An NMR and MD Modeling Insight into Nucleation of 1,2-Alkanediols: Selective Crystallization of Lipase-Catalytically Resolved Enantiomers from the Reaction Mixtures

作者:Parve Omar; Reile Indrek; Parve Jaan; Kasvandik Sergo; Kudrjasova Marina; Tamp Sven; Metsala Andrus; Villo Ly*; Pehk Tonis; Jarvet Jueri; Vares Lauri
来源:Journal of Organic Chemistry, 2013, 78(24): 12795-12801.
DOI:10.1021/jo402189e

摘要

The work on developing a scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediols, complemented by crystallization of the pure enantiomers from the reaction mixtures, offered the possibility of a more detailed study of the aggregation of such diols. MD modeling, mass spectrometry, H-1 NMR, and DOSY studies provided a novel insight into the nucleation process. An efficient protocol for stereo- and chemoselective crystallization of (S)-1,2-dodecanediol and related compounds from the crude bioconversion mixtures was developed.

  • 出版日期2013-12-20