In:
ChemBioChem, Wiley, Vol. 16, No. 1 ( 2015-01-02), p. 77-82
Kurzfassung:
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.
Materialart:
Online-Ressource
ISSN:
1439-4227
,
1439-7633
DOI:
10.1002/cbic.201402563
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2015
ZDB Id:
2020469-3
SSG:
12
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