Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition

被引：40
|
作者：
Zhang, Olivia [1 ]
Schubert, Jeffrey W. [1 ]
机构：
[1] Merck & Co Inc, Dept Discovery Chem, West Point, PA 19486 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 09期
关键词：
DERIVATIVES; ROUTE;
D O I：
10.1021/acs.joc.0c00635
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide.
引用
收藏
页码：6225 / 6232
页数：8
相关论文
共 50 条
  • [41] Synthesis of conformationally constrained hydroxy-α-amino acids by intramolecular conjugate addition
    A. Avenoza
    J. H. Busto
    C. Cativiela
    J. M. Peregrina
    Amino Acids, 2000, 18 : 117 - 127
  • [42] Synthesis of conformationally constrained hydroxy-α-amino acids by intramolecular conjugate addition
    Avenoza, A
    Busto, JH
    Cativiela, C
    Peregrina, JM
    AMINO ACIDS, 2000, 18 (02) : 117 - 127
  • [43] Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis
    Chippindale, AM
    Davies, SG
    Iwamoto, K
    Parkin, RM
    Smethurst, CAP
    Smith, AD
    Rodriguez-Solla, H
    TETRAHEDRON, 2003, 59 (18) : 3253 - 3265
  • [44] Chiral amino alcohol-mediated asymmetric conjugate addition of arylalkynes to nitroolefins
    Yamashita, M
    Yamada, K
    Tomioka, K
    ORGANIC LETTERS, 2005, 7 (12) : 2369 - 2371
  • [45] Derivatization of amino acids, peptides and proteins for laser-induced fluorescence detection in capillary electrophoresis
    Ryvolová, M
    Táborsky, P
    Vrábel, P
    Havel, J
    Preisler, J
    CHEMICKE LISTY, 2006, 100 (03): : 191 - 195
  • [46] Metal-Catalyzed Derivatization of Cα-Tetrasubstituted Amino Acids and Their Use in the Synthesis of Cyclic Peptides
    Grauer, Andreas
    Spaeth, Andreas
    Ma, Dawei
    Koenig, Burkhard
    CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) : 1134 - 1140
  • [47] On-column derivatization and analysis of amino acids, peptides, and alkylamines by anhydrides using capillary electrophoresis
    Zhang, Y
    Gomez, FA
    ELECTROPHORESIS, 2000, 21 (15) : 3305 - 3310
  • [48] Visible-Light-Curable Solvent-Free Acrylic Pressure-Sensitive Adhesives via Photoredox-Mediated Radical Polymerization
    Back, Jong-Ho
    Kwon, Yonghwan
    Kim, Hyun-Joong
    Yu, Youngchang
    Lee, Wonjoo
    Kwon, Min Sang
    MOLECULES, 2021, 26 (02):
  • [49] Enzymatic N-terminal addition of noncanonical amino acids to peptides and proteins
    Connor, Rebecca E.
    Piatkov, Konstantin
    Varshavsky, Alexander
    Tirrell, David A.
    CHEMBIOCHEM, 2008, 9 (03) : 366 - 369
  • [50] Access to Deuterated Unnatural α-Amino Acids and Peptides by Photochemical Acyl Radical Addition
    Liu, Li
    Deng, Zikun
    Xu, Kun
    Jiang, Pengxing
    Du, Hongguang
    Tan, Jiajing
    ORGANIC LETTERS, 2021, 23 (14) : 5299 - 5304
12345