Naslov
Synthesis of bis-peptides attached on poly[n]norbornane molecular scaffolds with well-defined relative positions and distances

Autori
Shang, Muhong ; Warrener, Ronald N. ; Butler, Doug N. ; Margetić, Davor ; Murata, Yasujiro

Izvornik
Molecular diversity (1381-1991) 15 (2011), 2; 541-560

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
peptides; cycloaddition reactions; polycycles; peptidomimetics

Sažetak
This paper describes novel synthetic approaches to polynorbornane 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 polynorbornane 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA