Engineering metalloenzymes for new-to-nature carbene and nitrene transfer biocatalysis

doi:10.1016/S1872-2067(25)64659-6

Chinese Journal of Catalysis ›› 2025, Vol. 72: 4-23.DOI: 10.1016/S1872-2067(25)64659-6

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Engineering metalloenzymes for new-to-nature carbene and nitrene transfer biocatalysis

Wenjin Pan^a^,¹, Xinlong Fan^a^,¹, Wantong Jiang^b, Sirui Xin^c, Ningzhi Wang^d, Qian Wang^e, Keyang Yu^a, Xinkun Ren^a^,^*()

^aCollege of Engineering and Applied Sciences, National Laboratory of Solid State Microstructures, Nanjing University, Nanjing 210023, Jiangsu, China
^bSchool of Life Sciences, Nanjing University, Nanjing 210023, Jiangsu, China
^cSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, Jiangsu, China
^dKuang Yaming Honors School, Nanjing University, Nanjing 210023, Jiangsu, China
^eSchool of Environment, Nanjing University, Nanjing 210023, Jiangsu, China

Received:2024-11-05 Accepted:2025-01-14 Online:2025-05-18 Published:2025-05-20
Contact: *E-mail: xinkunren@nju.edu.cn (X. Ren).
About author:Xinkun Ren (College of Engineering and Applied Sciences, Nanjing University) received his B.A. degree from Kuang Yaming Honors School, Nanjing University (P. R. China) in 2012, and Ph.D. degree from University of Oxford (United Kingdom) in 2018. He carried out his Postdoctoral research at University of Rochester from 2018 to the end of 2021. Since then, he has been working in College of Engineering of Applied Sciences (P. R. China). He is a recipient of the National Natural Science Foundation's Overseas Outstanding Youth Program (2022) and Distinguished Young Scholar of Natural Science Foundation of Jiangsu Province (2023). His current research focuses on new synthetic strategies, mechanisms, and applications of biocatalysts, aiming to overcome the limitations of natural evolution. He has published more than 20 peer-reviewed papers and served as primary inventor in filling over 40 invention patents.
First author contact:¹These authors contributed equally.
Supported by:
Natural Science Foundation of Jiangsu Province(BK20232017);Science Fund for Distinguished Young Scholars of Jiangsu Province(BK20230022)

Abstract

Abstract:

Biocatalysis, which involves using enzymes to address synthetic challenges of significance to humans, has rapidly developed into a pivotal technology for chemical innovation. Over the past decade, there has been a notable increase in the use of metalloproteins as catalysts for abiotic, synthetically valuable carbene and nitrene transfer reactions. This trend highlights the adaptability of protein-based catalysts and our growing ability to harness this potential for novel enzyme chemistry. This review focuses on the most recent advancements in metalloenzyme-catalyzed carbene and nitrene transfer reactions, including cyclopropanation, carbene Y-H and C-H insertions, Doyle-Kirmse reactions, aldehyde olefinations, nitrene azide-to-aldehyde conversions, and nitrene C-H insertion. A variety of protein scaffolds have been engineered to offer varied levels of reactivity and selectivity towards pharmaceutically relevant compounds. The application of these new catalysts in preparative-scale synthesis underscores their emerging biotechnological significance. Furthermore, insights into key intermediate and determining factors in stereochemistry are offering valuable guidance for engineering metalloproteins, thereby expanding the scope and utility of these non-natural activities.

Key words: Metalloenzyme, Biocatalysis, Carbene, Nitrene, Non-natural reaction

Wenjin Pan, Xinlong Fan, Wantong Jiang, Sirui Xin, Ningzhi Wang, Qian Wang, Keyang Yu, Xinkun Ren. Engineering metalloenzymes for new-to-nature carbene and nitrene transfer biocatalysis[J]. Chinese Journal of Catalysis, 2025, 72: 4-23.

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Figures/Tables 14

Fig. 1. Structural similarity of Fe-oxene, carbene, and nitrene complexes.

Fig. 2. The emergence of biocatalytic carbene and nitrene transfer reactions.

Fig. 3. Overview of key advances in carbene precursors for inter- and intramolecular biocatalytic cyclopropanation.

Table 1 Comparison of intermolecular biocatalytic cyclopropanation reactions with key carbene donors and acceptors.

Entry	Enzyme Variant	Conversion (concentration)	Cis:trans	Ee^a (%)	TON	Ref. ^b
1	P411BM3-CIS	72% (170 mmol/L)	90:10	99	67800	[14]
2	Mb H64V/V68A	99% (200 mmol/L)	0.05:99.95	99.9	10000	[15]
3	Mb RR5	53% (10 mmol/L)	0.5:99.5	95	265	[22]
4	Mb H64V/V68A	99% (30 mmol/L)	0.05:99.95	99.9	500	[23]
5	Mb RR2	92% (30 mmol/L)	0.05:99.5	99.9	1110	[26]
6	ApePgb W59L/Y60Q	30% (10 mmol/L)	97:3	89	560	[25]
7	Mb H64V/V68A	85% (30 mmol/L)	0.05:99.95	99.9	5600	[24]
8	P411-G8S	~45% (10 mmol/L)	0.5:99.5	98.3	3090	[27]
9	Mb H64G/V68A	99% (2.5 mmol/L)	0.5:99.5	99	250	[28]
10	ApePgb GLAVRSQLL	53% (10 mmol/L)	6.9:1	60	106	[29]
11	Mb H64G/V68A	99% (10 mmol/L)	0.5:99.5	99	250	[30]
12	Mb RR4	96% (5 mmol/L)	0.5:99.5	99	92	[30]
13	Mb H64V/V68A	98% (10 mmol/L)	2:98	98	490	[31]
14	Mb VVVF	73% (10 mmol/L)	2:98	96	365	[31]

Fig. 4. Selected examples on expanding carbene acceptors for biocatalytic cyclopropanation reactions.

Fig. 5. Selected examples of artificial metalloprotein for carbene transfer cyclopropanation reactions.

Fig. 6. Stereoselective synthesis of cyclopropane-containing drug intermediates by engineered carbene transferases.

Fig. 7. Selected examples of biocatalytic carbene Y-H insertion reactions.

Fig. 8. Selected examples of biocatalytic carbene C-H insertion reactions.

Fig. 9. Selected examples of other type of biocatalytic carbene transfer reactions.

Fig. 10. Selected examples of intramolecular nitrene C-H amination reactions.

Fig. 11. Selected examples of intermolecular nitrene C-H amination reactions.

Fig. 12. Biocatalytic nitrene transfer aziridination and aminohydroxylation.

Fig. 13. Selected examples of other types of nitrene transfer reactions.

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Engineering metalloenzymes for new-to-nature carbene and nitrene transfer biocatalysis

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