Synthesis of Functionalized Glutamine‐ and Asparagine‐Type Peptoids – Scope and Limitations |
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Authors: | Carmen Cardenal Sidonie B L Vollrath Ute Schepers Stefan Bräse |
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Institution: | 1. Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz‐Haber‐Weg 6, DE‐76131 Karlsruhe (phone: +49?721?608?4?2902;2. mobile: +49?152?0160?1020;3. fax: +49?721?608?4?8581);4. Institute of Toxicology and Genetics, KIT, Hermann von Helmholtz Platz 1, DE‐76344 Eggenstein‐Leopoldshafen |
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Abstract: | N‐Alkylated glycine oligomers (‘peptoids’) can serve as potent peptidomimetic systems. Installing different functional groups can often be a challenge, and minimizes yields and purities. Here, we describe the synthesis of different amide‐containing submonomers which were obtained as free bases, as well as their incorporation into peptoids. By using the free amines, the coupling results on solid support could be improved, and various functionalized peptoids were prepared. Additionally, an interesting dimerization side reaction leading to cross‐linked peptoids was observed during synthesis. |
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Keywords: | Glutamine Peptoids Peptidomimetic systems Asparagin |
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