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

页码：6225 / 6232

页数：8

共 50 条

[21] Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane
Szakonyi, Zsolt
Balazs, Arpad
Martinek, Tamas A.
Fulop, Ferenc
TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2498 - 2504
[22] Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine
Li, Guo-Xing
Morales-Rivera, Christian A.
Wang, Yaxin
Gao, Fang
He, Gang
Liu, Peng
Chen, Gong
CHEMICAL SCIENCE, 2016, 7 (10) : 6407 - 6412
[23] HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: synthesis and stereochemical analysis of β-benzotriazole N-oxide substituted γ-amino acids and hybrid peptides
Mali, Sachitanand M.
Kumar, Mothukuri Ganesh
Katariya, Mona M.
Gopi, Hosahudya N.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (42) : 8462 - 8472
[24] Intermolecular Conjugate Addition of Pyrroloindoline and Furoindoline Radicals to α,β-Unsaturated Enones via Photoredox Catalysis
Zhou, Shupeng
Zhang, Deliang
Sun, Yu
Li, Ruofan
Zhang, Wenhao
Li, Ang
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2867 - 2872
[25] Solid phase derivatization of amino acids and peptides on alkaline silica gel support
Shangguan, DH
Zhao, YX
Han, HW
Zhao, R
Liu, GQ
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2002, 23 (03): : 385 - 387
[26] Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis
Reyes, Avelyn Mae V. Delos
Escobar, Christopher S. Nieves
Munoz, Alberto
Huffman, Maya I.
Tan, Derek S.
CHEMICAL SCIENCE, 2023, 14 (38) : 10524 - 10531
[27] Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Scherbinina, Sofya I.
Fedorov, Oleg V.
Levin, Vitalij V.
Kokorekin, Vladimir A.
Struchkova, Marina I.
Dilman, Alexander D.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 12967 - 12974
[28] DNA-encoded C-H functionality via photoredox-mediated hydrogen atom transformation catalysis
Shan, Jinming
Ling, Xing
Liu, JiaXiang
Wang, Xuan
Lu, Xiaojie
BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 42
[29] PHOTOCHEMICAL ADDITION OF AMINO-ACIDS AND PEPTIDES TO POLYURYDYLIC ACID
SHETLAR, MD
CARBONE, J
STEADY, E
HOM, K
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 186 (AUG): : 170 - BIOL
[30] PHOTOCHEMICAL ADDITION OF AMINO-ACIDS AND PEPTIDES TO POLYURIDYLIC ACID
SHETLAR, MD
CARBONE, J
STEADY, E
HOM, K
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1984, 39 (02) : 141 - 144

← 1 2 3 4 5 →