Porphyrin substituted phosphoramidites

New building blocks for porphyrin-oligonucleotide syntheses

Milan Balaz, Andrea E. Holmes, Michele Benedetti, Gloria Proni, Nina Berova

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Thymidine phosphoramidites containing trispyridylphenyl and tetraphenylporphyrin chromophores attached via a short amide linker in the 3′-position have been synthesized and used as building blocks in solid-phase synthesis of self-complementary 8-mer oligonucleotides 3′-T-5′-GCGCGCA-3′ and 5′-ACGCGCGT-3′. To our knowledge, these are the first porphyrin-oligonucleotide conjugates carrying the porphyrin chromophores in the 3′-position. Chain assembly was achieved by automated solid-phase synthesis and by inexpensive straightforward 'in flask' modification of commercially available solid supported oligonucleotides. This approach allows the synthesis of modified oligonucleotides without using costly instrumentation for automated DNA synthesis. Porphyrin-containing self-complementary oligonucleotides are expected to be a valuable model for drug binding studies and determination of conformational changes in DNA sequences using circular dichroism.

Original languageEnglish
Pages (from-to)2413-2421
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number7
DOIs
Publication statusPublished - 2005 Apr 1

Fingerprint

Porphyrins
Oligonucleotides
Solid-Phase Synthesis Techniques
Chromophores
DNA sequences
Circular Dichroism
Amides
Thymidine
phosphoramidite
DNA
Pharmaceutical Preparations

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Balaz, Milan ; Holmes, Andrea E. ; Benedetti, Michele ; Proni, Gloria ; Berova, Nina. / Porphyrin substituted phosphoramidites : New building blocks for porphyrin-oligonucleotide syntheses. In: Bioorganic and Medicinal Chemistry. 2005 ; Vol. 13, No. 7. pp. 2413-2421.
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Porphyrin substituted phosphoramidites : New building blocks for porphyrin-oligonucleotide syntheses. / Balaz, Milan; Holmes, Andrea E.; Benedetti, Michele; Proni, Gloria; Berova, Nina.

In: Bioorganic and Medicinal Chemistry, Vol. 13, No. 7, 01.04.2005, p. 2413-2421.

Research output: Contribution to journalArticle

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