Carey James R, Ma Steven K, Pfister Thomas D, Garner Dewain K, Kim Hyeon K, Abramite Joseph A, Wang Zhilin, Guo Zijian, Lu Yi
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
J Am Chem Soc. 2004 Sep 8;126(35):10812-3. doi: 10.1021/ja046908x.
Introducing nonnative metal ions or metal-containing prosthetic groups into a protein can dramatically expand the repertoire of its functionalities and thus its range of applications. Particularly challenging is the control of substrate-binding and thus reaction selectivity such as enantioselectivity. To meet this challenge, both non-covalent and single-point attachments of metal complexes have been demonstrated previously. Since the protein template did not evolve to bind artificial metal complexes tightly in a single conformation, efforts to restrict conformational freedom by modifying the metal complexes and/or the protein are required to achieve high enantioselectivity using the above two strategies. Here we report a novel site-selective dual anchoring (two-point covalent attachment) strategy to introduce an achiral manganese salen complex (Mn(salen)), into apo sperm whale myoglobin (Mb) with bioconjugation yield close to 100%. The enantioselective excess increases from 0.3% for non-covalent, to 12.3% for single point, and to 51.3% for dual anchoring attachments. The dual anchoring method has the advantage of restricting the conformational freedom of the metal complex in the protein and can be generally applied to protein incorporation of other metal complexes with minimal structural modification to either the metal complex or the protein.
将非天然金属离子或含金属的辅基引入蛋白质中,可以显著扩展其功能范围,进而扩大其应用范围。特别具有挑战性的是控制底物结合,从而控制反应选择性,如对映选择性。为应对这一挑战,此前已证明了金属配合物的非共价和单点连接方法。由于蛋白质模板并非进化为以单一构象紧密结合人工金属配合物,因此需要通过修饰金属配合物和/或蛋白质来限制构象自由度,以利用上述两种策略实现高对映选择性。在此,我们报告了一种新颖的位点选择性双锚定(两点共价连接)策略,即将一种非手性锰卟啉配合物(Mn(salen))引入脱辅基抹香鲸肌红蛋白(Mb)中,生物共轭产率接近100%。对映体过量从非共价连接的0.3%增加到单点连接的12.3%,再到双锚定连接的51.3%。双锚定方法具有限制蛋白质中金属配合物构象自由度的优点,并且可以在对金属配合物或蛋白质进行最小结构修饰的情况下,普遍应用于其他金属配合物与蛋白质的结合。