Table S1. Computational details for the reaction of {[(NH 3 ) 2 Cu]-(O 2 )-[Cu(NH 3 ) 2 ]} 2+ with 4-carboxamidophenolate.
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1 SI 1 Supporting Information: Structure/function correlations among coupled binuclear copper proteins through spectroscopic and reactivity studies of NspF Supplementary Materials and Methods. Protein Expression and Purification. E. coli BL21(DE3) harboring the His 6 -tagged NspF expression plasmid (1) was precultured at 37 C for 16 h in Luria-Bertani broth containing 50 µg/ml ampicillin. The preculture (2 ml) was inoculated into 2 L of the same medium and cultivated at 37 C until the D 600 reached 0.5. Then isopropyl-β-d-thiogalactoside was added to the broth, which had been cooled to 15 C, to a final concentration of 0.2 mm, followed by further cultivation at 15 C for 48 h. The E. coli cells were harvested by centrifugation and disrupted by ultrasonication as described previously (1). The crude extract was obtained by removing cell debris by centrifugation (10,000 g, 15 min). CuS 4 was added to the crude extract to a final concentration of 1 mm, followed by centrifugation of the mixture at 30,000 g for 15 min. The crude extract was then purified by chromatography and the His 6 -tag was removed from the recombinant NspF protein by a restriction protease as previously described (1). Fig. S1. xygen consumption with two substrates; 4-methylphenol (A) and 4-carboxamidophenol (B). 1) NspF (200 nm), substrate (1.02 mm), and hydroxylamine (1.01 mm). 2) NspF and substrate. 3) Substrate and hydroxylamine. 4) NspF and hydroxylamine.
2 SI 2 Fig. S2. HPLC product analysis of 60 nm recombinant S. glaucescens tyrosinase (A) with 4-methylphenol (1.02 mm) and hydroxylamine (1.01 mm) (1). Chromatographic traces in the absence of tyrosinase (2), hydroxylamine (3), and 4-methylphenol (4) are shown. Identical chromatographs with 200 nm NspF (B) indicate that both NspF and Ty produce an identical product (RT = 2.21 min) under these reaction conditions. The UV-Vis of this chromatographic peak for tyrosinase (C) and NspF (D) is also identical. Table S1. Computational details for the reaction of {[( ) 2 Cu]-( 2 )-[Cu( ) 2 ]} 2+ with 4-carboxamidophenolate. C C C Cu Cu NH Cu Cu 3 A Ty TS Ty B Ty Functional RB3LYP RB3LYP RB3LYP Basis Set TZVP TZVP TZVP Charge Multiplicity Point Group C 1 C 1 C 1 Solvation THF with PCM THF with PCM THF with PCM Integral Grid ultrafine ultrafine ultrafine SCF Energy (a.u.) Imaginary Frequencies Selected Metrical Parameters Cu Cu (Å) Cu (Å) 1.803, 1.805, 1.825, 1.860, 1.835, , Cu Sub (Å) (Å) C (Å) NH Cu Cu , 1.839, 1.948, 2.961
3 Table S2. Computational details for the reaction of {[( ) 2 Cu]-( 2 )-[Cu( ) 2 ]} 2+ aminocarbonly-phenolate. CNH C C 2 SI 3 with 2-amino-4- Cu Cu A NspF TS NspF B NspF Functional RB3LYP RB3LYP RB3LYP Basis Set TZVP TZVP TZVP Charge Multiplicity Point Group C 1 C 1 C 1 Solvation THF with PCM THF with PCM THF with PCM Integral Grid ultrafine ultrafine ultrafine SCF Energy (a.u.) Imaginary Frequencies Selected Metrical Parameters Cu Cu (Å) Cu (Å) 1.803, 1.808, 1.819, 1.854, 1.842, , Cu Sub (Å) (Å) N (Å) Cu Cu Cu Cu 1.809, 1.834, 1.992, Table S3. Cartesian coordinates of A Ty C C H C C H C H C Cu Cu N H N H N H N H H H H H H H H H H C N H H Table S4. Cartesian coordinates of TS Ty C C H C C H C H C Cu Cu N H N H N H N H H H H H H H H H H C N H H Table S5. Cartesian coordinates of B Ty C C H C C H C H C Cu Cu N H N H N H N H H H H H H H H H H C N H H
4 Table S6. Cartesian coordinates of A NspF C C H C C H C H C Cu Cu N H N H N H N H C N H H N H H H H H H H H H H Table S7. Cartesian coordinates of TS NspF C C H C C H C H C Cu Cu N H N H N H N H C N H H N H H H H H H H H H H SI 4 Table S8. Cartesian coordinates of B NspF C C H C C H C H C Cu Cu N H N H N H N H C N H H N H H H H H H H H H H Figure S3: Alignment of the amino acid sequence of NspF (accession number BAJ ) with the structurally characterized tyrosinases from Streptomyces castaneoglobisporus (1WX2_A) and Bacillus megaterium (3NTM_A). The copper binding His residues are indicated with asterisks, aliphatic to hydrogen bonding substitutions in the vicinity of the active site are indicated with plus signs, and the eleven residues following His39 in NspF are boxed.
5 SI 5 Figure S4: In the vicinity of the active site of S. castaneoglobisporus tyrosinase (PDB code 1WX2), two aliphatic residues in tyrosinase (Ile 42 and Ala 202 in white) are substituted by hydrogen bond acceptors (Asp 46 and Met 234, respectfully) in NspF. Two regions of low sequence similarity are also observed; the region after His38 (residue numbering from S. castaneoglobisporus tyrosinase) and a loop near the active site. References: 1. Noguchi A, Kitamura T, naka H, Horinouchi S, & hnishi Y (2010) A copper-containing oxidase catalyzes C-nitrosation in nitrosobenzamide biosynthesis. Nat. Chem. Biol. 6:
Supplementary Figure S1 Stable structures of I, I', II, and II' optimized at the
H C Si 2.492 (2.348) 1.867 (2.005) Fe O 2.106 (2.077) 2.360 (2.497) N 1.126 (1.115) 2.105 (2.175) I quintet (triplet) 0.0 (+4.1) kcal/mol II triplet (quintet) 0.0 (+4.3) kcal/mol 1.857 (2.076) 2.536 (2.351)
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