对映选择性合成二木脂素模型化合物及其与染料褪色过氧化物酶的立体选择性研究。
Enantioselective Synthesis of Dilignol Model Compounds and Their Stereodiscrimination Study with a Dye-Decolorizing Peroxidase.
机构信息
Department of Chemistry and ‡Department of Biochemistry and Molecular Biophysics, Kansas State University , Manhattan, Kansas 66506, United States.
出版信息
Org Lett. 2017 Apr 7;19(7):1820-1823. doi: 10.1021/acs.orglett.7b00587. Epub 2017 Mar 22.
Abstract
A four-step enantioselective approach was developed to synthesize anti (1R,2S)-1a and (1S,2R)-1b containing a β-O-4 linkage in good yields. A significant difference was observed for the apparent binding affinities of four stereospecific lignin model compounds with TcDyP by surface plasmon resonance, which was not translated into a significant difference in enzyme activities. The discrepancy may be attributed to the conformational change involving a loop widely present in DyPs upon HO binding.
摘要
发展了一种四步对映选择性方法来合成含有β-O-4 键的反式（1R,2S）-1a 和（1S,2R）-1b，产率良好。通过表面等离子体共振观察到四种立体特异性木质素模型化合物与 TcDyP 的表观结合亲和力存在显著差异，但这并没有转化为酶活性的显著差异。这种差异可能归因于 HO 结合时 DyP 中广泛存在的环构象变化。
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