ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Residue-Specific Peptide Modification: A Chemist’s Guide

View Author Information
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
Cite this: Biochemistry 2017, 56, 30, 3863–3873
Publication Date (Web):June 27, 2017
Copyright © 2017 American Chemical Society

    Article Views





    Read OnlinePDF (10 MB)
    Supporting Info (1)»


    Abstract Image

    Advances in bioconjugation and native protein modification are appearing at a blistering pace, making it increasingly time consuming for practitioners to identify the best chemical method for modifying a specific amino acid residue in a complex setting. The purpose of this perspective is to provide an informative, graphically rich manual highlighting significant advances in the field over the past decade. This guide will help triage candidate methods for peptide alteration and will serve as a starting point for those seeking to solve long-standing challenges.

    Supporting Information

    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.biochem.7b00536.

    • Delineation of Amino Acid Side-Chain Modification Report Card assessments, including references (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system:

    Cited By

    This article is cited by 356 publications.

    1. Feng Gao, Mengyang Chang, Xiang Meng, Hang Xu, Giri Gnawali, Yue Dong, Byrdie Lopez, Wei Wang. Site-Selective Modification of Secondary Amine Moieties on Native Peptides, Proteins, and Natural Products with Ynones. Bioconjugate Chemistry 2023, 34 (9) , 1553-1562.
    2. Chao Wang, Rupeng Qi, Rui Wang, Zhaoqing Xu. Photoinduced C(sp3)–H Functionalization of Glycine Derivatives: Preparation of Unnatural α-Amino Acids and Late-Stage Modification of Peptides. Accounts of Chemical Research 2023, 56 (15) , 2110-2125.
    3. Joanna C. Lee, James D. Cuthbertson, Nicholas J. Mitchell. Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan. Organic Letters 2023, 25 (29) , 5459-5464.
    4. Weipeng Li, Yu Chen, Yinghan Chen, Siyu Xia, Wenju Chang, Chengjian Zhu, K. N. Houk, Yong Liang, Jin Xie. Site-Selective Arylation of Carboxamides from Unprotected Peptides. Journal of the American Chemical Society 2023, 145 (27) , 14865-14873.
    5. Cunyuan Zhao, Yuankai Wang, Quan Pham, Changhang Dai, Abhishek Chatterjee, Masayuki Wasa. Chemical Tagging of Bioactive Amides by Cooperative Catalysis: Applications in the Syntheses of Drug Conjugates. Journal of the American Chemical Society 2023, 145 (26) , 14233-14250.
    6. Peng Yang, Martynas J. Širvinskas, Bo Li, Nicholas W. Heller, Hua Rong, Gang He, Andrei K. Yudin, Gong Chen. Teraryl Braces in Macrocycles: Synthesis and Conformational Landscape Remodeling of Peptides. Journal of the American Chemical Society 2023, 145 (25) , 13968-13978.
    7. Carlota Girón-Elola, Ibon Sasiain, Rosalía Sánchez-Fernández, Elena Pazos, Arkaitz Correa. Site-Selective C–H Amination of Phenol-Containing Biomolecules. Organic Letters 2023, 25 (23) , 4383-4387.
    8. Jizhou Song, Takeru Torigoe, Yoichiro Kuninobu. Decatungstate-Catalyzed C(sp3)–H Alkylation of a Val Residue Proximal to the N-Terminus Controlled by an Electrostatic Interaction. Organic Letters 2023, 25 (20) , 3708-3712.
    9. E. Dalles Keyes, Marcus C. Mifflin, Maxwell J. Austin, Brighton J. Alvey, Lotfa H. Lovely, Andriea Smith, Tristin E. Rose, Bethany A. Buck-Koehntop, Jyoti Motwani, Andrew G. Roberts. Chemoselective, Oxidation-Induced Macrocyclization of Tyrosine-Containing Peptides. Journal of the American Chemical Society 2023, 145 (18) , 10071-10081.
