1YS2

Burkholderia cepacia lipase complexed with hexylphosphonic acid (S) 2-methyl-3-phenylpropyl ester

Summary for 1YS2

• Entry DOI: 10.2210/pdb1ys2/pdb
• Related: 1YS1 3LIP
• Descriptor: Lipase, CALCIUM ION, HEXYLPHOSPHONIC ACID (S)-2-METHYL-3-PHENYLPROPYL ESTER, ... (4 entities in total)
• Functional Keywords: cis peptide bond leu 234, ca2++ ion, inhibitor hexylphosphonic acid (s) 2-methyl-3-phenylpropyl ester, hydrolase
• Biological source: Burkholderia cepacia
• Total number of polymer chains: 1
• Total formula weight: 33399.08

Authors

Mezzetti, A.,Schrag, J.D.,Cheong, C.S.,Kazlauskas, R.J. (deposition date: 2005-02-06, release date: 2005-05-17, Last modification date: 2024-10-30)

Primary citation

Mezzetti, A.,Schrag, J.D.,Cheong, C.S.,Kazlauskas, R.J.
Mirror-Image Packing in Enantiomer Discrimination Molecular Basis for the Enantioselectivity of B.cepacia Lipase toward 2-Methyl-3-Phenyl-1-Propanol.
Chem.Biol., 12:427-437, 2005

PubMed Abstract: Synthetic chemists often exploit the high enantioselectivity of lipases to prepare pure enantiomers of primary alcohols, but the molecular basis for this enantioselectivity is unknown. The crystal structures of two phosphonate transition-state analogs bound to Burkholderia cepacia lipase reveal this molecular basis for a typical primary alcohol: 2-methyl-3-phenyl-1-propanol. The enantiomeric alcohol moieties adopt surprisingly similar orientations, with only subtle differences that make it difficult to predict how to alter enantioselectivity. These structures, along with a survey of previous structures of enzyme bound enantiomers, reveal that binding of enantiomers does not involve an exchange of two substituent positions as most researchers assumed. Instead, the enantiomers adopt mirror-image packing, where three of the four substituents at the stereocenter lie in similar positions. The fourth substituent, hydrogen, points in opposite directions.

PubMed: 15850979
DOI: 10.1016/j.chembiol.2005.01.016

Experimental method

X-RAY DIFFRACTION (1.5 Å)