50773-56-3Relevant articles and documents
Dendrimer disassembly by benzyl ether depolymerization
Li, Sheng,Szalai, Michael L.,Kevwitch, Robert M.,McGrath, Dominic V.
, p. 10516 - 10517 (2003)
The disassembly of dendritic structures was realized by a cascade cleavage reaction triggered by an initially stimulated group in the dendrimer periphery. A depolymerizable backbone was engineered into prototypical dendritic structures. Evidence for the completion of the disassembly process is provided by the absorbance peak of the p-nitrophenoxide ion that was intentionally installed at the focal point of the dendrons. Observation of the UV spectra during the disassembly process supports a stepwise cascade cleavage proceeding from the periphery into the core. Copyright
Total synthesis of leontopodioside A
Yan, Shiqiang,Zhu, Yueyue,Wang, Yujie,Xiao, Qiang,Ding, Ning,Li, Yingxia
supporting information, (2020/04/08)
Leontopodioside A, isolated from the whole plants of Leontopodium leontopodioides, possesses significant α-glucosidase inhibitory activity. In this work, we studied the total synthesis of leontopodioside A by two strategies for the first time. The optimized strategy involved nine linear steps and has an overall yield of 16.1%. The key feature of the strategy is that glycosylation of chalcone acceptor first followed by the cyclization to construct the flavone scaffold, which has general applicability for the synthesis of flavonoid glycosides.
Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde
Schneider, Tobias,Kubyshkin, Vladimir,Budisa, Nediljko
, p. 2053 - 2063 (2018/05/31)
Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.