    10. Liangliang Song, Zhenwei Lv, Yan Li, Kui Zhang, Erik V. Van der Eycken, Lingchao Cai. Construction of Peptide–Isoquinolone Conjugates via Rh(III)-Catalyzed C–H Activation/Annulation. Organic Letters 2023, 25 (17) , 2996-3000.
    11. Joshua M. Hammond, Michael G. Gardiner, Lara R. Malins. Amino Acid Sulfinate Salts as Alkyl Radical Precursors. Organic Letters 2023, 25 (17) , 3157-3162.
    12. Saurav Chatterjee, Anupam Bandyopadhyay. Cysteine-Selective Installation of Functionally Diverse Boronic Acid Probes on Peptides. Organic Letters 2023, 25 (13) , 2223-2227.
    13. Joomyung V. Jun, Yana D. Petri, Lucas W. Erickson, Ronald T. Raines. Modular Diazo Compound for the Bioreversible Late-Stage Modification of Proteins. Journal of the American Chemical Society 2023, 145 (12) , 6615-6621.
    14. Qinming Xu, Xing Li, Jingang Yang, Yan Zhang, Xiaocui Deng, Gang Li, Qingmei Yuan. Naphthyl-Poly(S-((2-carboxyethyl)thio)-l-cysteine) Peptide Amphiphiles with Different Degrees of Polymerization: Synthesis, Self-Assembly, pH/Reduction-Triggered Drug Release, and Cytotoxicity. Molecular Pharmaceutics 2023, 20 (2) , 1256-1268.
    15. Christopher W. Lamartina, Cassandra A. Chartier, Sumin Lee, Neel H. Shah, Tomislav Rovis. Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction. Journal of the American Chemical Society 2023, 145 (2) , 1129-1135.
    16. Yuyang Liu, Zeyuan He, Wen Ma, Guangjun Bao, Yiping Li, Changjun Yu, Jingyue Li, Ruiyao E, Zhaoqing Xu, Rui Wang, Wangsheng Sun. Copper(I)-Catalyzed Late-Stage Introduction of Oxime Ethers into Peptides at the Carboxylic Acid Site. Organic Letters 2022, 24 (50) , 9248-9253.
    17. Angel Gonzalez-Valero, Audrey G. Reeves, Annika C. S. Page, Patrick J. Moon, Edward Miller, Katia Coulonval, Steven W. M. Crossley, Xiao Xie, Dan He, Patricia Z. Musacchio, Alec H. Christian, Jeffrey M. McKenna, Richard A. Lewis, Eric Fang, Dustin Dovala, Yipin Lu, Lynn M. McGregor, Markus Schirle, John A. Tallarico, Pierre P. Roger, F. Dean Toste, Christopher J. Chang. An Activity-Based Oxaziridine Platform for Identifying and Developing Covalent Ligands for Functional Allosteric Methionine Sites: Redox-Dependent Inhibition of Cyclin-Dependent Kinase 4. Journal of the American Chemical Society 2022, 144 (50) , 22890-22901.
    18. Niki R. Patel Danielle Schultz . Leveraging HTE in Non-canonical Amino Acid Synthesis and Peptide Ligation. , 109-120.
    19. Alana M. M. Rangaswamy, Michael H. R. Beh, Ebrahim Soleimani, Steve Sequeira, Julie Cormier, Katherine N. Robertson, David L. Jakeman. Synthesis of 5′-Thymidine-Conjugated Formylphenylboronic Acids as Potential Lysine Targeting Iminoboronate Reversible Covalent Enzyme Probes. The Journal of Organic Chemistry 2022, 87 (21) , 13542-13555.
    20. Charlotte M. J. Wesseling, Nathaniel I. Martin. Synergy by Perturbing the Gram-Negative Outer Membrane: Opening the Door for Gram-Positive Specific Antibiotics. ACS Infectious Diseases 2022, 8 (9) , 1731-1757.
