Schroeder Susanne, Lawrence Andrew D, Biedendieck Rebekka, Rose Ruth-Sarah, Deery Evelyne, Graham Ross M, McLean Kirsty J, Munro Andrew W, Rigby Stephen E J, Warren Martin J
Protein Science Group, Department of Biosciences, University of Kent, Canterbury, Kent CT27NJ, United Kingdom.
J Biol Chem. 2009 Feb 20;284(8):4796-805. doi: 10.1074/jbc.M807184200. Epub 2008 Dec 8.
The ring contraction process that occurs during cobalamin (vitamin B(12)) biosynthesis is mediated via the action of two enzymes, CobG and CobJ. The first of these generates a tertiary alcohol at the C-20 position of precorrin-3A by functioning as a monooxygenase, a reaction that also forms a gamma lactone with the acetic acid side chain on ring A. The product, precorrin-3B, is then acted upon by CobJ, which methylates at the C-17 position and promotes ring contraction of the macrocycle by catalyzing a masked pinacol rearrangement. Here, we report the characterization of CobG enzymes from Pseudomonas denitrificans and Brucella melitensis. We show that both contain a [4Fe-4S] center as well as a mononuclear non-heme iron. Although both enzymes are active in vivo, the P. denitrificans enzyme was found to be inactive in vitro. Further analysis of this enzyme revealed that the mononuclear non-heme iron was not reducible, and it was concluded that it is rapidly inactivated once it is released from the bacterial cell. In contrast, the B. melitensis enzyme was found to be fully active in vitro and the mononuclear non-heme iron was reducible by dithionite. The reduced mononuclear non-heme was able to react with the oxygen analogue NO, but only in the presence of the substrate precorrin-3A. The cysteine residues responsible for binding the Fe-S center were identified by site-directed mutagenesis. A mechanism for CobG is presented.
在钴胺素(维生素B12)生物合成过程中发生的环收缩过程是由两种酶CobG和CobJ介导的。其中第一种酶作为单加氧酶,在预咕啉-3A的C-20位生成叔醇,该反应还与A环上的乙酸侧链形成γ-内酯。产物预咕啉-3B随后由CobJ作用,CobJ在C-17位进行甲基化,并通过催化隐蔽的频哪醇重排促进大环的环收缩。在此,我们报道了反硝化假单胞菌和羊布鲁氏菌中CobG酶的特性。我们表明,这两种酶都含有一个[4Fe-4S]中心以及一个单核非血红素铁。尽管这两种酶在体内都有活性,但发现反硝化假单胞菌的酶在体外无活性。对该酶的进一步分析表明,单核非血红素铁不可还原,得出的结论是,一旦它从细菌细胞中释放出来就会迅速失活。相比之下,发现羊布鲁氏菌的酶在体外完全有活性,并且单核非血红素铁可被连二亚硫酸盐还原。还原的单核非血红素能够与氧类似物NO反应,但仅在底物预咕啉-3A存在的情况下。通过定点诱变确定了负责结合Fe-S中心的半胱氨酸残基。提出了CobG的作用机制。