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Synthesis and preliminary biological evaluation of new phenolic and catecholic dehydroamino acid derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2017-09-14 , DOI: 10.1016/j.tet.2017.09.012
Luís S. Monteiro , Sandra Oliveira , Fátima Paiva-Martins , Paula M.T. Ferreira , David M. Pereira , Paula B. Andrade , Patrícia Valentão

A library of N-phenolic and N-catecholic dehydroamino acid derivatives was prepared using an innovative synthetic strategy that involves mild reaction conditions and simple work-up procedures. The method comprises coupling of phenolic or catecholic acids with β-hydroxyamino acids followed by tert-butyloxycarbonylation of all hydroxyl groups using tert-butyldicarbonate and 4-dimethylaminopyridine as catalyst. Treatment of these amino acids with N,N,N′,N′-tetramethylguanidine affords the corresponding O-tert-butyloxycarbonyldehydroamino acid derivative. Deprotection of the aromatic hydroxyl groups is carried out with trifluoroacetic acid. This synthetic strategy can be applied in a one-pot procedure and yields compounds that can be easily inserted into peptides or other biomolecules after cleavage of the C-protecting group. Preliminary studies of cell viability show that these new compounds display very low or no toxicity. These dehydroamino acids with a phenolic or catecholic moiety can have intrinsic biological activity or used to prepare new hydrogels that mimic mussel adhesive proteins.



中文翻译:

新型酚和儿茶酚脱氢氨基酸衍生物的合成及初步生物学评价

使用创新的合成策略(包括温和的反应条件和简单的后处理步骤),制备了N-酚和N-邻苯二酚脱氢氨基酸衍生物的文库。该方法包括将酚酸或儿茶酸与β-羟基氨基酸偶联,然后使用碳酸二叔丁酯和4-二甲基氨基吡啶作为催化剂,将所有羟基的丁氧基基化。这些氨基酸与处理N,N,N',N' -四甲基胍,得到相应的ø --丁氧羰基脱氢氨基酸衍生物。芳族羟基的脱保护用三氟乙酸进行。这种合成策略可应用于一锅法,并产生可在C保护基裂解后轻松插入肽或其他生物分子中的化合物。对细胞活力的初步研究表明,这些新化合物显示出极低的毒性或无毒性。这些具有酚或儿茶酚部分的脱氢氨基酸可以具有固有的生物学活性,或用于制备模拟贻贝粘附蛋白的新水凝胶。

更新日期:2017-09-14
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