    21. Karsten A. S. Eastman, William M. Kincannon, Vahe Bandarian. Leveraging Substrate Promiscuity of a Radical S-Adenosyl-L-methionine RiPP Maturase toward Intramolecular Peptide Cross-Linking Applications. ACS Central Science 2022, 8 (8) , 1209-1217.
    22. Gang Li, Feipeng Yuan, Bo Yao. Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp3)–H Arylation. Organic Letters 2022, 24 (31) , 5767-5771.
    23. Marzieh Ahangarpour, Iman Kavianinia, Paul A. Hume, Paul W. R. Harris, Margaret A. Brimble. N-Vinyl Acrylamides: Versatile Heterobifunctional Electrophiles for Thiol–Thiol Bioconjugations. Journal of the American Chemical Society 2022, 144 (30) , 13652-13662.
    24. Daishiro Kobayashi, Eisuke Kuraoka, Junya Hayashi, Takuma Yasuda, Yutaka Kohmura, Masaya Denda, Norio Harada, Nobuya Inagaki, Akira Otaka. S-Protected Cysteine Sulfoxide-Enabled Tryptophan-Selective Modification with Application to Peptide Lipidation. ACS Medicinal Chemistry Letters 2022, 13 (7) , 1125-1130.
    25. Kosala N. Amarasinghe, Leonardo De Maria, Christian Tyrchan, Leif A. Eriksson, Jens Sadowski, Dušan Petrović. Virtual Screening Expands the Non-Natural Amino Acid Palette for Peptide Optimization. Journal of Chemical Information and Modeling 2022, 62 (12) , 2999-3007.
    26. Bo Li, Zhao Wan, Hanliang Zheng, Shaokun Cai, Han-Wen Tian, Hong Tang, Xin Chu, Gang He, Dong-Sheng Guo, Xiao-Song Xue, Gong Chen. Construction of Complex Macromulticyclic Peptides via Stitching with Formaldehyde and Guanidine. Journal of the American Chemical Society 2022, 144 (22) , 10080-10090.
    27. Jesper H. Mikkelsen, Magnus B. F. Gustafsson, Troels Skrydstrup, Kim B. Jensen. Selective N-Terminal Acylation of Peptides and Proteins with Tunable Phenol Esters. Bioconjugate Chemistry 2022, 33 (4) , 625-633.
    28. Natasha R. Cornejo, Bismark Amofah, Austin Lipinski, Paul R. Langlais, Indraneel Ghosh, John C. Jewett. Direct Intracellular Delivery of Benzene Diazonium Ions As Observed by Increased Tyrosine Phosphorylation. Biochemistry 2022, 61 (8) , 656-664.
    29. Maxwell O. Bowles, Caroline Proulx. Late-Stage N-Alkylation of Azapeptides. Organic Letters 2022, 24 (9) , 1768-1773.
    30. Shasha Li, Dmitri Pissarnitski, Timothy Nowak, Michael Wleklinski, Shane W. Krska. Merging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening. ACS Catalysis 2022, 12 (5) , 3201-3210.
    31. Titia Rixt Oppewal, Ivar D. Jansen, Johan Hekelaar, Clemens Mayer. A Strategy to Select Macrocyclic Peptides Featuring Asymmetric Molecular Scaffolds as Cyclization Units by Phage Display. Journal of the American Chemical Society 2022, 144 (8) , 3644-3652.
    32. Vivian M. Lechner, Manuel Nappi, Patrick J. Deneny, Sarah Folliet, John C. K. Chu, Matthew J. Gaunt. Visible-Light-Mediated Modification and Manipulation of Biomacromolecules. Chemical Reviews 2022, 122 (2) , 1752-1829.
    33. Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini, Casey B. Roos, Elizabeth A. McLoughlin, Benjamin G. Hejna, Suong T. Nguyen, Hunter H. Ripberger, Jacob M. Ganley, Elaine Tsui, Nick Y. Shin, Brian Koronkiewicz, Guanqi Qiu, Robert R. Knowles. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2017-2291.
