Internal Peptide Late-Stage Diversification: Peptide-Isosteric Triazoles for Primary and Secondary C(sp3)-H Activation

被引：117

作者：

Bauer, Michaela ^{[1
]}

Wang, Wei ^{[1
]}

Lorion, Melanie M. ^{[1
]}

Dong, Chuan ^{[1
]}

Ackermann, Lutz ^{[1
]}

机构：

[1] Georg August Univ, Inst Organ & Biomol Chem, Tammanstr 2, D-37077 Gottingen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 01期

关键词：

amino acids; arylation; palladium; peptides; triazoles; C-H ACTIVATION; ALPHA-AMINO-ACIDS; CARBON-HYDROGEN BONDS; DIRECTING GROUP; UNACTIVATED C(SP(3))-H; COUPLING REACTIONS; DIRECT ARYLATIONS; PALLADIUM; FUNCTIONALIZATION; PEPTIDOMIMETICS;

D O I：

10.1002/anie.201710136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Secondary C(sp(3))-H arylations were accomplished by palladium catalysis with triazoles as peptide bond isosteres. The unique power of this approach is highlighted by the possibility of achieving secondary C(sp(3))-H functionalizations on terminal peptides as well as the unprecedented positional-selective C(sp(3))-H functionalization of internal peptide positions, setting the stage for modular peptide late-stage diversification.

引用

页码：203 / 207

页数：5

共 104 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[3] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[4] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus [J].

Ackermann, Lutz ;

Potukuchi, Harish Kumar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4503-4513

[5] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[6] Ruthenium-Catalyzed Direct Arylations of N-Aryl 1,2,3-Triazoles with Aryl Chlorides as Electrophiles [J].

Ackermann, Lutz ;

Born, Robert ;

Vicente, Ruben .

CHEMSUSCHEM, 2009, 2 (06) :546-549

[7] Regio- and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)-H Arylation [J].

Affron, Dominic P. ;

Davis, Owen A. ;

Bull, James A. .

ORGANIC LETTERS, 2014, 16 (18) :4956-4959

[8] Hydantoinases and related enzymes as biocatalysts for the synthesis of unnatural chiral amino acids [J].

Altenbuchner, J ;

Siemann-Herzberg, M ;

Syldatk, C .

CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (06) :559-563

[9] Functionalized triazolopeptoids - a novel class for mitochondrial targeted delivery [J].

Althuon, Daniela ;

Roenicke, Franziska ;

Fuerniss, Daniel ;

Quan, Jasmin ;

Wellhoefer, Isabelle ;

Jung, Nicole ;

Schepers, Ute ;

Braese, Stefan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) :4226-4230

[10] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].

Angell, Yu L. ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689

← 1 2 3 4 5 6 7 8 9 10 →