Department of Chemistry and ‡Department of Biochemistry and Molecular Biophysics, Kansas State University , Manhattan, Kansas 66506, United States.
Org Lett. 2017 Apr 7;19(7):1820-1823. doi: 10.1021/acs.orglett.7b00587. Epub 2017 Mar 22.
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.
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。
