• 特约评述 •
夏孔晨, 徐维华, 吴起
收稿日期:
2024-01-25
修回日期:
2024-04-28
出版日期:
2024-05-15
通讯作者:
徐维华,吴起
作者简介:
基金资助:
Kongchen XIA, Weihua XU, Qi WU
Received:
2024-01-25
Revised:
2024-04-28
Online:
2024-05-15
Contact:
Weihua XU, Qi WU
摘要:
光催化具有条件温和、可再生、反应性强等优点,然而由于自由基的高活性往往导致其选择性难以调控,从而限制了光催化在不对称有机合成中的广泛应用。酶催化虽具有高选择性和专一性的优势,但这也导致其存在反应类型单一和底物谱窄等缺陷。将反应性强的光催化与选择性高的酶催化相结合的光酶催化则可以提供一种全新的合成模式,实现优势互补,更加符合现代绿色有机合成的要求。狭义的光酶催化反应,也就是光酶协同反应一般包括以下四类:天然光酶反应,人工光酶反应,光催化与酶催化的偶联反应以及光酶催化混乱性反应。近年来,光酶催化的研究蓬勃发展,解决了许多传统有机合成中难以实现的问题,尤其是在不对称合成领域已占据重要地位。例如,脂肪酸光脱酸酶可以催化长链脂肪酸脱羧转化为相应烃类;结合光敏辅因子和蛋白骨架的人工光酶大大拓展了酶的应用范围,催化更多样化非天然有机化学品的生物合成;光催化剂催化光化学反应与通常酶催化反应的偶联方式可以实现一些复杂的有机合成过程;以及近年来一些含有光敏辅因子的氧化还原酶在光激发下催化新分子混乱性反应的功能。尽管已有许多文献对相关研究进行了总结,但是自2023年以来,光酶催化混乱性研究不断突破,涌现出许多全新的光酶催化反应类型和反应机理,立体选择性和区域选择性的精准调控更是满足了不对称合成的重大需求。对于这个飞速发展的领域,系统归纳其成果仍显得至关重要。因此本综述聚焦在光激发下光敏辅因子依赖型酶催化的混乱性反应最新研究成果, 根据不同催化反应类型,分别介绍光酶通过自由基途径实现不对称脱卤、氢化、分子内环化、分子间C-C/C-N/C-S键交叉耦合等非天然反应。这些反应由于酶和底物的不同,展示了不同机理。例如在氧化还原起始过程中,包括单电子还原起始和单电子氧化起始两种类型;在自由基终止过程中,可能采用单电子还原终止和单电子氧化终止,而单电子还原终止方式中也存在氢原子转移和电子转移/质子转移耦合过程等不同情况。机理的多样性也为拓展更多的光酶催化混乱性反应提供了可能。在未来,新型的光酶催化方法将在快速发展的基因工程、合成生物学、酶工程,以及流动化学、人工智能等学科和技术的推动下,涌现出更多高效、高选择性的新分子新功能反应,显著拓展光酶催化方法在有机合成,尤其是绿色不对称合成领域中的应用范围。
中图分类号:
夏孔晨, 徐维华, 吴起. 光酶催化混乱性反应的研究进展[J]. 合成生物学, DOI: 10.12211/2096-8280.2024-012.
Kongchen XIA, Weihua XU, Qi WU. Recent advances in photo-induced promiscuous enzymatic reactions[J]. Synthetic Biology Journal, DOI: 10.12211/2096-8280.2024-012.
