Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support.
A combinatorial synthesis of 24-member RGD models was accomplished on polymer-support. Ortho-, meta-, and para-iodobenzylamines loaded on an aldehyde linker by reductive amination were coupled with RGD sequences and various omega-amino acids by a split-and-pool method. Palladium-catalyzed carbonylative macrolactamization of the polymer-supported cyclization precursors, followed by acid cleavage, provided conformationally restricted RGD model cyclic peptides.
Kamioka
Seiji
S
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
Shimazu
Sayaka
S
Doi
Takayuki
T
Takahashi
Takashi
T
D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D007462:Iodobenzenes / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008956:Models, Chemical; D009842:Oligopeptides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry*
D000447:Aldehydes; D000970:Antineoplastic Agents; D007462:Iodobenzenes; D007769:Lactams; D047028:Macrocyclic Compounds; D009842:Oligopeptides; D010456:Peptides, Cyclic; D011108:Polymers; D010165:Palladium; C047981:arginyl-glycyl-aspartic acid