Efficient Synthesis of 5-Hydroxymethylcytosine Containing DNA

被引：37

作者：

Muenzel, Martin ^{[1
]}

Globisch, Daniel ^{[1
]}

Trindler, Christian ^{[1
]}

Carell, Thomas ^{[1
]}

机构：

[1] Univ Munich, Ctr Integrated Prot Sci, Dept Chem, D-81377 Munich, Germany

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 24期

关键词：

5-METHYLCYTOSINE; QUANTIFICATION; CONVERSION; CHEMISTRY; ANALOGS; BRAIN;

D O I：

10.1021/ol102408t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Hydroxymethylcytosine ((5-HOMe)dC) was recently discovered as the sixth base in the mammalian genome. The development of a new phosphoramidite building block is reported, which allows efficient synthesis of (5-HOMe)dC containing DNA. Key steps of the synthesis are a palladium-catalyzed formylation and the simultaneous protection of a hydroxyl and amino group as a cyclic carbamate. DNA synthesis is possible under standard conditions, and deprotection can be carried out with dilute NaOH.

引用

页码：5671 / 5673

页数：3

共 16 条

[1] CHEMICAL SYNTHESIS OF DNA AND DNA ANALOGS [J].

CARUTHERS, MH .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (09) :278-284

[2] Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA [J].

Gierlich, Johannes ;

Burley, Glenn A. ;

Gramlich, Philipp M. E. ;

Hammond, David M. ;

Carell, Thomas .

ORGANIC LETTERS, 2006, 8 (17) :3639-3642

[3] Postsynthetic DNA Modification through the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction [J].

Gramlich, Philipp M. E. ;

Wirges, Christian T. ;

Manetto, Antonio ;

Carell, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8350-8358

[4]

Hwang C.H., 1992, Arch. Pharmacal Res, V15, P69, DOI [DOI 10.1007/BF02973987, 10.1007/BF02973987]

[5] Role of Tet proteins in 5mC to 5hmC conversion, ES-cell self-renewal and inner cell mass specification [J].

Ito, Shinsuke ;

D'Alessio, Ana C. ;

Taranova, Olena V. ;

Hong, Kwonho ;

Sowers, Lawrence C. ;

Zhang, Yi .

NATURE, 2010, 466 (7310) :1129-U151

[6] The Nuclear DNA Base 5-Hydroxymethylcytosine Is Present in Purkinje Neurons and the Brain [J].

Kriaucionis, Skirmantas ;

Heintz, Nathaniel .

SCIENCE, 2009, 324 (5929) :929-930

[7] Establishing, maintaining and modifying DNA methylation patterns in plants and animals [J].

Law, Julie A. ;

Jacobsen, Steven E. .

NATURE REVIEWS GENETICS, 2010, 11 (03) :204-220

[8] Oxygenase Catalyzed 5-Methylcytosine Hydroxylation [J].

Loenarz, Christoph ;

Schofield, Christopher J. .

CHEMISTRY & BIOLOGY, 2009, 16 (06) :580-583

[9] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES [J].

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) :2226-2227

[10] Synthesis and properties of a new fluorescent bicyclic 4-N-carbamoyldeoxycytidine derivative [J].

Miyata, K ;

Tamamushi, R ;

Ohkubo, A ;

Taguchi, H ;

Seio, K ;

Santa, T ;

Sekine, M .

ORGANIC LETTERS, 2006, 8 (08) :1545-1548

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