Synthesis of cyclic RGD derivatives via solid phase macrocyclization using the Heck reaction

被引:33
作者
Akaji, K
Teruya, K
Akaji, M
Aimoto, S
机构
[1] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan
[2] Kyoto Univ, Fac Pharmaceut Sci, Sakyo Ku, Kyoto 6068304, Japan
关键词
RGD derivatives; Heck reaction; cyclic tetrapeptide; solid phase macrocyclization; tert-alcohol resin;
D O I
10.1016/S0040-4020(01)00113-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel intramolecular macrocyclization reaction on a solid support using the Heck reaction has been achieved. For head to tail cyclization on a solid support, the linear precursor was anchored to a chlorotrityl chloride resin via an ester linkage using the P-carboxyl group of Asp. The Heck coupling of acrylic acid amide to 3-iodobenzylamine on the solid support proceeds smoothly to yield a cyclic tetrapeptide derivative, which contains a new 3-substituted cinnamic acid template and Arg-Gly-Asp sequence. The macrocyclization reaction takes place considerably more rapidly on a solid support than in solution. The solid phase procedure was successfully used for the construction of cyclic RGD libraries having diverse side chain structures, combined with a variety of ring sizes. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2293 / 2303
页数:11
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