Divergent evolution of ligand binding in the o-succinylbenzoate synthase family.

Thermobifida fusca o-succinylbenzoate synthase (OSBS), a member of the enolase superfamily that catalyzes a step in menaquinone biosynthesis, has an amino acid sequence that is 22 and 28% identical with those of two previously characterized OSBS enzymes from Escherichia coli and Amycolatopsis sp. T-1-60, respectively. These values are considerably lower than typical levels of sequence identity among homologous proteins that have the same function. To determine how such divergent enzymes catalyze the same reaction, we determined the structure of T. fusca OSBS and identified amino acids that are important for ligand binding. We discovered significant differences in structure and conformational flexibility between T. fusca OSBS and other members of the enolase superfamily. In particular, the 20s loop, a flexible loop in the active site that permits ligand binding and release in most enolase superfamily proteins, has a four-amino acid deletion and is well-ordered in T. fusca OSBS. Instead, the flexibility of a different region allows the substrate to enter from the other side of the active site. T. fusca OSBS was more tolerant of mutations at residues that were critical for activity in E. coli OSBS. Also, replacing active site amino acids found in one protein with the amino acids that occur at the same place in the other protein reduces the catalytic efficiency. Thus, the extraordinary divergence between these proteins does not appear to reflect a higher tolerance of mutations. Instead, large deletions outside the active site were accompanied by alteration of active site size and electrostatic interactions, resulting in small but significant differences in ligand binding.

[1]  The Structure of a Substrate-Liganded Complex of the L-Ala-D/L-Glu Epimerase from Bacillus subtilis , 2004 .

[2]  Shoshana D. Brown,et al.  Homology models guide discovery of diverse enzyme specificities among dipeptide epimerases in the enolase superfamily , 2012, Proceedings of the National Academy of Sciences.

[3]  A. Vagin,et al.  MOLREP: an Automated Program for Molecular Replacement , 1997 .

[4]  Collaborative Computational,et al.  The CCP4 suite: programs for protein crystallography. , 1994, Acta crystallographica. Section D, Biological crystallography.

[5]  Stephen K Burley,et al.  High throughput protein production and crystallization at NYSGXRC. , 2008, Methods in molecular biology.

[6]  K. Kuwajima,et al.  Folding of staphylococcal nuclease A studied by equilibrium and kinetic circular dichroism spectra. , 1991, Biochemistry.

[7]  S. Bearne,et al.  Structure of mandelate racemase with bound intermediate analogues benzohydroxamate and cupferron. , 2012, Biochemistry.

[8]  J. Gerlt,et al.  Evolution of enzymatic activities in the enolase superfamily: N-succinylamino acid racemase and a new pathway for the irreversible conversion of D- to L-amino acids. , 2006, Biochemistry.

[9]  Matthew P Jacobson,et al.  Computation-facilitated assignment of the function in the enolase superfamily: a regiochemically distinct galactarate dehydratase from Oceanobacillus iheyensis . , 2009, Biochemistry.

[10]  R J Read,et al.  Crystallography & NMR system: A new software suite for macromolecular structure determination. , 1998, Acta crystallographica. Section D, Biological crystallography.

[11]  Heidi J Imker,et al.  Discovery of a dipeptide epimerase enzymatic function guided by homology modeling and virtual screening. , 2008, Structure.

[12]  G. H. Reed,et al.  Chelation of serine 39 to Mg2+ latches a gate at the active site of enolase: structure of the bis(Mg2+) complex of yeast enolase and the intermediate analog phosphonoacetohydroxamate at 2.1-A resolution. , 1994, Biochemistry.

[13]  J. Abrahams,et al.  Methods used in the structure determination of bovine mitochondrial F1 ATPase. , 1996, Acta crystallographica. Section D, Biological crystallography.

[14]  I. Rayment,et al.  Evolution of enzymatic activity in the enolase superfamily: structure of o-succinylbenzoate synthase from Escherichia coli in complex with Mg2+ and o-succinylbenzoate. , 2000, Biochemistry.

[15]  Patricia C Babbitt,et al.  Evolution of enzymatic activities in the enolase superfamily: stereochemically distinct mechanisms in two families of cis,cis-muconate lactonizing enzymes. , 2009, Biochemistry.

[16]  I. Rayment,et al.  Evolution of enzymatic activity in the enolase superfamily: structural studies of the promiscuous o-succinylbenzoate synthase from Amycolatopsis. , 2004, Biochemistry.

[17]  G Bricogne,et al.  Generation, representation and flow of phase information in structure determination: recent developments in and around SHARP 2.0. , 2003, Acta crystallographica. Section D, Biological crystallography.

[18]  Boguslaw Stec,et al.  Crystal structure of enolase indicates that enolase and pyruvate kinase evolved from a common ancestor , 1988, Nature.

[19]  Conrad C. Huang,et al.  UCSF Chimera—A visualization system for exploratory research and analysis , 2004, J. Comput. Chem..

