Oligodeoxynucleotides containing a-L-ribo configured LNA-type C-aryl nucleotides

Raunak, Bolle Ravindra Babu, M.D. Sørensen, V.S. Parmar, N.H. Harrit, Jesper Wengel

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Synthesis of 2′-O,4′-C-methylene-α-L-ribofuranosyl derivatives containing phenyl and 1-pyrenyl aglycons, i.e., novel α-L-ribo configured LNA-type C-aryl nucleosides, has been accomplished. Key synthetic steps included stereoselective Grignard reactions on tetrahydrofuran aldehyde 12, configurational inversion of the resulting alcohol 13 into alcohol 15, and concomitant Mitsonobu cyclization furnishing the desired bicyclic furanosyl skeleton with a locked conformation. The phosphoramidite derivatives 19a and 19b were used for automated synthesis of 9-mer DNA and α-L-LNA oligonucleotides containing the α-L-LNA-type C-aryl monomers αLPhL and αLPyL containing a phenyl and pyrenyl aglycon, respectively. Thermal denaturation studies showed universal base pairing behavior for the pyrenyl monomer αLPyL when incorporated into a DNA or an α-L-LNA oligonucleotide.

Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume2004
Issue number1
Pages (from-to)80-89
ISSN1477-0520
DOIs
Publication statusPublished - 2004

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Oligodeoxyribonucleotides
Oligonucleotides
Nucleotides
Monomers
Alcohols
Derivatives
Denaturation
DNA
Cyclization
Nucleosides
Aldehydes
Conformations
phosphoramidite
tetrahydrofuran
Hot Temperature

Cite this

Raunak ; Babu, Bolle Ravindra ; Sørensen, M.D. ; Parmar, V.S. ; Harrit, N.H. ; Wengel, Jesper. / Oligodeoxynucleotides containing a-L-ribo configured LNA-type C-aryl nucleotides. In: Organic & Biomolecular Chemistry. 2004 ; Vol. 2004, No. 1. pp. 80-89.
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title = "Oligodeoxynucleotides containing a-L-ribo configured LNA-type C-aryl nucleotides",
abstract = "Synthesis of 2′-O,4′-C-methylene-α-L-ribofuranosyl derivatives containing phenyl and 1-pyrenyl aglycons, i.e., novel α-L-ribo configured LNA-type C-aryl nucleosides, has been accomplished. Key synthetic steps included stereoselective Grignard reactions on tetrahydrofuran aldehyde 12, configurational inversion of the resulting alcohol 13 into alcohol 15, and concomitant Mitsonobu cyclization furnishing the desired bicyclic furanosyl skeleton with a locked conformation. The phosphoramidite derivatives 19a and 19b were used for automated synthesis of 9-mer DNA and α-L-LNA oligonucleotides containing the α-L-LNA-type C-aryl monomers αLPhL and αLPyL containing a phenyl and pyrenyl aglycon, respectively. Thermal denaturation studies showed universal base pairing behavior for the pyrenyl monomer αLPyL when incorporated into a DNA or an α-L-LNA oligonucleotide.",
author = "Raunak and Babu, {Bolle Ravindra} and M.D. S{\o}rensen and V.S. Parmar and N.H. Harrit and Jesper Wengel",
year = "2004",
doi = "10.1039/B310719A",
language = "English",
volume = "2004",
pages = "80--89",
journal = "Organic & Biomolecular Chemistry",
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publisher = "Royal Society of Chemistry",
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Oligodeoxynucleotides containing a-L-ribo configured LNA-type C-aryl nucleotides. / Raunak; Babu, Bolle Ravindra; Sørensen, M.D.; Parmar, V.S.; Harrit, N.H.; Wengel, Jesper.

In: Organic & Biomolecular Chemistry, Vol. 2004, No. 1, 2004, p. 80-89.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Oligodeoxynucleotides containing a-L-ribo configured LNA-type C-aryl nucleotides

AU - Raunak, null

AU - Babu, Bolle Ravindra

AU - Sørensen, M.D.

AU - Parmar, V.S.

AU - Harrit, N.H.

AU - Wengel, Jesper

PY - 2004

Y1 - 2004

N2 - Synthesis of 2′-O,4′-C-methylene-α-L-ribofuranosyl derivatives containing phenyl and 1-pyrenyl aglycons, i.e., novel α-L-ribo configured LNA-type C-aryl nucleosides, has been accomplished. Key synthetic steps included stereoselective Grignard reactions on tetrahydrofuran aldehyde 12, configurational inversion of the resulting alcohol 13 into alcohol 15, and concomitant Mitsonobu cyclization furnishing the desired bicyclic furanosyl skeleton with a locked conformation. The phosphoramidite derivatives 19a and 19b were used for automated synthesis of 9-mer DNA and α-L-LNA oligonucleotides containing the α-L-LNA-type C-aryl monomers αLPhL and αLPyL containing a phenyl and pyrenyl aglycon, respectively. Thermal denaturation studies showed universal base pairing behavior for the pyrenyl monomer αLPyL when incorporated into a DNA or an α-L-LNA oligonucleotide.

AB - Synthesis of 2′-O,4′-C-methylene-α-L-ribofuranosyl derivatives containing phenyl and 1-pyrenyl aglycons, i.e., novel α-L-ribo configured LNA-type C-aryl nucleosides, has been accomplished. Key synthetic steps included stereoselective Grignard reactions on tetrahydrofuran aldehyde 12, configurational inversion of the resulting alcohol 13 into alcohol 15, and concomitant Mitsonobu cyclization furnishing the desired bicyclic furanosyl skeleton with a locked conformation. The phosphoramidite derivatives 19a and 19b were used for automated synthesis of 9-mer DNA and α-L-LNA oligonucleotides containing the α-L-LNA-type C-aryl monomers αLPhL and αLPyL containing a phenyl and pyrenyl aglycon, respectively. Thermal denaturation studies showed universal base pairing behavior for the pyrenyl monomer αLPyL when incorporated into a DNA or an α-L-LNA oligonucleotide.

U2 - 10.1039/B310719A

DO - 10.1039/B310719A

M3 - Journal article

VL - 2004

SP - 80

EP - 89

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 1

ER -