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LADA strategy for the synthesis of unnatural amino acids and direct modifications of peptides

Science China Chemistry 2023年第6期66卷 1788-1794页

作者： Jun-Liang Zhou Yun-Qi Liu Zhan-Kui Sun Shanghai Frontiers Science Center for Drug Target Identification and Drug Delivery School of Pharmaceutical SciencesShanghai Jiao Tong UniversityShanghai 200240China Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Pharm-X CenterSchool of Pharmaceutical SciencesShanghai Jiao Tong UniversityShanghai 200240China AI Pharma Center Zhangjiang Institute for Advanced StudyShanghai Jiao Tong UniversityShanghai 200240China Shanghai Artificial Intelligence Laboratory Shanghai 200232China

unnatural amino acids(UAAs)are important building blocks in organic synthesis and drug *** are also frequently integrated into peptides or proteins for biological ***,the direct and simplified synthesis of UAAs remains a great *** the same time,vast known peptide modifications are based on carbon-heteroatom *** are no general methods for peptide modifications via the construction of C–C *** address this challenge,herein we propose the LADA strategy,which is composed of two steps:the selective labeling and activation of cysteine residues,the desulfurization to generate carbon-centered radical and the radical addition to alkenes to build C–C *** one-pot protocol has obvious advantages such as good functional group tolerance,biocompatible reaction conditions,and retained *** strategy was successfully utilized for the synthesis of unnatural amino acids and direct modifications of peptides.

关键词： unnatural amino acids peptide modifications desulfurization cysteine radical addition

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Direct synthesis of unnatural amino acids and modifications of peptides via LADA strategy

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Chinese Chemical Letters 2024年第1期35卷 237-242页

作者： Yunqi Liu Junliang Zhou Zhankui Sun Shanghai Frontiers Science Center for Drug Target Identification and Drug Delivery School of Pharmaceutical SciencesShanghai Jiao Tong UniversityShanghai 200240China Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Pharm-X CenterSchool of Pharmaceutical SciencesShanghai Jiao Tong UniversityShanghai 200240China AI Pharma Center Zhangjiang Institute for Advanced StudyShanghai Jiao Tong UniversityShanghai 201203China Shanghai Artificial Intelligence Laboratory Shanghai 200232China

unnatural amino acids(UAAs)have broad applications in pharmaceutical sciences and biological *** synthetic methods for UAAs mainly rely on asymmetric catalysis and often require several *** is a lack of direct and simple *** address this challenge,we designed the LADA(labeling-activation-desulfurization-addition)strategy:selective labeling and activation of cysteine residues,the photocatalytic desulfurization and the subsequent radical addition to *** composed of two steps,it is one-pot synthesis and has advantages such as high functional group tolerance,biocompatible reaction condition,and retained *** highly efficient strategy was successfully applied in the direct synthesis of unnatural amino acids and modifications of peptides with more than 50 examples.

关键词： unnatural amino acids Peptide modifications Desulfurization Cysteine Radical addition

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A linear DNA template-based framework for site-specific unnatural amino acid incorporation

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Synthetic and Systems Biotechnology 2021年第3期6卷 192-199页

作者： Xinjie Chen Yingying Liu Jiaqi Hou Yuan Lu Key Laboratory of Industrial Biocatalysis Ministry of EducationDepartment of Chemical EngineeringTsinghua UniversityBeijing100084China

Site-specific incorporation of unnatural amino acids(UNAAs)into proteins using an orthogonal translation system(OTS)has expanded the scope of protein-coding *** key factor affecting UNAA embedding efficiency is the orthogonality of the *** to traditional cell systems,cell-free systems are more convenient to control the reaction process and improve the utilization rate of *** this study,a linear DNA template-based cell-free unnatural protein synthesis system for rapid high-throughput screening and evolution was proposed.A total of 14 cell extracts were selected for screening out cell extract with high expression *** result showed that EcAR7ΔAΔSer cell extract was optimal for the cell-free *** addition,the screening results of four UNAAs,p-propargyloxy-l-phenylalanine(pPaF),p-azyl-phenylalanine(pAzF),p-acetyl-l-phenylalanine(pAcF),and p-benzoyl-l-phenylalanine(pBpF),showed that o-aaRS and o-tRNA of pPaF had good orthogonality.A new pair of corresponding o-aaRS and o-tRNA for pBpF was screened *** results proved that this method could speed up the screening of optimal OTS components for UNAAs with versatile functions.

