Solid-Phase Synthesis of (ω-Aminoalkyl)peptoids Using Azide Chemistry

被引：8

作者：

Fritz, Daniel ^{[1
]}

Braese, Stefan ^{[1
]}

机构：

[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

来源：

SYNLETT | 2010年 / 10期

关键词：

peptoid; amines; azides; peptidomimetic transporters; solid-phase synthesis; microwave synthesis; protecting groups; CYCLOADDITION REACTIONS; DRUG-DELIVERY; PEPTOIDS; CELL; REDUCTION; EFFICIENT; CONSTRUCTION; CONJUGATION; OLIGOMERS; PEPTIDES;

D O I：

10.1055/s-0029-1219925

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized (omega-aminoalkyl)peptoids - useful molecular transporters for drugs and probes into cells - have been synthesized by a combined microwave-assisted sub-monomer peptoid synthesis with 1-amino-omega-azidoalkanes and a subsequent reduction of the azide moiety on solid supports. This method enables the preparation of unprecedented chiral amino-functionalized and PEG-type peptoids. Both the scope and limitations of this process are presented herein.

引用

页码：1544 / 1548

页数：5

共 37 条

[1] Efficient fluorescein spirolactam and bis-spirolactam synthesis [J].

Adamczyk, M ;

Grote, J .

SYNTHETIC COMMUNICATIONS, 2001, 31 (17) :2681-2690

[2]

BARRON AE, 2000, Patent No. 2000043547

[3] NEW SYNTHETIC TRICKS - [ET3NH][SN(SPH)3] AND BU2SNH2, 2 USEFUL REAGENTS FOR THE REDUCTION OF AZIDES TO AMINES [J].

BARTRA, M ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1987, 28 (47) :5941-5944

[4] A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].

BARTRA, M ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON, 1990, 46 (02) :587-594

[5] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[6]

Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657

[7] Peptoid dendrimers-microwave-assisted solid-phase synthesis and transfection agent evaluation [J].

Diaz-Mochon, Juan J. ;

Fara, Mario A. ;

Sanchez-Martin, Rosario M. ;

Bradley, Mark .

TETRAHEDRON LETTERS, 2008, 49 (05) :923-926

[8]

DISNEY MD, 2008, Patent No. 20081034898

[9] Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides -: a gentle heat goes a long way [J].

Fara, MA ;

Díaz-Mochón, JJ ;

Bradley, M .

TETRAHEDRON LETTERS, 2006, 47 (06) :1011-1014

[10] Synthesis of a coumarin-based europium complex for bioanalyte labeling [J].

Feau, Clementine ;

Klein, Emmanuel ;

Kerth, Paul ;

Lebeau, Luc .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (06) :1499-1503

← 1 2 3 4 →