Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry

被引：10
作者：
Bao, Yandan [1 ,2 ]
Xing, Minyan [3 ]
Matthew, Naylor [4 ]
Chen, Xiaohua [2 ,5 ]
Wang, Xuan [2 ]
Lu, Xiaojie [1 ,2 ,5 ]
机构：
[1] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Zhang Jiang Hitech Pk, Shanghai 201203, Peoples R China
[3] China Pharmaceut Univ, Sch Pharm, Nanjing 211198, Peoples R China
[4] UCB, Cambridge, MA 02140 USA
[5] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 26卷 / 14期
关键词：
IN-VITRO; LIBRARIES; SELECTION; PROTEINS; DESIGN;
D O I：
10.1021/acs.orglett.3c01817
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
While DNA-encoded macrocyclic libraries have gained substantialattention and several hit compounds have been identified from DNA-encodedlibrary technology, efficient on-DNA macrocyclic methods are alsorequired to construct DNA-linked libraries with a high degree of cyclizationand DNA integrity. In this paper, we reported a set of on-DNA methodologies,including the use of an OPA-mediated three-component cyclization withnative handles of amino acids and photoredox chemistries. These chemistriesproceed smoothly under mild conditions in good to excellent conversions,successfully generating novel isoindole, isoindoline, indazolone,and bicyclic scaffolds.
引用
收藏
页码：2763 / 2767
页数：5
相关论文
共 29 条
  • [1] Construction and screening of vast libraries of natural product-like macrocyclic peptides using in vitro display technologies
    Bashiruddin, Nasir K.
    Suga, Hiroaki
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2015, 24 : 131 - 138
  • [2] Macrocyclization strategies for cyclic peptides and peptidomimetics
    Bechtler, Clement
    Lamers, Christina
    [J]. RSC MEDICINAL CHEMISTRY, 2021, 12 (08): : 1325 - 1351
  • [3] Synthesis of a DNA-Encoded Macrocyclic Library Utilizing Intramolecular Benzimidazole Formation
    Chai, Jing
    Arico-Muendel, Christopher C.
    Ding, Yun
    Pollastri, Michael P.
    Scott, Sarah
    Mantell, Mark A.
    Yao, Gang
    [J]. BIOCONJUGATE CHEMISTRY, 2023, 34 (06) : 988 - 993
  • [4] Bioconjugation via Hetero-Selective Clamping of Two Different Amines with ortho-Phthalaldehyde
    Chu, Xin
    Li, Bo
    Liu, Hao-Yang
    Sun, Xiaowei
    Yang, Xiaochen
    He, Gang
    Zhou, Chuanzheng
    Xuan, Weimin
    Liu, Shu-Lin
    Chen, Gong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)
  • [5] DNA-templated organic synthesis and selection of a library of macrocycles
    Gartner, ZJ
    Tse, BN
    Grubina, R
    Doyon, JB
    Snyder, TM
    Liu, DR
    [J]. SCIENCE, 2004, 305 (5690) : 1601 - 1605
  • [6] Light-induced efficient and residue-selective bioconjugation of native proteins via indazolone formation
    Guo, An-Di
    Wu, Ke-Huan
    Chen, Xiao-Hua
    [J]. RSC ADVANCES, 2021, 11 (04) : 2235 - 2241
  • [7] Light-induced primary amines and o-nitrobenzyl alcohols cyclization as a versatile photoclick reaction for modular conjugation
    Guo, An-Di
    Wei, Dan
    Nie, Hui-Jun
    Hu, Hao
    Peng, Chengyuan
    Li, Shao-Tong
    Yan, Ke-Nian
    Zhou, Bin-Shan
    Feng, Lei
    Fang, Chao
    Tan, Minjia
    Huang, Ruimin
    Chen, Xiao-Hua
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)
  • [8] 2-Nitroveratryl as a Photocleavable Thiol-Protecting Group for Directed Disulfide Bond Formation in the Chemical Synthesis of Insulin
    Karas, John A.
    Scanlon, Denis B.
    Forbes, Briony E.
    Vetter, Irina
    Lewis, Richard J.
    Gardiner, James
    Separovic, Frances
    Wade, John D.
    Hossain, Mohammed A.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (31) : 9549 - 9552
  • [9] Structure-based drug design of a highly potent CDK1,2,4,6 inhibitor with novel macrocyclic quinoxalin-2-one structure
    Kawanishi, Nobuhiko
    Sugimoto, Tetsuya
    Shibata, Jun
    Nakamura, Kaori
    Masutani, Kouta
    Ikuta, Marl
    Hirai, Hiroshi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) : 5122 - 5126
  • [10] Davis-Beirut Reaction: A Photochemical Bronsted Acid Catalyzed Route to N-Aryl 2H-Indazoles
    Kraemer, Niklas
    Li, Clarabella J.
    Zhu, Jie S.
    Larach, Julio M.
    Tsui, Ka Yi
    Tantillo, Dean J.
    Haddadin, Makhluf J.
    Kurth, Mark J.
    [J]. ORGANIC LETTERS, 2019, 21 (15) : 6058 - 6062
123