Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides and Oligodipeptoids Tagged with Triazines as Recognition Elements

Pairing up: Oligodipeptide, oligodeoxydipeptide, or oligodipeptoid backbones tagged with the 2,4‐diaminotriazine nucleus pair strongly with complementary DNA and RNA. This is in sharp contrast with the behavior of the 2,4‐dioxotriazine nucleus, which does not act as a nucleobase in these systems....

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Published inAngewandte Chemie (International ed.) Vol. 46; no. 14; pp. 2470 - 2477
Main Authors Mittapalli, Gopi Kumar, Reddy, Kondreddi Ravinder, Xiong, Hui, Munoz, Omar, Han, Bo, De Riccardis, Francesco, Krishnamurthy, Ramanarayanan, Eschenmoser, Albert
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
Base Pairing
Chemistry
Chemistry, Multidisciplinary
Dipeptides - chemistry
DNA
oligonucleotides
Oligopeptides - chemistry
Peptoids - chemistry
Physical Sciences
RNA
Science & Technology
triazines
Triazines - chemistry
PEPTIDE NUCLEIC-ACIDS
PNA ANALOGS
RNA
PREBIOTIC SYNTHESIS
oligonucleotides
HYBRIDIZATION PROPERTIES
base pairing
CHEMICAL ETIOLOGY
triazines
BASE-PAIRS
DNA
MOLECULAR RECOGNITION
PAIRING PROPERTIES
Online AccessGet full text

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Abstract Pairing up: Oligodipeptide, oligodeoxydipeptide, or oligodipeptoid backbones tagged with the 2,4‐diaminotriazine nucleus pair strongly with complementary DNA and RNA. This is in sharp contrast with the behavior of the 2,4‐dioxotriazine nucleus, which does not act as a nucleobase in these systems.
AbstractList Pairing up: Oligodipeptide, oligodeoxydipeptide, or oligodipeptoid backbones tagged with the 2,4‐diaminotriazine nucleus pair strongly with complementary DNA and RNA. This is in sharp contrast with the behavior of the 2,4‐dioxotriazine nucleus, which does not act as a nucleobase in these systems.
Author Krishnamurthy, Ramanarayanan
Reddy, Kondreddi Ravinder
De Riccardis, Francesco
Mittapalli, Gopi Kumar
Eschenmoser, Albert
Xiong, Hui
Munoz, Omar
Han, Bo
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  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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  surname: Reddy
  fullname: Reddy, Kondreddi Ravinder
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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  surname: Xiong
  fullname: Xiong, Hui
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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  surname: Munoz
  fullname: Munoz, Omar
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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  givenname: Bo
  surname: Han
  fullname: Han, Bo
  organization: Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, HCI Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1043
– sequence: 6
  givenname: Francesco
  surname: De Riccardis
  fullname: De Riccardis, Francesco
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
– sequence: 7
  givenname: Ramanarayanan
  surname: Krishnamurthy
  fullname: Krishnamurthy, Ramanarayanan
  email: rkrishna@scripps.edu
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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  givenname: Albert
  surname: Eschenmoser
  fullname: Eschenmoser, Albert
  email: Eschenmoser@org.chem.ethz.ch
  organization: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
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Issue 14
Keywords PEPTIDE NUCLEIC-ACIDS
PNA ANALOGS
RNA
PREBIOTIC SYNTHESIS
oligonucleotides
HYBRIDIZATION PROPERTIES
base pairing
CHEMICAL ETIOLOGY
triazines
BASE-PAIRS
DNA
MOLECULAR RECOGNITION
PAIRING PROPERTIES
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ArticleID:ANIE200603207
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Chemistry of α-Aminonitriles, Part 45. For part 44, see reference  1a; for part 43, see reference  1b. This work was supported by the Skaggs Research Foundation. G.K.M., K.R.R., H.X., O.M., and F.D.R. are Skaggs Postdoctoral Fellows.
1a
1b
Chemistry of α‐Aminonitriles, Part 45. For part 44, see reference
for part 43, see reference
This work was supported by the Skaggs Research Foundation. G.K.M., K.R.R., H.X., O.M., and F.D.R. are Skaggs Postdoctoral Fellows.
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Snippet Pairing up: Oligodipeptide, oligodeoxydipeptide, or oligodipeptoid backbones tagged with the 2,4‐diaminotriazine nucleus pair strongly with complementary DNA...
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SubjectTerms Base Pairing
Chemistry
Chemistry, Multidisciplinary
Dipeptides - chemistry
DNA
oligonucleotides
Oligopeptides - chemistry
Peptoids - chemistry
Physical Sciences
RNA
Science & Technology
triazines
Triazines - chemistry
Title Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides and Oligodipeptoids Tagged with Triazines as Recognition Elements
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Volume 46
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