5672-83-3Relevant articles and documents
An access to aza-Freidinger lactams and E-locked analogs
Ottersbach, Philipp A.,Schmitz, Janina,Schnakenburg, Gregor,Gütschow, Michael
supporting information, p. 448 - 451 (2013/04/11)
Freidinger lactams, possessing a peptide bond configuration locked to Z, are important key elements of conformationally restricted peptidomimetics. In the present work, the CαHi+1 unit has been replaced by N, leading to novel aza-Fre
Synthesis of carbosilane dendritic wedges and their use for the construction of dendritic receptors
Van Heerbeek, Rieko,Kamer, Paul C. J.,Van Leeuwen, Piet N.M.W.,Reek, Joost N.H.
, p. 211 - 223 (2007/10/03)
A divergent route for the synthesis of carbosilane wedges that contain either a bromine or amine as focal point has been developed. These new building blocks enable the construction of various core-functionalized carbosilane dendrimers. As a typical example carbosilane dendrimers up to the third generation containing a N,N′,N″-1,3,5-benzenetricarboxamide core (G1-G3) have been synthesized. This new class of molecules has been studied as host molecules and they have been found to bind protected amino acids as guest molecules via hydrogen bonding interactions. A decrease in the association constants was observed for the higher generation dendritic hosts, which is attributed to the increased steric hindrance around the core where the binding site is located. The binding properties of the dendritic host molecules can be tuned by modifying the binding motif at the core of the carbosilane dendrimers. A higher association constant for N-CBZ-protected glutamic acid 1-methyl ester (5) was observed when the third generation N,N′,N″-1,3,5-tris(l- alaninyl)benzenetricarboxamide core-functionalized carbosilane dendrimer (G3′) was used as the host molecule compared to G3. Different association constants for the formation of the diastereomeric G3′·l-5 (K = 295 M-1) and G3′·d-5 (K = 236 M-1) host-guest complexes were observed, pointing to a small enantioselective recognition effect. The difference between the association constants for the formation of the G3′·(l-5)2 and G3′·(d-5)2 host-guest complexes was much more pronounced, K = 37 M-1 versus K = 10 M-1, respectively. The Royal Society of Chemistry 2006.
Synthesis of (S)-2-amino-8-oxodecanoic acid (Aoda) and apicidin A
Mou, Liyuan,Singh, Gurdial
, p. 6603 - 6606 (2007/10/03)
The synthesis of (S)-2-amino-8-oxodecanoic acid, a constituent of the cyclic tetrapeptides, the apicidins, was accomplished under photolytic conditions in the presence of tri-n-butyltin hydride using glutamic acid. This enabled a total synthesis of apicidin A to be completed.