Equipe de Chimie Bio-Organique, COBRA-CNRS UMR 6014 & FR 3038, rue Lucien Tesnière, 76131 Mont-Saint-Aignan, France.
Org Biomol Chem. 2010 Feb 7;8(3):676-90. doi: 10.1039/b920193a. Epub 2009 Dec 8.
A series of simplified microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for their binding affinity by the monoclonal antibody mAb MC159, an anti-microcystin-LR mAb recently selected by us for the detection of microcystins through various immunoassay formats. Some modifications have been brought to the enantiospecific synthesis of N-Boc-Adda developed by Pearson et al. (Org. Lett., 2000, 2, 2901) which enabled us to access in an economical and time-saving manner a small library of MC-LR linear analogues. Among which Adda was chosen to synthesise, as an illustrative example, a fluorescent probe derived from this beta-amino acid. This probe was subsequently solid-phase immobilised by means of oxime ligation in order to lead to biochips suitable for microcystin detection through the SPIT-FRI method.
已合成了一系列基于 Adda [(2S,3S,8S,9S,4E,6E)-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基- decadienoic acid]或其相应 aldol 前体与多肽部分连接的简化微囊藻毒素-LR 类似物，并通过我们最近为通过各种免疫分析格式检测微囊藻毒素而选择的抗微囊藻毒素-LR mAb mAb MC159 评估其结合亲和力。对 Pearson 等人开发的 N-Boc-Adda 的对映选择性合成进行了一些修改（Org。Lett.，2000，2，2901），这使我们能够以经济和节省时间的方式获得微囊藻毒素-LR 线性类似物的小型文库。其中 Adda 被选择作为示例来合成源自这种β-氨基酸的荧光探针。该探针随后通过肟连接固相固定化，以便通过 SPIT-FRI 方法制备适合微囊藻毒素检测的生物芯片。
