Regioselective chemoenzymatic syntheses of ferulate conjugates as chromogenic substrates for feruloyl esterases
نویسندگان
چکیده
Generally, carbohydrate-active enzymes are studied using chromogenic substrates that provide quick and easy color-based detection of enzyme-mediated hydrolysis. For feruloyl esterases, commercially available ferulate derivatives both costly limited in terms their experimental application. In this study, we describe solutions for these two issues, a chemoenzymatic approach to synthesize different compounds. The overall synthetic routes towards 5-bromo-4-chloro-3-indolyl 4-nitrophenyl 5- O -feruloyl-α-ʟ-arabinofuranosides were significantly shortened (from 7 or 8 4–6 steps), the transesterification yields enhanced 46 73% from 47 86%, respectively). This was achieved enzymatic (immobilized Lipozyme ® TL IM Thermomyces lanuginosus ) unprotected vinyl primary hydroxy group α‐ʟ‐arabinofuranosides. Moreover, novel feruloylated 4-nitrocatechol-1-yl-substituted butanetriol analog, containing cleavable hydroxylated linker, also synthesized 32% yield 3 steps (convergent synthesis). latter route combined regioselective functionalization 4-nitrocatechol transferuloylation. use strategy characterize type A esterase Aspergillus niger reveals advantages substrate characterizations esterases.
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ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2021
ISSN: ['2195-951X', '1860-5397']
DOI: https://doi.org/10.3762/bjoc.17.30