| Title: |
Conception and Synthesis of Sequence‐Coded Morpholinos |
| Authors: |
Pousse, Benoit; Al Ouahabi, Abdelaziz; Baxter, Paul; Charles, Laurence; Lutz, Jean‐françois |
| Contributors: |
Institut de Science et d'ingénierie supramoléculaires (ISIS); Université de Strasbourg (UNISTRA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE); Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique; Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS); Institut Charles Sadron (ICS); Université de Strasbourg (UNISTRA)-Institut National des Sciences Appliquées - Strasbourg (INSA Strasbourg); Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE); Institut de Chimie Radicalaire (ICR); Aix Marseille Université (AMU)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS); ANR-22-PEXM-0004,New polymers as an alternative,Stockage de données massives sur ADN et polymères artificiels(2022) |
| Source: |
ISSN: 0947-6539. |
| Publisher Information: |
CCSD; Wiley-VCH Verlag |
| Publication Year: |
2025 |
| Collection: |
Aix-Marseille Université: HAL |
| Subject Terms: |
[CHIM.POLY]Chemical Sciences/Polymers; [CHIM.THER]Chemical Sciences/Medicinal Chemistry |
| Description: |
International audience ; Solid‐phase morpholino chemistry was explored as a new route to synthesize abiological sequence‐defined oligomers. Two comonomers, 0 and 1 containing (i) a chlorophosphoramidate reactive function, (ii) a trityl‐protected morpholine, and (iii) a coding substituent (H or CH 3 for 0 and 1, respectively) on the morpholine ring were first synthesized and characterized. This binary alphabet was afterwards tested for the synthesis of digitally‐encoded oligomers with different lengths and sequences. The oligomers were prepared on a modified polystyrene resin, cleaved, and characterized by liquid chromatography mass spectrometry. When using a repetitive cycle containing only morpholino coupling and trityl deprotection steps, the formed oligomers were not uniform. Thus, an additional capping step was added. In these conditions, uniform coded sequences were prepared in most cases. Furthermore, the oligomers were analyzed by tandem mass spectrometry. In the studied collision‐induced dissociation conditions, the repeat units of the oligomers undergo two main‐chain fragmentations and full sequence coverage was observed for all studied sequences. Therefore, the binary messages stored in the oligomers could be decoded and retrieved in all cases. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| DOI: |
10.1002/chem.202501161 |
| Availability: |
https://hal.science/hal-05406167; https://hal.science/hal-05406167v1/document; https://hal.science/hal-05406167v1/file/2025%20-%20Lutz%20-%20sequence-coded%20morpholinos%20-%20Chem%20Eur%20J.pdf; https://doi.org/10.1002/chem.202501161 |
| Rights: |
https://creativecommons.org/licenses/by/4.0/ ; info:eu-repo/semantics/OpenAccess |
| Accession Number: |
edsbas.436EB57C |
| Database: |
BASE |