DNA and RNA can be equally efficient catalysts for carbon-carbon bond formation

Madhavaiah Chandra, Scott K. Silverman

Research output: Contribution to journalArticle

Abstract

We report the in vitro selection of deoxyribozymes that catalyze the Diels-Alder reaction between anthracene and maleimide substrates. Previous work showed that ribozymes can catalyze this reaction with substantial rate enhancement. We viewed the direct comparison of DNA and RNA enzymes as an opportunity to test the relative catalytic efficiencies of DNA and RNA. Many new deoxyribozymes were identified; one of these, DAB22, can catalyze the in trans reaction of untethered anthracene and maleimide substrates with rate constant and rate enhancement values comparable to those of the analogous ribozyme (e.g., kobs 3 min-1 and rate enhancement > 4 × 105 for the deoxyribozyme). These findings provide evidence that DNA enzymes can catalyze carbon-carbon bond formation as efficiently as the best known RNA enzymes, despite the absence of 2′-hydroxyl groups in DNA.

Original languageEnglish (US)
Pages (from-to)2936-2937
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number10
DOIs
StatePublished - Mar 12 2008

Fingerprint

Catalytic DNA
RNA
Catalytic RNA
DNA
Carbon
catalyst
Catalysts
Enzymes
Anthracene
carbon
enzyme
substrate
Cycloaddition Reaction
Substrates
Hydroxyl Radical
Rate constants
rate
maleimide
anthracene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

DNA and RNA can be equally efficient catalysts for carbon-carbon bond formation. / Chandra, Madhavaiah; Silverman, Scott K.

In: Journal of the American Chemical Society, Vol. 130, No. 10, 12.03.2008, p. 2936-2937.

Research output: Contribution to journalArticle

@article{6afadd06f9804509acd506f9fbabee41,
title = "DNA and RNA can be equally efficient catalysts for carbon-carbon bond formation",
abstract = "We report the in vitro selection of deoxyribozymes that catalyze the Diels-Alder reaction between anthracene and maleimide substrates. Previous work showed that ribozymes can catalyze this reaction with substantial rate enhancement. We viewed the direct comparison of DNA and RNA enzymes as an opportunity to test the relative catalytic efficiencies of DNA and RNA. Many new deoxyribozymes were identified; one of these, DAB22, can catalyze the in trans reaction of untethered anthracene and maleimide substrates with rate constant and rate enhancement values comparable to those of the analogous ribozyme (e.g., kobs 3 min-1 and rate enhancement > 4 × 105 for the deoxyribozyme). These findings provide evidence that DNA enzymes can catalyze carbon-carbon bond formation as efficiently as the best known RNA enzymes, despite the absence of 2′-hydroxyl groups in DNA.",
author = "Madhavaiah Chandra and Silverman, {Scott K.}",
year = "2008",
month = "3",
day = "12",
doi = "10.1021/ja7111965",
language = "English (US)",
volume = "130",
pages = "2936--2937",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - DNA and RNA can be equally efficient catalysts for carbon-carbon bond formation

AU - Chandra, Madhavaiah

AU - Silverman, Scott K.

PY - 2008/3/12

Y1 - 2008/3/12

N2 - We report the in vitro selection of deoxyribozymes that catalyze the Diels-Alder reaction between anthracene and maleimide substrates. Previous work showed that ribozymes can catalyze this reaction with substantial rate enhancement. We viewed the direct comparison of DNA and RNA enzymes as an opportunity to test the relative catalytic efficiencies of DNA and RNA. Many new deoxyribozymes were identified; one of these, DAB22, can catalyze the in trans reaction of untethered anthracene and maleimide substrates with rate constant and rate enhancement values comparable to those of the analogous ribozyme (e.g., kobs 3 min-1 and rate enhancement > 4 × 105 for the deoxyribozyme). These findings provide evidence that DNA enzymes can catalyze carbon-carbon bond formation as efficiently as the best known RNA enzymes, despite the absence of 2′-hydroxyl groups in DNA.

AB - We report the in vitro selection of deoxyribozymes that catalyze the Diels-Alder reaction between anthracene and maleimide substrates. Previous work showed that ribozymes can catalyze this reaction with substantial rate enhancement. We viewed the direct comparison of DNA and RNA enzymes as an opportunity to test the relative catalytic efficiencies of DNA and RNA. Many new deoxyribozymes were identified; one of these, DAB22, can catalyze the in trans reaction of untethered anthracene and maleimide substrates with rate constant and rate enhancement values comparable to those of the analogous ribozyme (e.g., kobs 3 min-1 and rate enhancement > 4 × 105 for the deoxyribozyme). These findings provide evidence that DNA enzymes can catalyze carbon-carbon bond formation as efficiently as the best known RNA enzymes, despite the absence of 2′-hydroxyl groups in DNA.

UR - http://www.scopus.com/inward/record.url?scp=41449109957&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=41449109957&partnerID=8YFLogxK

U2 - 10.1021/ja7111965

DO - 10.1021/ja7111965

M3 - Article

C2 - 18271591

AN - SCOPUS:41449109957

VL - 130

SP - 2936

EP - 2937

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 10

ER -