Synthesis of bis-peptides attached on poly[n]norbornene molecular scaffolds with well-defined relative positions and distances |
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Authors: | Muhong Shang Ronald N Warrener Douglas N Butler Yasujiro Murata and Davor Margeti? |
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Institution: | (1) The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, Taipei, 11529, Taiwan, ROC; |
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Abstract: | 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. |
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Keywords: | |
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