5′-porphyrin-oligonucleotide conjugates

Neutral porphyrin-DNA interactions

Milan Balaz, Jay D. Steinkruger, George A. Ellestad, Nina Berova

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5′-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.

Original languageEnglish
Pages (from-to)5613-5616
Number of pages4
JournalOrganic Letters
Volume7
Issue number25
DOIs
Publication statusPublished - 2005 Dec 8

Fingerprint

oligonucleotides
Porphyrins
porphyrins
Oligonucleotides
deoxyribonucleic acid
DNA
interactions
Single-Stranded DNA
strands
Freezing
Melting point
disturbances
melting
analogs
Temperature
causes
temperature

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Balaz, Milan ; Steinkruger, Jay D. ; Ellestad, George A. ; Berova, Nina. / 5′-porphyrin-oligonucleotide conjugates : Neutral porphyrin-DNA interactions. In: Organic Letters. 2005 ; Vol. 7, No. 25. pp. 5613-5616.
@article{d4a2d1add1a44f95a0c2188a223af323,
title = "5′-porphyrin-oligonucleotide conjugates: Neutral porphyrin-DNA interactions",
abstract = "(Chemical Equation Presented) Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5′-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.",
author = "Milan Balaz and Steinkruger, {Jay D.} and Ellestad, {George A.} and Nina Berova",
year = "2005",
month = "12",
day = "8",
doi = "10.1021/ol0522992",
language = "English",
volume = "7",
pages = "5613--5616",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "25",

}

5′-porphyrin-oligonucleotide conjugates : Neutral porphyrin-DNA interactions. / Balaz, Milan; Steinkruger, Jay D.; Ellestad, George A.; Berova, Nina.

In: Organic Letters, Vol. 7, No. 25, 08.12.2005, p. 5613-5616.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 5′-porphyrin-oligonucleotide conjugates

T2 - Neutral porphyrin-DNA interactions

AU - Balaz, Milan

AU - Steinkruger, Jay D.

AU - Ellestad, George A.

AU - Berova, Nina

PY - 2005/12/8

Y1 - 2005/12/8

N2 - (Chemical Equation Presented) Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5′-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.

AB - (Chemical Equation Presented) Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5′-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.

UR - http://www.scopus.com/inward/record.url?scp=29544447719&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=29544447719&partnerID=8YFLogxK

U2 - 10.1021/ol0522992

DO - 10.1021/ol0522992

M3 - Article

VL - 7

SP - 5613

EP - 5616

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 25

ER -