Solid-phase organic tagging resins for labeling biomolecules by 1,3-dipolar cycloaddition: Application to the synthesis of a fluorescent non-peptidic vasopressin receptor ligand

Bonnet D; Riche S; Loison S; Dagher R; Frantz MC; Boudier L; Rahmeh R; Mouillac B; Haiech J; Hibert M

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Solid-phase organic tagging resins for labeling biomolecules by 1,3-dipolar cycloaddition: Application to the synthesis of a fluorescent non-peptidic vasopressin receptor ligand

机译：通过1,3-偶极环加成标记生物分子的固相有机标记树脂：在合成荧光非肽加压素受体配体中的应用

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Two novel solid-phase organic tagging (SPOrT) resins were synthesized to facilitate the labeling of peptides and small organic compounds with a fluorescent probe. Both resins were obtained from the commercially available backbone amide linker (BAL) resin. Following the solid-phase synthesis of model compounds, a tripeptide and benzazepine, the fluorescent probe derived from Lissamine Rhodamine B was incorporated through Cu-I-catalyzed 1,3-dipolar cycloaddition. Final cleavage in acidic media enabled access to both types of molecules in good yield with high purity. The SPOrT resin was successfully applied to the preparation of the first non-peptidic fluorescent compound with a nanomolar affinity for the human vasopressin V-2 receptor (V2R) subtype. This molecule will find application in binding assays that use polarization or fluorescence resonance energy-transfer (FRET) techniques. The SPOrT resins are also well suited for other tags and the parallel synthesis of a fluorescently tagged library for protein screening.

机译：合成了两种新型的固相有机标记（SPOrT）树脂，以利于使用荧光探针标记肽和小的有机化合物。两种树脂均购自市售的骨架酰胺连接基（BAL）树脂。在模型化合物，三肽和苯并ze庚因的固相合成之后，通过铜-I催化的1,3-偶极环加成反应，引入了衍生自Lissamine Rhodamine B的荧光探针。在酸性介质中的最终裂解使得能够以高收率和高纯度接近两种类型的分子。 SPOrT树脂已成功应用于制备第一个对人血管加压素V-2受体（V2R）亚型具有纳摩尔摩尔亲和力的非肽荧光化合物。该分子将在使用极化或荧光共振能量转移（FRET）技术的结合测定中找到应用。 SPOrT树脂也非常适用于其他标签和用于蛋白质筛选的荧光标签文库的并行合成。

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《Chemistry: A European journal》 |2008年第20期|共8页
作者
Bonnet D; Riche S; Loison S; Dagher R; Frantz MC; Boudier L; Rahmeh R; Mouillac B; Haiech J; Hibert M;
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正文语种 eng
中图分类化学;
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click chemistry; cycloaddition; fluorescent probes; receptors; solid-phase synthesis; COPPER(I)-CATALYZED AZIDE-ALKYNE; CLICK-CHEMISTRY; CORRELATION SPECTROSCOPY; BIOLOGICAL EVALUATION; TERMINAL ALKYNES; BINDING; LINKER; PEPTIDOTRIAZOLES; BIOCONJUGATION; POLARIZATION;

机译：点击化学;环加成;荧光探针;受体;固相合成;铜（I）催化的叠氮化物-烯烃;点击化学;相关光谱;生物学评价;末端烷基;键合;连接剂;肽三唑;生物固结;

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1. Solid-phase organic tagging resins for labeling biomolecules by 1,3-dipolar cycloaddition: Application to the synthesis of a fluorescent non-peptidic vasopressin receptor ligand [J] . Bonnet D, Riche S, Loison S, Chemistry: A European journal . 2008,第20期

机译：通过1,3-偶极环加成标记生物分子的固相有机标记树脂：在合成荧光非肽加压素受体配体中的应用
2. The solid-phase parallel synthesis of beta-strand mimetic templates via 1,3-dipolar cycloaddition with resin-bound vinylsulfone [J] . Fuchi N., Doi T., Cao B., Synlett . 2002,第2期

机译：通过1,3-偶极环加成与树脂结合的乙烯基砜固相平行合成β-链模拟模板
3. Solid-Phase Synthesis of Cleavable N-Arylmaleimides: Applications in 1,3-Dipolar Cycloaddition and in Thiol Scavenging [J] . Hamid R. Hoveyda, Dennis G. Hall Organic letters . 2001,第22期

机译：可裂解N-芳基马来酰亚胺的固相合成：在1，3-偶极环加成反应和硫醇清除中的应用
4. Peptidotriazoles:copper(I)-catalyzed 1,3-dipolar cycloadditions on solid-phase [C] . Christian W.Tornoe, Morten Meldal the International Peptide Symposium . 2001

机译：肽二唑：铜（I） - 催化在固相上的1,3-偶极环加成
5. The synthesis of isoxazol(in)es via 1,3-dipolar cycloaddition, other heterocyclic systems, and developments in solid-phase organic synthesis. [D] . Sammelson, Robert Erik. 2001

机译：通过1,3-偶极环加成反应，其他杂环体系和固相有机合成的进展来合成异恶唑（in）es。
6. Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer [O] . Sagnik Sengupta, Mena Asha Krishnan, Premansh Dudhe, 2018

机译：新颖的固相策略合成配体靶向的荧光标记的螯合肽共轭物作为治疗癌症的工具
7. Synthesis of Chirl N,P-ligands Derived fromL-Proline and Its Application to 1,3-Dipolar Cycloaddition [O] . Hong Chen, Qian Chen 2013

机译：合成剑道，p-配体衍生自脯氨酸及其在1,3-偶极环加成的应用

Solid-phase organic tagging resins for labeling biomolecules by 1,3-dipolar cycloaddition: Application to the synthesis of a fluorescent non-peptidic vasopressin receptor ligand

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