Alpha selective epoxide opening with 18F-: synthesis of 4-(3-[18F]fluoro-2-hydroxypropoxy)benzaldehyde ([18F]FPB) for peptide labeling

被引：7

作者：

Schirrmacher, Ralf ^{[1
]}

Lucas, Philippe ^{[1
]}

Schirrmacher, Esther ^{[1
]}

Waengler, Bjoern ^{[2
]}

Waengler, Carmen ^{[1
,2
]}

机构：

[1] McGill Univ, Jewish Gen Hosp, Lady Davis Inst Med Res, Montreal, PQ H3T 1E2, Canada

[2] Univ Munich, Dept Nucl Med, D-81377 Munich, Germany

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 16期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Epoxide opening; F-18-labeling; F-18]MISO; Peptide labeling; tert-Amyl-alcohol; POTENTIAL TOOLS; FLUORINATION; RGD;

D O I：

10.1016/j.tetlet.2011.02.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strained tricyclic ring systems such as epoxides are rarely used as precursors for the introduction of anionic fluorine-18 into organic compounds intended for positron emission tomography (PET). Here we report the alpha selective ring opening of epoxides for the introduction of fluorine-18 into small as well as larger biomolecules via 1- and 2-step protocols. [F-18]fluoromisonidazole ([(18)]MISO), a tracer for hypoxia imaging, and the tumor targeting peptide Tyr(3)-octreotate (TATE) were radiolabeled using epoxide opening reactions. In the latter case, the new prosthetic labeling synthon 4-(3-[F-18]fluoro-2-hydroxypropoxy)benzaldehyde([F-18]FPB) has been used for F-18-introduction. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1973 / 1976

页数：4

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