[20]  J. Skolnick,et al.  How well is enzyme function conserved as a function of pairwise sequence identity? , 2003, Journal of molecular biology.

[21]  P. Babbitt,et al.  Evolution of enzymatic activities in the enolase superfamily: D-Mannonate dehydratase from Novosphingobium aromaticivorans. , 2007, Biochemistry.

[22]  I. Rayment,et al.  Evolution of enzymatic activities in the enolase superfamily: crystallographic and mutagenesis studies of the reaction catalyzed by D-glucarate dehydratase from Escherichia coli. , 2000, Biochemistry.

[23]  G L Kenyon,et al.  The role of lysine 166 in the mechanism of mandelate racemase from Pseudomonas putida: mechanistic and crystallographic evidence for stereospecific alkylation by (R)-alpha-phenylglycidate. , 1994, Biochemistry.

[24]  Kevin Cowtan,et al.  research papers Acta Crystallographica Section D Biological , 2005 .

[25]  E. Ortlund,et al.  An epistatic ratchet constrains the direction of glucocorticoid receptor evolution , 2009, Nature.

[26]  R. Gcgaccgagttgctcttgcccc,et al.  Two-Stage PCR Protocol Allowing Introduction of Multiple Mutations , Deletions and Insertions Using QuikChange Site-Directed Mutagenesis , 1999 .

[27]  I. Rayment,et al.  Evolution of enzymatic activity in the enolase superfamily: structural and mutagenic studies of the mechanism of the reaction catalyzed by o-succinylbenzoate synthase from Escherichia coli. , 2003, Biochemistry.

[28]  Ivan Rayment,et al.  Divergent evolution in the enolase superfamily: the interplay of mechanism and specificity. , 2005, Archives of biochemistry and biophysics.

[29]  V. N. Molchanov,et al.  Superconducting Single Crystals of Tl2Ba2CaCu2O8 and YBa2Cu4O8: Crystal Structures in the Vicinity of Tc , 1998 .

[30]  Steven C Almo,et al.  Evolution of enzymatic activities in the enolase superfamily: L-fuconate dehydratase from Xanthomonas campestris. , 2006, Biochemistry.

[31]  G. Petsko,et al.  Mechanism of the reaction catalyzed by mandelate racemase. 2. Crystal structure of mandelate racemase at 2.5-A resolution: identification of the active site and possible catalytic residues. , 1991, Biochemistry.

[32]  Marc A Suchard,et al.  Stability-mediated epistasis constrains the evolution of an influenza protein , 2013, eLife.

[33]  R. Meganathan Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. , 2001, Vitamins and hormones.

[34]  Patricia C Babbitt,et al.  Evolution of enzymatic activities in the enolase superfamily: L-rhamnonate dehydratase. , 2008, Biochemistry.

[35]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[36]  P C Babbitt,et al.  Unexpected divergence of enzyme function and sequence: "N-acylamino acid racemase" is o-succinylbenzoate synthase. , 1999, Biochemistry.

[37]  Heidi J. Imker,et al.  Prediction and assignment of function for a divergent N-succinyl amino acid racemase. , 2007, Nature chemical biology.

[38]  Jie Liang,et al.  CASTp: computed atlas of surface topography of proteins with structural and topographical mapping of functionally annotated residues , 2006, Nucleic Acids Res..

[39]  J. Gerlt,et al.  Evolution of enzymatic activities in the enolase superfamily: D-tartrate dehydratase from Bradyrhizobium japonicum. , 2006, Biochemistry.

[40]  W. Wang,et al.  Two-stage PCR protocol allowing introduction of multiple mutations, deletions and insertions using QuikChange Site-Directed Mutagenesis. , 1999, BioTechniques.

[41]  D. R. Palmer,et al.  The lesser "burden borne" by o-succinylbenzoate synthase: an "easy" reaction involving a carboxylate carbon acid. , 2001, Journal of the American Chemical Society.

[42]  Ivan Rayment,et al.  Evolution of enzymatic activity in the enolase superfamily: functional studies of the promiscuous o-succinylbenzoate synthase from Amycolatopsis. , 2004, Biochemistry.

[43]  Ranyee A. Chiang,et al.  Evolution of structure and function in the o-succinylbenzoate synthase/N-acylamino acid racemase family of the enolase superfamily. , 2006, Journal of molecular biology.

[44]  B. Rost Enzyme function less conserved than anticipated. , 2002, Journal of molecular biology.

[45]  S. Bearne,et al.  Mutational analysis of the active site flap (20s loop) of mandelate racemase. , 2008, Biochemistry.

[46]  K. Berka,et al.  Binding of quinidine radically increases the stability and decreases the flexibility of the cytochrome P450 2D6 active site. , 2012, Journal of inorganic biochemistry.

[47]  M. E. Glasner,et al.  Residues required for activity in Escherichia coli o-succinylbenzoate synthase (OSBS) are not conserved in all OSBS enzymes. , 2012, Biochemistry.