    34. Kim B. Jensen, Jesper H. Mikkelsen, Simon P. Jensen, Steffen Kidal, Gitte Friberg, Troels Skrydstrup, Magnus B. F. Gustafsson. New Phenol Esters for Efficient pH-Controlled Amine Acylation of Peptides, Proteins, and Sepharose Beads in Aqueous Media. Bioconjugate Chemistry 2022, 33 (1) , 172-179.
    35. Angus S. Mackay, Richard J. Payne, Lara R. Malins. Electrochemistry for the Chemoselective Modification of Peptides and Proteins. Journal of the American Chemical Society 2022, 144 (1) , 23-41.
    36. Katsuya Maruyama, Takashi Ishiyama, Yohei Seki, Kentaro Sakai, Takaya Togo, Kounosuke Oisaki, Motomu Kanai. Protein Modification at Tyrosine with Iminoxyl Radicals. Journal of the American Chemical Society 2021, 143 (47) , 19844-19855.
    37. Qi-Long Hu, Jia-Tian Liu, Jian Li, Yang Ge, Zhendong Song, Albert S. C. Chan, Xiao-Feng Xiong. Demethylative Alkylation of Methionine Residue by Employing the Sulfonium as the Key Intermediate. Organic Letters 2021, 23 (21) , 8543-8548.
    38. Kyle W. Knouse, Dillon T. Flood, Julien C. Vantourout, Michael A. Schmidt, Ivar M. Mcdonald, Martin D. Eastgate, Phil S. Baran. Nature Chose Phosphates and Chemists Should Too: How Emerging P(V) Methods Can Augment Existing Strategies. ACS Central Science 2021, 7 (9) , 1473-1485.
    39. Lu Han, Qiang Shan. Different Behaviors of a Glycine Receptor Channel Pore Residue between Wild-Type-Mimicking and Disease-Type-Mimicking Formats. ACS Chemical Neuroscience 2021, 12 (18) , 3397-3409.
    40. Peijun Li, Jason R. Zbieg, Jack A. Terrett. A Platform for Decarboxylative Couplings via Photoredox Catalysis: Direct Access to Carbocations from Carboxylic Acids for Carbon–Oxygen Bond Formation. ACS Catalysis 2021, 11 (17) , 10997-11004.
    41. Yutong Lin, Lara R. Malins. An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes. Journal of the American Chemical Society 2021, 143 (30) , 11811-11819.
    42. José A. C. Delgado, José T. M. Correia, Emanuele F. Pissinati, Márcio W. Paixão. Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids. Organic Letters 2021, 23 (13) , 5251-5255.
    43. Ming Li, Sunday A. Akintelu, Bo Yao. Post-Assembly Modification of Peptides by Ligand-Enabled β-C(sp3)–H Arylation of Alanine at the C-Terminus: Overcoming the Inhibition Effect of Peptide Bonds. Organic Letters 2021, 23 (12) , 4807-4812.
    44. Zhuo Chen, Meijie Zhu, Mengwei Cai, Lulu Xu, Yiyi Weng. Palladium-Catalyzed C(sp3)–H Arylation and Alkynylation of Peptides Directed by Aspartic Acid (Asp). ACS Catalysis 2021, 11 (12) , 7401-7410.
    45. Bart I. Roman. The Expanding Role of Chemistry in Optimizing Proteins for Human Health Applications. Journal of Medicinal Chemistry 2021, 64 (11) , 7179-7188.
    46. Pengxin Wang, Yulian Cheng, Chunlei Wu, Yimin Zhou, Zhehong Cheng, Hongchang Li, Rui Wang, Wu Su, Lijing Fang. Tyrosine-Specific Modification via a Dearomatization–Rearomatization Strategy: Access to Azobenzene Functionalized Peptides. Organic Letters 2021, 23 (11) , 4137-4141.
