105891-54-1Relevant articles and documents
Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction
Béquignat, Jean-Baptiste,Boucheix, Claude,Canitrot, Damien,Chezal, Jean-Michel,Degoul, Fran?oise,Miot-Noirault, Elisabeth,Moreau, Emmanuel,Navarro-Teulon, Isabelle,Quintana, Mercedes,Rondon, Aurélie,Taiariol, Ludivine,Ty, Nancy
, (2020)
The antibody pretargeting approach for radioimmunotherapy (RIT) using inverse electron demand Diels-Alder cycloaddition (IEDDA) constitutes an emerging theranostic approach for solid cancers. However, IEDDA pretargeting has not reached clinical trial. The major limitation of the IEDDA strategy depends largely on trans-cyclooctene (TCO) stability. Indeed, TCO may isomerize into the more stable but unreactive cis-cyclooctene (CCO), leading to a drastic decrease of IEDDA efficiency. We have thus developed both efficient and reproducible synthetic pathways and analytical follow up for (PEGylated) TCO derivatives, providing high TCO isomeric purity for antibody modification. We have set up an original process to limit the isomerization of TCO to CCO before the mAbs’ functionalization to allow high TCO/tetrazine cycloaddition.
One-pot synthesis of monodisperse dual-functionalized polyethylene glycols through macrocyclic sulfates
Lv, Xiaoyan,Yang, Zhigang,Jiang, Zhong-Xing,Zheng, Xing
, p. 8537 - 8545 (2018/12/01)
Dual-functionalization of monodisperse oligoethylene glycols, especially hetero-functionalization, provides a series of highly valuable intermediates for life and materials sciences. However, the existing methods for the preparation of these compounds suffer excessive protecting and activating group manipulation as well as tedious purification. Here, a one-pot dual-substitution strategy with macrocyclic sulfates of polyethylene glycols as the key intermediates was developed for the convenient and scalable preparation of a series of homo-functionalized and hetero-functionalized oligoethylene glycols in just 1 step. A high synthetic efficacy was achieved by avoiding the protecting and activating group manipulation and the intermediate purification.
A NOVEL, UNEQUIVOCAL SYNTHESIS OF POLYETHYLENE GLYCOLS
Coudert, Gerard,Mpassi, Michel,Guillaumet, Gerald,Selve, Claude
, p. 19 - 26 (2007/10/02)
Unequivocal synthesis of polyethyleneglycols is presented.The key step for this synthesis is the selective monobenzylation of oligoethyleneglycols by the phase transfer catalysis technique.
