Chemoselective Pd(0)-catalyzed peptide coupling in water

被引：74

作者：

Bong, DT

Ghadiri, MR

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 16期

关键词：

D O I：

10.1021/ol016169e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly charged peptides ranging In length from 17 to 33 residues have been efficiently tricoupled to a trialkyne nucleus by using a Sonogashira Pd(0) coupling strategy under both acidic (pH 5.0) and basic (pH 7.5) conditions. These results demonstrate the utility of Pd(0) to construct protein-sized structures (12,000 mol wt) in aqueous milieu.

引用

页码：2509 / 2511

页数：3

共 25 条

[1] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
AMATORE, C
BLART, E
GENET, JP
JUTAND, A
LEMAIREAUDOIRE, S
SAVIGNAC, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
[2] PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA
CASALNUOVO, AL
CALABRESE, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4324 - 4330
[3] Enantiomerically pure pyridine and 2,2′-bipyridine thioethers:: new N-S chiral ligands for asymmetric catalysis.: Palladium-catalyzed allylic alkylation
Chelucci, G
Culeddu, N
Saba, A
Valenti, R
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (18) : 3537 - 3546
[4] Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalysed allylic substitution
Chesney, A
Bryce, MR
Chubb, RWJ
Batsanov, AS
Howard, JAK
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (14) : 2337 - 2346
[5] Dibowski H, 1998, ANGEW CHEM INT EDIT, V37, P476, DOI 10.1002/(SICI)1521-3773(19980302)37:4<476::AID-ANIE476>3.0.CO
[6] 2-2
[7] GENET JP, 1992, SYNLETT, P715
[8] SUZUKI-TYPE CROSS-COUPLING REACTIONS USING PALLADIUM-WATER SOLUBLE CATALYST - SYNTHESIS OF FUNCTIONALIZED DIENES
GENET, JP
LINQUIST, A
BLART, E
MOURIES, V
SAVIGNAC, M
VAULTIER, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (09) : 1443 - 1446
[9] PEPTIDE ARCHITECTURE - DESIGN OF STABLE ALPHA-HELICAL METALLOPEPTIDES VIA A NOVEL EXCHANGE-INERT RUIII COMPLEX
GHADIRI, MR
FERNHOLZ, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) : 9633 - 9635
[10] SECONDARY STRUCTURE NUCLEATION IN PEPTIDES - TRANSITION-METAL ION STABILIZED ALPHA-HELICES
GHADIRI, MR
CHOI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) : 1630 - 1632

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