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  • Title: Hydrogen-bonding-driven enantioselective resolution against the Kazlauskas rule to afford γ-amino alcohols by Candida rugosa lipase.
    Author: Min B, Park J, Sim YK, Jung S, Kim SH, Song JK, Kim BT, Park SY, Yun J, Park S, Lee H.
    Journal: Chembiochem; 2015 Jan 02; 16(1):77-82. PubMed ID: 25477295.
    Abstract:
    Most lipases resolve secondary alcohols in accordance with the "Kazlauskas rule" to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan-2-ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4-(tert-butoxycarbonylamino)butan-2-ol, which has a similar chain length to heptan-2-ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.
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