A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds

被引:527
作者
Saxon, E
Armstrong, JI
Bertozzi, CR [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ol006054v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine, This method for the selective formation of an amide bond, which does not require the orthogonal protection of distal functional groups, should find general utility in synthetic and biological chemistry.
引用
收藏
页码:2141 / 2143
页数:3
相关论文
共 17 条
[1]   AN EASILY INTRODUCED AND REMOVED PROTECTING GROUP FOR IMIDAZOLE NITROGEN - A CONVENIENT ROUTE TO 2-SUBSTITUTED IMIDAZOLES [J].
CURTIS, NJ ;
BROWN, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :4038-4040
[2]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[3]   DIRECTED ORTHO-LITHIATION OF LITHIUM THIOPHENOLATE - NEW METHODOLOGY FOR THE PREPARATION OF ORTHO-SUBSTITUTED THIOPHENOLS AND RELATED-COMPOUNDS [J].
FIGULY, GD ;
LOOP, CK ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :654-658
[4]   Palladium catalyzed P-C coupling - a powerful tool for the syntheses of hydrophilic phosphines [J].
Herd, O ;
Hessler, A ;
Hingst, M ;
Machnitzki, P ;
Tepper, M ;
Stelzer, O .
CATALYSIS TODAY, 1998, 42 (04) :413-420
[5]   Chemoselective ligation reactions with proteins, oligosaccharides and cells [J].
Lemieux, GA ;
Bertozzi, CR .
TRENDS IN BIOTECHNOLOGY, 1998, 16 (12) :506-513
[6]   PHOSPHORAMIDATE ANALOGS OF DINUCLEOTIDES - SYNTHESIS AND H-1 ASSIGNMENT BY TWO-DIMENSIONAL NMR-SPECTROSCOPY (H-1,H-1-COSY) [J].
MAG, M ;
ENGELS, JW .
NUCLEOSIDES & NUCLEOTIDES, 1988, 7 (5-6) :725-728
[7]   Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis [J].
Mahal, LK ;
Yarema, KJ ;
Bertozzi, CR .
SCIENCE, 1997, 276 (5315) :1125-1128
[8]   Combinatorial target-guided ligand assembly: Identification of potent subtype-selective c-Src inhibitors [J].
Maly, DJ ;
Choong, IC ;
Ellman, JA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (06) :2419-2424
[9]   Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides [J].
Mizuno, M ;
Haneda, K ;
Iguchi, R ;
Muramoto, I ;
Kawakami, T ;
Aimoto, S ;
Yamamoto, K ;
Inazu, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :284-290
[10]   Expressed protein ligation: A general method for protein engineering [J].
Muir, TW ;
Sondhi, D ;
Cole, PA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (12) :6705-6710