Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support.

Seiji Kamioka, Sayaka Shimazu, Takayuki Doi, Takashi Takahashi
Author Information
  1. Seiji Kamioka: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.

Abstract

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.

MeSH Term

Aldehydes
Amination
Antineoplastic Agents
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Iodobenzenes
Lactams
Macrocyclic Compounds
Models, Chemical
Oligopeptides
Palladium
Peptides, Cyclic
Polymers

Chemicals

Aldehydes
Antineoplastic Agents
Iodobenzenes
Lactams
Macrocyclic Compounds
Oligopeptides
Peptides, Cyclic
Polymers
Palladium
arginyl-glycyl-aspartic acid

Word Cloud

Created with Highcharts 10.0.0RGDsynthesiscarbonylativemacrolactamizationmodelcyclicpeptidescombinatorial24-membermodelsaccomplishedpolymer-supportOrtho-meta-para-iodobenzylaminesloadedaldehydelinkerreductiveaminationcoupledsequencesvariousomega-aminoacidssplit-and-poolmethodPalladium-catalyzedpolymer-supportedcyclizationprecursorsfollowedacidcleavageprovidedconformationallyrestrictedCombinatorialutilizingpalladium-catalyzedpolymersupport

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