关键词： Cell-free protein synthesis Linear PCR product Rapid screening unnatural amino acids

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Cell-free synthetic biology:Engineering in an open world

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Synthetic and Systems Biotechnology 2017年第1期2卷 23-27页

作者： Yuan Lu Key Lab of Industrial Biocatalysis Ministry of EducationDepartment of Chemical EngineeringTsinghua UniversityBeijing 100084China Institute of Biochemical Engineering Department of Chemical EngineeringTsinghua UniversityBeijing 100084China

Cell-free synthetic biology emerges as a powerful and flexible enabling technology that can engineer biological parts and systems for life science applications without using living *** provides simpler and faster engineering solutions with an unprecedented freedom of design in an open environment than cell *** review focuses on recent developments of cell-free synthetic biology on biological engineering fields at molecular and cellular levels,including protein engineering,metabolic engineering,and artificial cell *** cell-free protein engineering,the direct control of reaction conditions in cell-free system allows for easy synthesis of complex proteins,toxic proteins,membrane proteins,and novel proteins with unnatural amino ***-free systems offer the ability to design metabolic pathways towards the production of desired *** of artificial cells based on cell-free systems will improve our understanding of life and use them for environmental and biomedical applications.

关键词： Cell-free synthetic biology Cell-free protein synthesis Protein engineering Metabolic engineering Artificial cell unnatural amino acids

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Significant expansion and red-shifting of fluorescent protein chromophore determined through computational design and genetic code expansion

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Biophysics Reports 2018年第5期4卷 273-285页

作者： Li Wang Xian Chen Xuzhen Guo Jiasong Li Qi Liu Fuying Kang Xudong Wang Cheng Hu Haiping Liu Weimin Gong Wei Zhuang Xiaohong Liu Jiangyun Wang Institute of Biophysics Chinese Academy of Sciences College of Life Sciences University of Chinese Academy of Sciences Key Laboratory of Physics and Technology for Advanced Batteries (Ministry of Education) Department of PhysicsJilin University State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences

Fluorescent proteins(FPs) with emission wavelengths in the far-red and infrared regions of the spectrum provide powerful tools for deep-tissue and super-resolution imaging. The development of red-shifted FPs has evoked widespread interest and continuous engineering efforts. In this article,based on a computational design and genetic code expansion, we report a rational approach to significantly expand and red-shift the chromophore of green fluorescent protein(GFP). We applied computational calculations to predict the excitation and emission wavelengths of a FP chromophore harboring unnatural amino acids(UAA) and identify in silico an appropriate UAA, 2-amino-3-(6-hydroxynaphthalen-2-yl)propanoic acid(naphthol-Ala). Our methodology allowed us to formulate a GFP variant(cpsf GFP-66-Naphthol-Ala) with red-shifted absorbance and emission spectral maxima exceeding 60 and 130 nm, respectively, compared to those of GFP. The GFP chromophore is formed through autocatalytic post-translational modification to generate a planar 4-(p-hydroxybenzylidene)-5-imidazolinone chromophore. We solved the crystal structure of cpsf GFP-66-naphthol-Ala at 1.3 ? resolution and demonstrated the formation of a much larger conjugated p-system when the phenol group is replaced by naphthol. These results explain the significant red-shifting of the excitation and emission spectra of cpsf GFP-66-naphthol-Ala.

关键词： Computational design Green fluorescent protein Red-shift unnatural amino acids

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A New Class of Highly Potent and Selective Endomorphin-1 Analogues Containing α-Methylene-β-aminopropanoic acids(Map)

A New Class of Highly Potent and Selective Endomorphin-1 Ana...

