caa a22 4500 445878959 CHVBK 20180317145536.0 cr unu---uuuuu 170323e20110501xx s 000 0 eng 10.1007/s11030-010-9279-9 doi (NATIONALLICENCE)springer-10.1007/s11030-010-9279-9 Synthesis of bis-peptides attached on poly[ n ]norbornene molecular scaffolds with well-defined relative positions and distances [Elektronische Daten] [Muhong Shang, Ronald Warrener, Douglas Butler, Yasujiro Murata, Davor Margetić] This article describes novel synthetic approaches to polynorbornene molecular scaffolds substituted with peptides at various, well-defined positions. A library of norbornene building blocks with attached peptides was prepared. Alkene cyclobutane epoxide (ACE) coupling method was used as a key step reaction for the connection of two norbornene building blocks into bis-peptide scaffolds. Photodimerization of cyclobutene diesters offers an alternative route to polynorbornene bis-peptides. Pyrrolo-peptides were used for preparation of peptide-substituted 7-aza norbornenes. Asymmetrical bis-peptide scaffolds were prepared by ACE coupling of peptide-norbornane epoxide with another norbornene-peptide block. Chemical elaboration of bridgehead dimethyl esters of ACE products or epoxide ACE reagents was also used for peptide attachment. Springer Science+Business Media B.V., 2010 Peptides nationallicence Cycloaddition reactions nationallicence Polycycles nationallicence Peptidomimetics nationallicence Norbornene nationallicence Shang Muhong Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut Warrener Ronald Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut Butler Douglas Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut Murata Yasujiro Institute for Chemical Research, Kyoto University, 611-0011, Uji, Kyoto, Japan aut Margetić Davor Laboratory for Physical Organic Chemistry, Department of Organic Chemistry and Biochemistry, Ruder Bošković Institute, Bijenička c. 54, 10000, Zagreb, Croatia aut Molecular Diversity Springer Netherlands 15/2(2011-05-01), 541-560 1381-1991 15:2<541 2011 15 11030 https://doi.org/10.1007/s11030-010-9279-9 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-010-9279-9 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Shang Muhong Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut NATIONALLICENCE 700 1- Warrener Ronald Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut NATIONALLICENCE 700 1- Butler Douglas Centre for Molecular Architecture, Central Queensland University, 4702, Rockhampton, QLD, Australia aut NATIONALLICENCE 700 1- Murata Yasujiro Institute for Chemical Research, Kyoto University, 611-0011, Uji, Kyoto, Japan aut NATIONALLICENCE 700 1- Margetić Davor Laboratory for Physical Organic Chemistry, Department of Organic Chemistry and Biochemistry, Ruder Bošković Institute, Bijenička c. 54, 10000, Zagreb, Croatia aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/2(2011-05-01), 541-560 1381-1991 15:2<541 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer