Internal labeling of oligonucleotide probes by Diels-Alder cycloaddition

被引：36

作者：

Graham, D ^{[1
]}

Grondin, A ^{[1
]}

McHugh, C ^{[1
]}

Fruk, L ^{[1
]}

Smith, WE ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 27期

基金：

英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(02)00930-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method of adding fluorescent labels to the middle of oligonucleotides is reported. Diets-Alder cycloaddition was used to add five fluorescent maleimides to an oligonucleotide containing a 2'-deoxyuridine modified at the 5-position with a spaced furan. This is a new approach to internal oligonucleotide chemistry that opens Lip a large range of possibilities for further conjugation. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4785 / 4788

页数：4

共 8 条

[1] Antisense inhibition of P-glycoprotein expression using peptide-oligonucleotide conjugates [J].

Astriab-Fisher, A ;

Sergueev, DS ;

Fisher, M ;

Shaw, BR ;

Juliano, RL .

BIOCHEMICAL PHARMACOLOGY, 2000, 60 (01) :83-90

[2] Synthesis of a modified thymidine monomer for site-specific incorporation of reporter groups into oligonucleotides [J].

Brown, LJ ;

May, JP ;

Brown, T .

TETRAHEDRON LETTERS, 2001, 42 (13) :2587-2591

[3]

Christopoulos TK, 1999, ANAL CHEM, V71, p425R

[4] Synthesis of fluorescently labelled oligonucleotides and nucleic acids [J].

Davies, MJ ;

Shah, A ;

Bruce, IJ .

CHEMICAL SOCIETY REVIEWS, 2000, 29 (02) :97-107

[5] Benzotriazole maleimide as a bifunctional reactant for SERS [J].

Grondin, A ;

Robson, DC ;

Smith, WE ;

Graham, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (11) :2136-2141

[6] Diels-Alder bioconjugation of diene-modified oligonucleotides [J].

Hill, KW ;

Taunton-Rigby, J ;

Carter, JD ;

Kropp, E ;

Vagle, K ;

Pieken, W ;

McGee, DPC ;

Husar, GM ;

Leuck, M ;

Anziano, DJ ;

Sebesta, DP .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5352-5358

[7] Stability, specificity and fluorescence brightness of multiply-labeled fluorescent DNA probes [J].

Randolph, JB ;

Waggoner, AS .

NUCLEIC ACIDS RESEARCH, 1997, 25 (14) :2923-2929

[8]

Wojczewski C, 1999, SYNLETT, P1667

← 1 →