    47. Fanyang Mo, Di Qiu, Lei Zhang, Jianbo Wang. Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds. Chemical Reviews 2021, 121 (10) , 5741-5829.
    48. Keita Nakane, Shinichi Sato, Tatsuya Niwa, Michihiko Tsushima, Shusuke Tomoshige, Hideki Taguchi, Minoru Ishikawa, Hiroyuki Nakamura. Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen. Journal of the American Chemical Society 2021, 143 (20) , 7726-7731.
    49. Napon Nilchan, James M. Alburger, William R. Roush, Christoph Rader. An Engineered Arginine Residue of Unusual pH-Sensitive Reactivity Facilitates Site-Selective Antibody Conjugation. Biochemistry 2021, 60 (14) , 1080-1087.
    50. Dacil Hernández, Carmen Carro, Alicia Boto. “Doubly Customizable” Unit for the Generation of Structural Diversity: From Pure Enantiomeric Amines to Peptide Derivatives. The Journal of Organic Chemistry 2021, 86 (3) , 2796-2809.
    51. Xiafei Hu, Xiangxiang Chen, Bo Li, Gang He, Gong Chen. Construction of Peptide Macrocycles via Radical-Mediated Intramolecular C–H Alkylations. Organic Letters 2021, 23 (3) , 716-721.
    52. Benjamin Laroche, Xinjun Tang, Gaétan Archer, Riccardo Di Sanza, Paolo Melchiorre. Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides. Organic Letters 2021, 23 (2) , 285-289.
    53. Peng Guo, Ke Wang, Wen-Jie Jin, Hao Xie, Liangliang Qi, Xue-Yuan Liu, Xing-Zhong Shu. Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis. Journal of the American Chemical Society 2021, 143 (1) , 513-523.
    54. Junyong Kim, Beryl X. Li, Richard Y.-C. Huang, Jennifer X. Qiao, William R. Ewing, David W. C. MacMillan. Site-Selective Functionalization of Methionine Residues via Photoredox Catalysis. Journal of the American Chemical Society 2020, 142 (51) , 21260-21266.
    55. Liu-Hai Wu, Shuguang Zhou, Qun-Feng Luo, Jie-Sheng Tian, Teck-Peng Loh. Dichloroacetophenone Derivatives: A Class of Bioconjugation Reagents for Disulfide Bridging. Organic Letters 2020, 22 (21) , 8193-8197.
    56. Zhen-Lin Hou, Feipeng Yuan, Bo Yao. Peptide Modification via N-Terminal-Residue-Directed γ-C(sp3)–H Arylation. Organic Letters 2020, 22 (21) , 8692-8696.
    57. Paula Andrade-Sampedro, Arkaitz Correa, Jon M. Matxain. On the Mechanism of Cross-Dehydrogenative Couplings between N-aryl Glycinates and Indoles: A Computational Study. The Journal of Organic Chemistry 2020, 85 (20) , 13133-13140.
    58. Julien C. Vantourout, Srinivasa Rao Adusumalli, Kyle W. Knouse, Dillon T. Flood, Antonio Ramirez, Natalia M. Padial, Alena Istrate, Katarzyna Maziarz, Justine N. deGruyter, Rohan R. Merchant, Jennifer X. Qiao, Michael A. Schmidt, Michael J. Deery, Martin D. Eastgate, Philip E. Dawson, Gonçalo J. L. Bernardes, Phil S. Baran. Serine-Selective Bioconjugation. Journal of the American Chemical Society 2020, 142 (41) , 17236-17242.
    59. Hyung-Joon Kang, Joon-Ho Lee, Dong-Hyun Kim, Cheon-Gyu Cho. Imidazole-Selective Alkyne Hydroamination under Physiological Conditions. Organic Letters 2020, 22 (19) , 7588-7593.
