Convergent synthesis of degradable dendrons based on l-malic acid

Autor:	Ulrich Meyhoff, Ulla Riber, Ulrik Boas
Rok vydání:	2015
Předmět:	Fumaric acid Convergent synthesis Regioselectivity General Chemistry High-performance liquid chromatography Catalysis Polyester chemistry.chemical_compound chemistry Dendrimer Materials Chemistry Organic chemistry Degradation (geology) Malic acid
Zdroj:	New Journal of Chemistry. 39:1161-1171
ISSN:	1369-9261 1144-0546
DOI:	10.1039/c4nj01156b
Popis:	New degradable polyester dendrons based on the cellular tricarboxylic acid cycle component L-malic acid were synthesized up to the third generation by convergent synthesis. The dendron wedges could be introduced in a stepwise, highly regioselective fashion. HMBC-NMR revealed that the C1-carbonyl on malic acid was exclusively esterified, before the reaction of the second dendron wedge at C4 took place. Degradation studies on a first generation dendron analyzed by HPLC showed that hydrolytic degradation of the dendron most profoundly takes place at pH 4 and pH 9 with the highest degradation rate at alkaline pH. NMR shows that the dendron degrades to malic acid and fumaric acid derivatives. Preliminary studies performed in the cell culture show low toxicity of the dendrons in concentrations of up to 50 μg mL−1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4a4fee175e5b9de5b28e0ca596759aba https://doi.org/10.1039/c4nj01156b Zobrazit plný text záznamu