Communication

Synthesis of 2′-Deoxy-5-(methylselenyl)cytidine and Se-DNAs for Structural and Functional Studies

  1. Wen Zhang,
  2. Jia Sheng,
  3. Abdalla E. Hassan,
  4. Zhen Huang*

Article first published online: 13 JAN 2012

DOI: 10.1002/asia.201100898

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 3, pages 476–479, March 5, 2012

Additional Information

How to Cite

Zhang, W., Sheng, J., Hassan, A. E. and Huang, Z. (2012), Synthesis of 2′-Deoxy-5-(methylselenyl)cytidine and Se-DNAs for Structural and Functional Studies. Chem. Asian J., 7: 476–479. doi: 10.1002/asia.201100898

Author Information

  1. Department of Chemistry, Georgia State University, Atlanta, Georgia 30303 (USA)

*Department of Chemistry, Georgia State University, Atlanta, Georgia 30303 (USA)

Publication History

  1. Issue published online: 29 FEB 2012
  2. Article first published online: 13 JAN 2012
  3. Manuscript Received: 3 NOV 2011

Funded by

  • Georgia Cancer Coalition (GCC)
  • NIH. Grant Number: GM095086
  • NSF. Grant Number: MCB-0824837

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Keywords:

  • 5-methyl cytidine;
  • DNA methylation;
  • epigenetics;
  • structure elucidation;
  • X-ray diffraction
Thumbnail image of graphical abstract

It's not in your DNA: We report here the synthesis of a novel 5-methyl deoxycytidine analog and its phosphoramidite modified with selenium at the C-5 position (SeC). Incorporation of SeC into DNA does not cause structural perturbations, as shown by X-ray crystallography and in agreement with UV melting data. The Se modification provides a useful strategy for biochemical and structural investigations on 5-methylation of cytidine.

Featured Compounds

Compound 1
Molecular Weight:436.4141
Molecular Formula:C23H20N2O7
InChIKey:WTTRUBICDWFROZ-NLWGTHIKSA-N
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Compound 2
Molecular Weight:737.82
Molecular Formula:C37H46N2O7SeSi
InChIKey:WHIFMROEWGPTBP-RKKDRKJOSA-N
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Compound 4
Molecular Weight:726.68
Molecular Formula:C38H37N3O7Se
InChIKey:VTGJJMRMMTVKSM-VOTWKOMSSA-N
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Compound 5
Molecular Weight:926.89
Molecular Formula:C47H54N5O8PSe
InChIKey:SSSYOWCIPCCUOX-KLCPBANFSA-N
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Compound 6
Molecular Weight:476.13
Molecular Formula:C10H15N3O10P2Se
InChIKey:Not Available
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Compound 3
Molecular Weight:840.94
Molecular Formula:C44H51N3O7SeSi
InChIKey:WDPUIHZYAJBDGL-OPWUGURCSA-N
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View Full Article with Supporting Information (HTML) Get PDF (456K)