Biaryl Peptides from 4-Iodophenylalanine by Solid-Phase Borylation and Suzuki-Miyaura Cross-Coupling

被引：21

作者：

Afonso, Ana ^{[1
]}

Roses, Cristina ^{[1
]}

Planas, Marta ^{[1
]}

Feliu, Lidia ^{[1
]}

机构：

[1] Univ Girona, LIPPSO, Dept Quim, Girona 17071, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 08期

关键词：

Borylation; Biaryl peptides; Microwave chemistry; Cross-coupling; Solid-phase synthesis; BORONIC ACID; AMINO-ACIDS; PHENYLALANINE; ANALOGS;

D O I：

10.1002/ejoc.200901350

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Resin-bound phenylalanine boronates were prepared by solid-phase Miyaura borylation of 4-iodophenylalanine peptides. Subsequent arylation through a Suzuki-Miyaura cross-coupling was carried out using a variety of aryl halides under conventional heating and under microwave irradiation. Microwaves greatly enhanced the arylation, shortening the reaction time and providing the biaryl peptides in higher purities.

引用

收藏

页码：1461 / 1468

页数：8

相关论文

共 28 条

[1] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].

Alonso, Francisco ;

Beletskaya, Irina P. ;

Yus, Miguel .

TETRAHEDRON, 2008, 64 (14) :3047-3101

[2] Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines [J].

Capek, Petr ;

Pohl, Radek ;

Hocek, Michal .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2278-2284

[3]

Cepanec I., 2004, Synthesis of Biaryls

[4] Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling [J].

Cerezo, Vanessa ;

Amblard, Muriel ;

Martinez, Jean ;

Verdie, Pascal ;

Planas, Marta ;

Feliu, Lidia .

TETRAHEDRON, 2008, 64 (46) :10538-10545

[5] Effectiveness of the Suzuki-Miyaura cross-coupling reaction for solid-phase peptide modification [J].

Doan, Ngoc-Duc ;

Bourgault, Steve ;

Letourneau, Myriam ;

Fournier, Alain .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (01) :44-51

[6] The preparation of solid-supported peptide boronic acids derived from 4-borono-L-phenylalanine and their affinity for alizarin [J].

Duggan, Peter J. ;

Offermann, Daniel A. .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (11) :829-834

[7] Application of fast reversed phase liquid chromatography for analysis of pharmaceutical related boronic acid and boronic pinacol ester functionalized compounds [J].

Duran, D ;

Wu, N ;

Mao, B ;

Xu, J .

JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2006, 29 (05) :661-672

[8] Cyclic peptides containing biaryl and biaryl ether linkages [J].

Feliu, L ;

Planas, M .

INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2005, 11 (01) :53-97

[9] Enantioselective synthesis of 4-substituted phenylalanines by cross-coupling reactions [J].

Firooznia, F ;

Gude, C ;

Chan, K ;

Marcopulos, N ;

Satoh, Y .

TETRAHEDRON LETTERS, 1999, 40 (02) :213-216

[10] Synthesis and biological evaluation of novel pyridazinone-based α4 integrin receptor antagonists [J].

Gong, Yong ;

Barbay, J. Kent ;

Dyatkin, Alexey B. ;

Miskowski, Tamara A. ;

Kimball, Edward S. ;

Prouty, Stephen M. ;

Fisher, M. Carolyn ;

Santulli, Rosemary J. ;

Schneider, Craig R. ;

Wallace, Nathaniel H. ;

Ballentine, Scott A. ;

Hageman, William E. ;

Masucci, John A. ;

Maryanoff, Bruce E. ;

Damiano, Bruce P. ;

Andrade-Gordon, Patricia ;

Hlasta, Dennis J. ;

Hornby, Pamela J. ;

He, Wei .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (11) :3402-3411