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Syntheses of Two 5-Hydroxymethyl-2'-deoxycytidine Phosphoramidites with TBDMS as the 5-Hydroxymethyl Protecting Group and Their Incorporation into DNA.
- Source :
-
Journal of Organic Chemistry . 5/20/2011, Vol. 76 Issue 10, p4182-4188. 7p. - Publication Year :
- 2011
-
Abstract
- 5-Hydroxymethylcytosine (5-hmC) is a newly discovered DNA base modification in mammalian genomic DNA that is proposed to be a major epigenetic mark. We report here the syntheses of two new versions of phosphoramidites III and IV from 5-iodo-2′-deoxyuridine in 18% and 32% overall yields, respectively, with TBDMS as the 5-hydroxyl protecting group. Phosphoramidites III and IV allow efficient incorporation of 5-hmC into DNA and a "one-step" deprotection procedure to cleanly remove all the protecting groups. A "two-step" deprotection strategy is compatible with ultramild DNA synthesis, which enables the synthesis of 5hmC-containing DNA with additional modifications. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DEOXYRIBOSE
*DNA
*PHOSPHORESCENCE
*GENETICS
*GENOMICS
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 76
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 61031391
- Full Text :
- https://doi.org/10.1021/jo200566d