4D5E

Crystal Structure of recombinant wildtype CDH

Summary for 4D5E

• Entry DOI: 10.2210/pdb4d5e/pdb
• Related: 4D5G
• Descriptor: CYCLOHEXANE-1,2-DIONE HYDROLASE, DI(HYDROXYETHYL)ETHER, NONAETHYLENE GLYCOL, ... (12 entities in total)
• Functional Keywords: hydrolase, c-c bond cleavage, c-c bond formation
• Biological source: AZOARCUS SP. BH72
• Total number of polymer chains: 2
• Total formula weight: 133596.47

Authors

Loschonsky, S.,Wacker, T.,Waltzer, S.,Giovannini, P.P.,McLeish, M.J.,Andrade, S.L.A.,Mueller, M. (deposition date: 2014-11-03, release date: 2015-01-21, Last modification date: 2024-05-08)

Primary citation

Loschonsky, S.,Wacker, T.,Waltzer, S.,Giovannini, P.P.,Mcleish, M.J.,Andrade, S.L.A.,Muller, M.
Extended Reaction Scope of Thiamine Diphosphate Dependent Cyclohexane-1,2-Dione Hydrolase: From C-C Bond Cleavage to C-C Bond Ligation.
Angew.Chem.Int.Ed.Engl., 53:14402-, 2014

PubMed Abstract: ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) catalyzes the CC bond cleavage of cyclohexane-1,2-dione to 6-oxohexanoate, and the asymmetric benzoin condensation between benzaldehyde and pyruvate. One of the two reactivities of CDH was selectively knocked down by mutation experiments. CDH-H28A is much less able to catalyze the CC bond formation, while the ability for CC bond cleavage is still intact. The double variant CDH-H28A/N484A shows the opposite behavior and catalyzes the addition of pyruvate to cyclohexane-1,2-dione, resulting in the formation of a tertiary alcohol. Several acyloins of tertiary alcohols are formed with 54-94 % enantiomeric excess. In addition to pyruvate, methyl pyruvate and butane-2,3-dione are alternative donor substrates for CC bond formation. Thus, the very rare aldehyde-ketone cross-benzoin reaction has been solved by design of an enzyme variant.

PubMed: 25382418
DOI: 10.1002/ANIE.201408287

Experimental method

X-RAY DIFFRACTION (1.43 Å)