    60. Hongli Yin, Mengjie Zheng, Huan Chen, Siyao Wang, Qingqing Zhou, Qiang Zhang, Ping Wang. Stereoselective and Divergent Construction of β-Thiolated/Selenolated Amino Acids via Photoredox-Catalyzed Asymmetric Giese Reaction. Journal of the American Chemical Society 2020, 142 (33) , 14201-14209.
    61. Éric Godin, Jeffrey Santandrea, Antoine Caron, Shawn K. Collins. General Cu-Catalyzed Csp–S Coupling. Organic Letters 2020, 22 (15) , 5905-5909.
    62. Mark B. Richardson, Kristin N. Gabriel, Joseph A. Garcia, Shareen N. Ashby, Rebekah P. Dyer, Joshua K. Kim, Calvin J. Lau, John Hong, Ryan J. Le Tourneau, Sanjana Sen, David L. Narel, Benjamin B. Katz, Joseph W. Ziller, Sudipta Majumdar, Philip G. Collins, Gregory A. Weiss. Pyrocinchonimides Conjugate to Amine Groups on Proteins via Imide Transfer. Bioconjugate Chemistry 2020, 31 (5) , 1449-1462.
    63. Samantha J. Tower, Wesley J. Hetcher, Tyler E. Myers, Nicholas J. Kuehl, Michael T. Taylor. Selective Modification of Tryptophan Residues in Peptides and Proteins Using a Biomimetic Electron Transfer Process. Journal of the American Chemical Society 2020, 142 (20) , 9112-9118.
    64. Heemal H. Dhanjee, Azin Saebi, Ivan Buslov, Alexander R. Loftis, Stephen L. Buchwald, Bradley L. Pentelute. Protein–Protein Cross-Coupling via Palladium–Protein Oxidative Addition Complexes from Cysteine Residues. Journal of the American Chemical Society 2020, 142 (20) , 9124-9129.
    65. Alice L. Baumann, Sergej Schwagerus, Kevin Broi, Kristin Kemnitz-Hassanin, Christian E. Stieger, Nils Trieloff, Peter Schmieder, Christian P. R. Hackenberger. Chemically Induced Vinylphosphonothiolate Electrophiles for Thiol–Thiol Bioconjugations. Journal of the American Chemical Society 2020, 142 (20) , 9544-9552.
    66. Olivia Zhang, Jeffrey W. Schubert. Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition. The Journal of Organic Chemistry 2020, 85 (9) , 6225-6232.
    67. David Hymel, Fa Liu. Selective Lysine Modification Enabled by Intramolecular Acyl Transfer. Organic Letters 2020, 22 (8) , 3067-3071.
    68. Itziar Guerrero, Arkaitz Correa. Cu-Catalyzed Site-Selective C(sp2)–H Radical Trifluoromethylation of Tryptophan-Containing Peptides. Organic Letters 2020, 22 (5) , 1754-1759.
    69. Peng Ji, Yueteng Zhang, Yue Dong, He Huang, Yongyi Wei, Wei Wang. Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach. Organic Letters 2020, 22 (4) , 1557-1562.
    70. Mariafrancesca Scalise, Lara Console, Michele Galluccio, Lorena Pochini, Cesare Indiveri. Chemical Targeting of Membrane Transporters: Insights into Structure/Function Relationships. ACS Omega 2020, 5 (5) , 2069-2080.
    71. Hailey A. Young, Quibria A. E. Guthrie, Caroline Proulx. N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations. The Journal of Organic Chemistry 2020, 85 (3) , 1748-1755.
    72. Jia Zang, Yulin Chen, Wenxuan Zhu, Shixian Lin. Chemoselective Methionine Bioconjugation on a Polypeptide, Protein, and Proteome. Biochemistry 2020, 59 (2) , 132-138.
    73. Tyler J. Doyon, Jonathan C. Perkins, Summer A. Baker Dockrey, Evan O. Romero, Kevin C. Skinner, Paul M. Zimmerman, Alison R. H. Narayan. Chemoenzymatic o-Quinone Methide Formation. Journal of the American Chemical Society 2019, 141 (51) , 20269-20277.