图2 酶促自由基脱卤/脱乙酰氧基(a) GluER催化自由基脱卤;(b) 光诱导NtDBR催化自由基脱乙酰氧基
Fig. 2 Enzymatic radical dehalogenation/ decarboxylation(a) Radical dehalogenation catalyzed by GluER; (b) Photo-induced radical decarboxylation catalyzed by NtDBR
图4 光诱导酶促羰基自由基不对称氢化(a) 光诱导MorB催化羰基自由基不对称氢化;(b) 光诱导BaNTR1催化羰基自由基不对称氢化
Fig. 4 Photo-induced enzymatic enantioselective ketone reduction(a) Photo-induced enantioselective ketone reduction catalyzed by MorB; (b) Photo-induced enantioselective ketone reduction catalyzed by BaNTR1
图5 光诱导酶促烯烃不对称氢化(a) 光诱导NostocER催化烯烃不对称氢化;(b) 光诱导EREDs催化烯烃不对称氢化
Fig. 5 Photo-induced enzymatic enantioselective radical hydroalkylation of alkenes(a) Photo-induced enantioselective radical hydroalkylation of alkenes catalyzed by NostocER; (b) Photo-induced enantioselective radical hydroalkylation of alkenes catalyzed by EREDs;
图6 光诱导酶促自由基分子内环化(a) 光诱导EREDs催化自由基分子内环化;(b) 光诱导GluER催化自由基分子内环化;(c) 光诱导GluERW100H催化自由基分子内环化
Fig. 6 Photo-induced enzymatic intramolecular cyclization(a) Photo-induced intramolecular cyclization catalyzed by EREDs; (b) Photo-induced intramolecular cyclization catalyzed by GluER; (c) Photo-induced intramolecular cyclization catalyzed by GluERW100H
图7 光诱导酶促缺电子自由基对烯烃的不对称氢烷基化反应(a) 光诱导EREDs催化氢烷基化反应;(b) 光诱导MorB催化氢烷基化反应;(c) 光诱导OYE1催化氢烷基化反应;(d) 光诱导EREDs催化氢烷基化反应
Fig. 7 Photo-induced enzymatic enantioselective radical hydrogen alkylation of olefins by electron-deficient radicals(a) Photo-induced hydrogen alkylation of olefins catalyzed by EREDs; (b) Photo-induced hydrogen alkylation of olefins catalyzed by MorB; (c) Photo-induced hydrogen alkylation of olefins catalyzed by OYE1; (d) Photo-induced hydrogen alkylation of olefins catalyzed by EREDs
图8 光诱导酶促富电子自由基对不饱和键的不对称加成反应(a) 光诱导KRED催化不饱和键的加成反应;(b) 光诱导RasADH催化不饱和键的加成反应;(c) 光诱导EREDs催化不饱和键的加成反应
Fig. 8 Photo-induced enzymatic enantioselective addition of electron-rich radicals to unsaturated bonds(a) Photo-induced addition reaction to unsaturated bonds catalyzed by KRED; (b) Photo-induced addition reaction to unsaturated bonds catalyzed by RasADH; (c) Photo-induced addition reaction to unsaturated bonds catalyzed by EDEDs
图10 光诱导酶促对映选择性C(sp3 )-C(sp3 )交叉亲电偶联(a) 光诱导GluER/CsER催化对映选择性C(sp3 )-C(sp3 )交叉亲电偶联;(b) 光诱导GkOYE催化对映选择性C(sp3 )-C(sp3 )交叉亲电偶联
Fig. 10 Photo-induced enzymatic enantioselective C(sp3 )-C(sp3 ) XECs(a) Photo-induced enantioselective C(sp3 )-C(sp3 ) XECs catalyzed by GluER/CsER; (b) Photo-induced C(sp3 )-C(sp3 ) XECs catalyzed by GkOYE
图12 光诱导酶促不对称C-N键形成(a) 光诱导YqjM催化不对称C-N键形成;(b) 光诱导XenB催化不对称C-N键形成
Fig. 12 Photo-induced enzymatic formation of C-N bond(a) Photo-induced enantioselective C-N bond formation catalyzed by YqjM; (b) Photo-induced enantioselective C-N bond formation catalyzed by XenB
图8 光诱导酶促不对称C-S键形成(a) 光诱导OYE1催化不对称C-S键形成;(b) 光诱导GluERW100F/W342F催化不对称C-S键形成
Fig. 8 Photo-induced enzymatic enantioselective C-N/ C-S bond forming(a) Photo-induced enantioselective C-S bond forming catalyzed by OYE1; (b) Photo-induced enantioselective C-S bond forming catalyzed by GluERW100F/W342F
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