A, vanadium site of native V-ClPO from C. inaequalis. Possible hydrogen bonds are drawn as dashed lines (adapted from Refs. 37–38 and 43). B, proposed catalytic scheme of V-ClPO (adapted from Refs. 38, 45, and 46).

Relatedness of V-BrPOs, V-ClPOs, and acid phosphatases identified in fungi, algae, and bacteria and some of their associated chemistry. Phylogenetic analysis was performed using ClustalW (56), and the unrooted neighbor-joining tree was visualized by TreeView. The scale bar indicates 0.1 changes per amino acid. Sequence identification codes include Ci_VClPO from C. inaequalis (accession number CAA59686), hypothetical Rb_VClPO from Rhodopirellula baltica SH1 (CAD72609), Ed_VClPO from E. didymospora (CAA72622), hypothetical Ss1_VClPO from Streptomyces sp. CNQ-525 (ABS50486), hypothetical Ss3_VClPO from Streptomyces sp. CNQ-525 (ABS50491), hypothetical Ss4_VClPO from Streptomyces sp. CNQ-525 (ABS50492), hypothetical Cs_VClPO from Cellulophaga sp. MED134 (ZP_01050453), An_VBrPO from A. nodosum (P81701), Co_VBrPO from C. officinalis (AAM46061), Cp1_VBrPO from C. pilulifera (BAA31261), Cp2_VBrPO from C. pilulifera (BAA31262), hypothetical Sys_VBrPO from Synechococcus sp. CC9311 (YP_731869), Fd_VBrPO from Fucus distichus (AAC35279), Ld1_VBrPO from L. digitata (CAD37191), Ld2_VBrPO from L. digitata (CAD37192), Pi_ACP acid phosphatase from Prevotella intermedia (AB017537), Kp_ACP acid phosphatase from Klebsiella pneumonia (AJ250377), St_ACP acid phosphatase from Salmonella typhimurium (X63599), Ps_ACP acid phosphatase from Providencia stuartii (X64820), and Eb_ACP acid phosphatase from Escherichia blattae (AB020481). Halogenated natural products are α-snyderol (2), β-snyderol (3), γ-snyderol (4), and A80915C (6). Proposed substrates for V-HPOs are (E)-(+)-nerolidol (1) and SF2415B1 (5).