    74. Feipeng Yuan, Zhen-Lin Hou, Pranab K. Pramanick, Bo Yao. Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation. Organic Letters 2019, 21 (23) , 9381-9385.
    75. Xiaoping Chen, Farong Ye, Xiaosheng Luo, Xueyi Liu, Jie Zhao, Siyao Wang, Qingqing Zhou, Gong Chen, Ping Wang. Histidine-Specific Peptide Modification via Visible-Light-Promoted C–H Alkylation. Journal of the American Chemical Society 2019, 141 (45) , 18230-18237.
    76. Mingcheng Yang, Tianpeng Cao, Tianxiao Xu, Saihu Liao. Visible-Light-Induced Deaminative Thioesterification of Amino Acid Derived Katritzky Salts via Electron Donor–Acceptor Complex Formation. Organic Letters 2019, 21 (21) , 8673-8678.
    77. Myles J. Terrey, Ashley Holmes, Carole C. Perry, Warren B. Cross. C–H Olefination of Tryptophan Residues in Peptides: Control of Residue Selectivity and Peptide–Amino Acid Cross-linking. Organic Letters 2019, 21 (19) , 7902-7907.
    78. Nozomu Inoue, Akira Onoda, Takashi Hayashi. Site-Specific Modification of Proteins through N-Terminal Azide Labeling and a Chelation-Assisted CuAAC Reaction. Bioconjugate Chemistry 2019, 30 (9) , 2427-2434.
    79. Thomas Schlatzer, Julia Kriegesmann, Hilmar Schröder, Melanie Trobe, Christian Lembacher-Fadum, Simone Santner, Alexander V. Kravchuk, Christian F. W. Becker, Rolf Breinbauer. Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine. Journal of the American Chemical Society 2019, 141 (37) , 14931-14937.
    80. Alec H. Christian, Shang Jia, Wendy Cao, Patricia Zhang, Arismel Tena Meza, Matthew S. Sigman, Christopher J. Chang, F. Dean Toste. A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation. Journal of the American Chemical Society 2019, 141 (32) , 12657-12662.
    81. Andrew J. Bendelsmith, Seohyun Chris Kim, Masayuki Wasa, Stéphane P. Roche, Eric N. Jacobsen. Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis. Journal of the American Chemical Society 2019, 141 (29) , 11414-11419.
    82. Amira H. Dardir, Nilay Hazari, Scott J. Miller, Christopher R. Shugrue. Palladium-Catalyzed Suzuki–Miyaura Reactions of Aspartic Acid Derived Phenyl Esters. Organic Letters 2019, 21 (14) , 5762-5766.
    83. Carlos J. Saavedra, Carmen Carro, Dácil Hernández, Alicia Boto. Conversion of “Customizable Units” into N-Alkyl Amino Acids and Generation of N-Alkyl Peptides. The Journal of Organic Chemistry 2019, 84 (13) , 8392-8410.
    84. Matthias Gehringer, Stefan A. Laufer. Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology. Journal of Medicinal Chemistry 2019, 62 (12) , 5673-5724.
    85. Bo Li, Xinghua Li, Boyang Han, Zhijie Chen, Xuekai Zhang, Gang He, Gong Chen. Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C–H Arylation. Journal of the American Chemical Society 2019, 141 (23) , 9401-9407.
    86. Michelle K. Quinn, Susan James, Jennifer J. McManus. Chemical Modification Alters Protein–Protein Interactions and Can Lead to Lower Protein Solubility. The Journal of Physical Chemistry B 2019, 123 (20) , 4373-4379.
    87. Mikael Madsen, Kurt V. Gothelf. Chemistries for DNA Nanotechnology. Chemical Reviews 2019, 119 (10) , 6384-6458.
    88. Yuanwei Dai, Jiaping Weng, Justin George, Huan Chen, Qishan Lin, Jun Wang, Maksim Royzen, Qiang Zhang. Three-Component Protein Modification Using Mercaptobenzaldehyde Derivatives. Organic Letters 2019, 21 (10) , 3828-3833.