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第十一届全国博士生学术年会

作者： Yuan Wang Yanhong Xing Xin Liu Rui Wang Key Laboratory of Preclinical Study for New Drugs of Gansu Province School of Basic Medical Sciencesand Institute of Biochemistry and Molecular BiologySchool of Life SciencesLanzhou University

In this paper a new class of endomorphin-l(EM-1) analogues were synthesized by introduction of novel unnatural a-methylene-β-amino acids(Map) at position 3 or/and *** binding and functional activity,metabolic stability and antinociceptive activity were determined and *** of these analogues showed high affinities for the/t-opioid receptor and an increased stability in mouse brain homogenates than *** of cAMP accumulation and EKR1/2 phosphorylation in HEK293 cells confirmed the agonist properties of these *** found that,compared to EM-1,the incorporation of our synthesized Map at position 4 would bring the analogue to a closer binding mode with theμ-opioid receptor.

关键词： antinociception endomorphin-1 functional activity opioid peptide structure-activity relationships unnatural amino acids

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Expanding the Genetic Code

Expanding the Genetic Code

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第二届全国“跨学科蛋白质研究”学术讨论会

作者：王江云 Institute of Biophysics Chinese Academy of Sciences

By engineering t-RNA and t-RNA synthetase,I have first genetically incorporated fluorescent amino acids in *** are now using these environmentally sensitive fluorescent amino acids to probe enzyme mechanism,protein folding,and protein-protein ***,because the fluorescent amino acids are pH sensitive,they are incorporated into cytokines to probe the kinetics of cytokine endocytosis process.

关键词： genetic code expansion unnatural amino acids

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Expanding the genetic code of Pseudomonas aeruginosa

Expanding the genetic code of Pseudomonas aeruginosa

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第十届全国化学生物学学术会议

作者： Huangtao Zheng Shixian Lin Peng R Chen Beijing National Laboratory for Molecular Sciences College of Chemistry and Molecular EngineeringPeking University

The genetic code expansion strategy, which incorporates unnatural amino acids with diverse functionalities into specific sites of target proteins, has been proved to facilitate biological study in many organisms. Here we have extended the pyrrolysine-based genetic code expansion strategy in Pseudomonas aeruginosa（PA）, a common opportunistic human pathogen. Using this system, a photo-crosslinking amino acid was incorporated into type III secretion effector ExoS, which allowed the identification of its interaction proteins. Additionally, an azide-bearing amino acid was introduced into PA flagellin, FliC. which allowed in vivo labeling and imaging of PA flagella. This work will provide powerful tools for a wide range of studies on Pseudomonas aeruginosa.

关键词： Genetic code expansion unnatural amino acids Pseudomonas aeruginosa Bacterial pathogen

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Chemical tags and beyond:Live-cell protein labeling technologies for modern optical imaging

Smart Molecules

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Smart Molecules 2023年第2期1卷 16-29页

作者： Dilizhatai Saimi Zhixing Chen College of Future Technology Institute of Molecular MedicineNational Biomedical Imaging CenterBeijing Key Laboratory of Cardiometabolic Molecular MedicinePeking UniversityBeijingChina Peking-Tsinghua Center for Life Science Academy for Advanced Interdisciplinary StudiesPeking UniversityBeijingChina

Imaging proteins with high resolution is crucial for studying cellular physiology and *** imaging is a privileged method to visualize proteins with subcellular precision in live *** recent years,there has been a tremendous advance in the field of fluorescent dyes that are optically more sophisticated than genetically-encodable fluorescent *** this review,we aim to discuss modern bioconjugation methods to specifically incorporate these dyes into *** focus on advances in live-cell labeling strategies and fluorescent probes,especially the HaloTag,SNAP-tag,TMP-tag,and unnatural amino acid systems and their *** protein labeling methods,along with cutting-edge dyes and novel microscopy methods,have become the infrastructure for biological research in the era of super-resolution imaging.

关键词： fluorescent dyes live-cell imaging protein labeling self-labeling tags unnatural amino acids

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