Stereoselective amino acid synthesis by synergistic photoredox-pyridoxal radical biocatalysis

被引：59

作者：

Cheng, Lei ^{[1
]}

Li, Dian ^{[1
]}

Mai, Binh Khanh ^{[2
]}

Bo, Zhiyu ^{[1
]}

Cheng, Lida ^{[1
]}

Liu, Peng ^{[2
]}

Yang, Yang ^{[1
,3
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[3] Univ Calif Santa Barbara, Biomol Sci & Engn BMSE Program, Santa Barbara, CA 93106 USA

来源：

SCIENCE | 2023年 / 381卷 / 6656期

基金：

美国国家卫生研究院;

关键词：

ASYMMETRIC-SYNTHESIS; DIRECTED EVOLUTION; ENZYMES; PATHWAYS; TOOLBOX; CARBENE; ACCESS;

D O I：

10.1126/science.adg2420

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Developing synthetically useful enzymatic reactions that are not known in biochemistry and organic chemistry is an important challenge in biocatalysis. Through the synergistic merger of photoredox catalysis and pyridoxal 5'-phosphate (PLP) biocatalysis, we developed a pyridoxal radical biocatalysis approach to prepare valuable noncanonical amino acids, including those bearing a stereochemical dyad or triad, without the need for protecting groups. Using engineered PLP enzymes, either enantiomeric product could be produced in a biocatalyst-controlled fashion. Synergistic photoredox-pyridoxal radical biocatalysis represents a powerful platform with which to discover previously unknown catalytic reactions and to tame radical intermediates for asymmetric catalysis.

引用

页码：444 / 451

页数：8

共 60 条

[1] Free Energies of Proton-Coupled Electron Transfer Reagents and Their Applications
Agarwal, Rishi G.
Coste, Scott C.
Groff, Benjamin D.
Heuer, Abigail M.
Noh, Hyunho
Parada, Giovanny A.
Wise, Catherine F.
Nichols, Eva M.
Warren, Jeffrey J.
Mayer, James M.
[J]. CHEMICAL REVIEWS, 2022, 122 (01) : 1 - 49
[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development
Allen, Anna E.
MacMillan, David W. C.
[J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
[3] Engineering enzymes for noncanonical amino acid synthesis
Almhjell, Patrick J.
Boville, Christina E.
Arnold, Frances H.
[J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (24) : 8980 - 8997
[4] Marfey's reagent for chiral amino acid analysis:: A review
Bhushan, R
Brückner, H
[J]. AMINO ACIDS, 2004, 27 (3-4) : 231 - 247
[5] Photoexcitation of flavoenzymes enables a stereoselective radical cyclization
Biegasiewicz, Kyle F.
Cooper, Simon J.
Gao, Xin
Oblinsky, Daniel G.
Kim, Ji Bye
Garfinkle, Samuel E.
Joyce, Leo A.
Sandoval, Braddock A.
Scholes, Gregory D.
Hyster, Todd K.
[J]. SCIENCE, 2019, 364 (6446) : 1166 - +
[6] Exploiting and engineering hemoproteins for abiological carbene and nitrene transfer reactions
Brandenberg, Oliver F.
Fasan, Rudi
Arnold, Frances H.
[J]. CURRENT OPINION IN BIOTECHNOLOGY, 2017, 47 : 102 - 111
[7] Directed Evolution Mimics Allosteric Activation by Stepwise Tuning of the Conformational Ensemble
Buller, Andrew R.
van Roye, Paul
Cahn, Jackson K. B.
Scheele, Remkes A.
Herger, Michael
Arnold, Frances H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (23) : 7256 - 7266
[8] Directed evolution of the tryptophan synthase β-subunit for stand-alone function recapitulates allosteric activation
Buller, Andrew R.
Brinkmann-Chen, Sabine
Romney, David K.
Herger, Michael
Murciano-Calles, Javier
Arnold, Frances H.
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2015, 112 (47) : 14599 - 14604
[9] Engineering new catalytic activities in enzymes
Chen, Kai
Arnold, Frances H.
[J]. NATURE CATALYSIS, 2020, 3 (03) : 203 - 213
[10] Discovery and Biocatalytic Application of a PLP-Dependent Amino Acid γ-Substitution Enzyme That Catalyzes C-C Bond Formation
Chen, Mengbin
Liu, Chun-Ting
Tang, Yi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (23) : 10506 - 10515

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