Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

Marzia Nuzzolo; Arnald Grabulosa; Alexandra M. Z. Slawin; Nico J. Meeuwenoord; Gijsbert A. van der Marel; Paul C. J. Kamer

doi:10.1002/ejoc.201000125

Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

Marzia Nuzzolo, Arnald Grabulosa, Alexandra M. Z. Slawin, Nico J. Meeuwenoord, Gijsbert A. van der Marel, Paul C. J. Kamer

Research output: Contribution to journal › Article › peer-review

Abstract

Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.

Original language	English
Pages (from-to)	3229-3236
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201000125
Publication status	Published - Jun 2010

Keywords

Nucleosides
Olieonucleotides
DNA
Phosphanes
Palladium
ARTIFICIAL METALLOENZYMES
ASYMMETRIC CATALYSIS
ENANTIOSELECTIVE CATALYSIS
NUCLEIC-ACIDS
NUCLEOSIDES
EVOLUTION
LINKER

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10.1002/ejoc.201000125

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title = "Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation",

abstract = "Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.",

keywords = "Nucleosides, Olieonucleotides, DNA, Phosphanes, Palladium, ARTIFICIAL METALLOENZYMES, ASYMMETRIC CATALYSIS, ENANTIOSELECTIVE CATALYSIS, NUCLEIC-ACIDS, NUCLEOSIDES, EVOLUTION, LINKER",

author = "Marzia Nuzzolo and Arnald Grabulosa and Slawin, {Alexandra M. Z.} and Meeuwenoord, {Nico J.} and {van der Marel}, {Gijsbert A.} and Kamer, {Paul C. J.}",

year = "2010",

month = jun,

doi = "10.1002/ejoc.201000125",

language = "English",

pages = "3229--3236",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "17",

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TY - JOUR

T1 - Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

AU - Nuzzolo, Marzia

AU - Grabulosa, Arnald

AU - Slawin, Alexandra M. Z.

AU - Meeuwenoord, Nico J.

AU - van der Marel, Gijsbert A.

AU - Kamer, Paul C. J.

PY - 2010/6

Y1 - 2010/6

N2 - Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.

AB - Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.

KW - Nucleosides

KW - Olieonucleotides

KW - DNA

KW - Phosphanes

KW - Palladium

KW - ARTIFICIAL METALLOENZYMES

KW - ASYMMETRIC CATALYSIS

KW - ENANTIOSELECTIVE CATALYSIS

KW - NUCLEIC-ACIDS

KW - NUCLEOSIDES

KW - EVOLUTION

KW - LINKER

UR - http://www.scopus.com/inward/record.url?scp=77952972027&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201000125

DO - 10.1002/ejoc.201000125

M3 - Article

SN - 1434-193X

SP - 3229

EP - 3236

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

Abstract

Keywords

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