    89. Shang Jia, Dan He, Christopher J. Chang. Bioinspired Thiophosphorodichloridate Reagents for Chemoselective Histidine Bioconjugation. Journal of the American Chemical Society 2019, 141 (18) , 7294-7301.
    90. Jameson R. Bothe, Alexandra Andrews, Katelyn J. Smith, Leo A. Joyce, Yogita Krishnamachari, Sandhya Kashi. Peptide Oligomerization Memory Effects and Their Impact on the Physical Stability of the GLP-1 Agonist Liraglutide. Molecular Pharmaceutics 2019, 16 (5) , 2153-2161.
    91. James S. Italia, Partha Sarathi Addy, Sarah B. Erickson, Jennifer C. Peeler, Eranthie Weerapana, Abhishek Chatterjee. Mutually Orthogonal Nonsense-Suppression Systems and Conjugation Chemistries for Precise Protein Labeling at up to Three Distinct Sites. Journal of the American Chemical Society 2019, 141 (15) , 6204-6212.
    92. Yu Kawamata, Julien C. Vantourout, David P. Hickey, Peng Bai, Longrui Chen, Qinglong Hou, Wenhua Qiao, Koushik Barman, Martin A. Edwards, Alberto F. Garrido-Castro, Justine N. deGruyter, Hugh Nakamura, Kyle Knouse, Chuanguang Qin, Khalyd J. Clay, Denghui Bao, Chao Li, Jeremy T. Starr, Carmen Garcia-Irizarry, Neal Sach, Henry S. White, Matthew Neurock, Shelley D. Minteer, Phil S. Baran. Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications. Journal of the American Chemical Society 2019, 141 (15) , 6392-6402.
    93. Bei-Bei Zhan, Jun Fan, Liang Jin, Bing-Feng Shi. Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly γ-C(sp3)–H Silylation. ACS Catalysis 2019, 9 (4) , 3298-3303.
    94. Lindsey C. Szymczak, Milan Mrksich. Using Peptide Arrays To Discover the Sequence-Specific Acetylation of the Histidine-Tyrosine Dyad. Biochemistry 2019, 58 (13) , 1810-1817.
    95. Zachary T. Ball. Protein Substrates for Reaction Discovery: Site-Selective Modification with Boronic Acid Reagents. Accounts of Chemical Research 2019, 52 (3) , 566-575.
    96. Yu Zhang, Yujie Liang, Feng Huang, Yue Zhang, Xuechen Li, Jiang Xia. Site-Selective Lysine Reactions Guided by Protein–Peptide Interaction. Biochemistry 2019, 58 (7) , 1010-1018.
    97. Myles J. Terrey, Carole C. Perry, Warren B. Cross. Postsynthetic Modification of Phenylalanine Containing Peptides by C–H Functionalization. Organic Letters 2019, 21 (1) , 104-108.
    98. Ting Cao, Jing Lv, Lei Zhang, Guoquan Yan, Haojie Lu. Selective Enrichment and Quantification of N-Terminal Glycine Peptides via Sortase A Mediated Ligation. Analytical Chemistry 2018, 90 (24) , 14303-14308.
    99. Shubo Du, Si Si Liew, Lin Li, Shao Q. Yao. Bypassing Endocytosis: Direct Cytosolic Delivery of Proteins. Journal of the American Chemical Society 2018, 140 (47) , 15986-15996.
    100. Jean B. Bertoldo, Hernán Terenzi, Stefan Hüttelmaier, Gonçalo J. L. Bernardes. Posttranslational Chemical Mutagenesis: To Reveal the Role of Noncatalytic Cysteine Residues in Pathogenic Bacterial Phosphatases. Biochemistry 2018, 57 (43) , 6144-6152.
    Load more citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect