239Citations: 24 † T.K.C., R.S.A., A.S., S.R., and O.B. acknowledge financial support from the CEFIPRA-ICPAR. K.K.P. and P.S.K. are thankful to CSIR, New Delhi, for financial support. A.S., S.R., and O.B. acknowledge support from the CNRS. R.J.W. and K.I. thank the NIH (GM094919) (EUREKA) and the Science Foundation of Ireland (08/IN.1/B2070) for financial support. The SAIF-CDRI and the LG, Amiens are thanked for analytical facilities. The authors wish to thank Profs I. Huc (Bordeaux) and J. Jiménez-Barbero (Madrid) for their critical reading of the manuscript. This is CSIR-CDRI communication No. 8490. Read 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 onFacebookTwitterLinked InRedditWechat Abstract To fold or not to fold? It is shown that attached sugars play a defining role in the conformations adopted by a pair of novel SAA-derived foldamers in water and that these differences are reflected in the contrasting interactions of these glycofoldamers with various biological targets. C green, O red, N blue, H gray; yellow oval=mannose. Citing Literature Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie_201304239_sm_miscellaneous_information.pdf7.2 MB 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. Volume52, Issue39September 23, 2013Pages 10221-10226 RelatedInformation
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