Synthesis of new molecules containing head, spacer, and label moieties

被引:24
作者
Khatyr, A [1 ]
Maas, H [1 ]
Calzaferri, G [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
D O I
10.1021/jo025691r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the synthesis and characterization of novel molecules containing head with precise shape, spacer, and label moieties. The protocol is based on a Pd(0)-catalyzed cross-coupling reaction between ethynylphenyl/bromide to obtain a rigid head followed by the attachment of a flexible spacer possessing two reactive functional groups on the termini. The final step consists of forming a covalent bond between spacer and label. In addition, monosubstituted soluble labels were synthesized in good yields.
引用
收藏
页码:6705 / 6710
页数:6
相关论文
共 31 条
[1]   Novel building blocks for biomimetic assemblies. Synthesis, characterization, and spectroscopic and electrochemical properties of new bidentate ligands derived from lysine and cysteine and their complexes with bis(2,2'-bipyridine)ruthenium(II) [J].
Alsfasser, R ;
vanEldik, R .
INORGANIC CHEMISTRY, 1996, 35 (03) :628-636
[2]   Photonic antenna system for light harvesting, transport and trapping [J].
Calzaferri, G ;
Pauchard, M ;
Maas, H ;
Huber, S ;
Khatyr, A ;
Schaafsma, T .
JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (01) :1-13
[3]   Playing with dye molecules at the inner and outer surface of zeolite L [J].
Calzaferri, G ;
Brühwiler, D ;
Megelski, S ;
Pfenniger, M ;
Pauchard, M ;
Hennessy, B ;
Maas, H ;
Devaux, A ;
Graf, U .
SOLID STATE SCIENCES, 2000, 2 (04) :421-447
[5]   Preparation of stilbene-tethered nonnatural nucleosides for use with blue-fluorescent antibodies [J].
Chen, DW ;
Beuscher, AE ;
Stevens, RC ;
Wirsching, P ;
Lerner, RA ;
Janda, KD .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1725-1732
[6]   Palladium-catalysed attachment of labels with acetylenic linker arms to biological molecules [J].
Crisp, GT ;
Gore, J .
TETRAHEDRON, 1997, 53 (04) :1523-1544
[7]  
DEVI YU, 1990, INDIAN J CHEM B, V29, P898
[8]   LONG-RANGE MOLECULAR ORDER AS AN EFFICIENT STRATEGY FOR LIGHT HARVESTING IN PHOTOSYNTHESIS [J].
FETISOVA, ZG ;
FREIBERG, AM ;
TIMPMANN, KE .
NATURE, 1988, 334 (6183) :633-634
[9]  
Geisser B, 1998, EUR J INORG CHEM, P957
[10]   A new protecting group for aspartic acid that minimizes piperidine-catalyzed aspartimide formation in Fmoc solid phase peptide synthesis [J].
Karlstrom, A ;
Unden, A .
TETRAHEDRON LETTERS, 1996, 37 (24) :4243-4246