1616668-55-3Relevant academic research and scientific papers
Building blocks for the construction of bioorthogonally reactive peptides via solid-phase peptide synthesis
Zeglis, Brian M.,Emmetiere, Fabien,Pillarsetty, Nagavarakishore,Weissleder, Ralph,Lewis, Jason S.,Reiner, Thomas
, p. 48 - 53 (2014)
The need for post-synthetic modifications and reactive prosthetic groups has long been a limiting factor in the synthesis and study of peptidic and peptidomimetic imaging agents. In this regard, the application of biologically and chemically orthogonal reactions to the design and development of novel radiotracers has the potential to have far-reaching implications in both the laboratory and the clinic. Herein, we report the synthesis and development of a series of modular and versatile building blocks for inverse electron-demand Diels-Alder copper-free click chemistry: tetrazine-functionalized artificial amino acids. Following the development of a novel peptide coupling protocol for peptide synthesis in the presence of tetrazines, we successfully demonstrated its effectiveness and applicability. This versatile methodology has the potential to have a transformational impact, opening the door for the rapid, facile, and modular synthesis of bioorthogonally reactive peptide probes. The earlier, the better! We report a novel synthesis of tetrazine-functionalized artificial amino acids, the creation of a model tetrazine-containing pentapeptide using solid-phase peptide synthesis, and the facile and rapid bioorthogonal radiolabeling of this peptide using a 89Zr- desferrioxamine-labeled trans-cyclooctene.
TETRAZINES/TRANS-CYCLOOCTENES IN SOLID PHASE SYNTHESIS OF LABELED PEPTIDES
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Paragraph 0148, (2016/01/01)
This invention is in the field of labeled peptide construction for medical treatment and analysis. The invention relates to synthetic labeled peptide compositions, methods of synthesis, and methods of use for the synthetic labeled peptide compositions for medical treatment, imaging, and research purposes.
