Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Efficient Sonogashira Coupling Of Unprotected Halonucleosides In Aqueous Solvents Using Water‐Soluble Palladium Catalysts

J. H. Cho, Caitlin D. Prickett, K. Shaughnessy
Published 2010 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
A variety of applications of C-alkynylated nucleosides has prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient andenvironmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueous solvent. The combination of Pd(OAc)2, CuI, and TXPTS [trisodium tri(2,4-dimethyl-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromopurines and 5-iodouridine in H2O/CH3CN (1:1) in yields ranging from 42 to 98 %.
This paper references
10.1002/CHEM.200304944
Rigid, conjugated, fluoresceinated thymidine triphosphates: syntheses and polymerase mediated incorporation into DNA analogues.
L. H. Thoresen (2003)
10.1021/JO048910C
Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines.
Rebecca DeVasher (2004)
10.1021/JO00076A019
Palladium-catalyzed coupling of terminal alkynes with 5-(trifluoromethanesulfonyloxy)pyrimidine nucleosides
G. Crisp (1993)
10.1021/JM058167W
Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria.
D. Rai (2005)
10.1002/anie.200802314
Enzymatic synthesis of multiple spin-labeled DNA.
S. Obeid (2008)
10.1081/NCN-100002509
SYNTHESIS AND ADENOSINE RECEPTOR AFFINITY AND POTENCY OF 8-ALKYNYL DERIVATIVES OF ADENOSINE
C. Lambertucci (2001)
10.1080/15257770701548733
2′-Deoxyadenosine Bearing Hydrophobic Carborane Pharmacophore
Agnieszka B. Olejniczak (2007)
10.1039/A707031D
DNA duplexes stabilized by modified monomer residues: synthesis and stability
D. Graham (1998)
10.1039/B709245H
Synthesis of 2'-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions.
M. Vrabel (2007)
10.2174/1385272053765042
Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications
Kevin H. Shaughnessy and Rebecca B. DeVasher (2005)
10.2174/1570179052996955
Synthesis of Biologically Important Nucleoside Analogs by Palladium- Catalyzed C-N Bond-Formation
M. Lakshman (2005)
10.1021/BI970124X
Modified antisense oligonucleotides directed against tumor necrosis factor receptor type I inhibit tumor necrosis factor alpha-mediated functions.
J. Ojwang (1997)
10.1093/JAC/37.5.965
Pharmacokinetics of netivudine, a potent anti-varicella zoster virus drug, in patients with renal impairment.
J. P. Fillastre (1996)
10.1002/EJOC.200390025
Syntheses of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal- or Organometal-Mediated C−C Bond-Forming Reactions
Michal Hocek (2003)
10.1016/J.TET.2008.01.091
C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines: a universal linker for nucleic acids modification
Y. Saito (2008)
10.1016/J.TETLET.2006.03.100
Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring
Andrew G. Firth (2006)
10.1021/JM00359A008
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
E. De Clercq (1983)
10.1021/JO00159A012
NUCLEIC ACID RELATED COMPOUNDS. 39. EFFICIENT CONVERSION OF 5-IODO TO 5-ALKYNYL AND DERIVED 5-SUBSTITUTED URACIL BASES AND NUCLEOSIDES
M. J. Robins (1983)
10.1021/JO050832L
Inhibitory effects of the guanine moiety on Suzuki couplings of unprotected halonucleosides in aqueous media.
E. C. Western (2005)
10.1021/JA029467V
Oligo-2'-deoxyribonucleotides containing uracil modified at the 5-position with linkers ending with guanidinium groups.
V. Roig (2003)
Modified nucleosides : in biochemistry, biotechnology and medicine
P. Herdewijn (2008)
10.1021/JA039625Y
Pyrene-labeled base-discriminating fluorescent DNA probes for homogeneous SNP typing.
A. Okamoto (2004)
10.1021/JA00167A032
Palladium-catalyzed alkylations in aqueous media
A. Casalnuovo (1990)
10.1021/JA00212A053
A rigid and nonperturbing probe for duplex DNA motion
Andreas Spaltenstein (1988)
10.1016/S0022-328X(02)01267-6
Palladium-catalyzed C–N and C–C cross-couplings as versatile, new avenues for modifications of purine 2′-deoxynucleosides
M. Lakshman (2002)
10.1039/B614477B
A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs).
A. Collier (2006)
10.1021/cr800403r
Hydrophilic ligands and their application in aqueous-phase metal-catalyzed reactions.
K. Shaughnessy (2009)
10.1039/B604010A
Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines.
Petr Capek (2006)
10.1093/NAR/GKF634
Probing triplex formation by EPR spectroscopy using a newly synthesized spin label for oligonucleotides.
P. Gannett (2002)
10.1021/JM00035A010
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
G. Sági (1994)
10.1021/OL0360288
Efficient aqueous-phase Heck and Suzuki couplings of aryl bromides using tri(4,6-dimethyl-3- sulfonatophenyl)phosphine trisodium salt (TXPTS).
L. Moore (2004)
10.1080/10916460600946139
Suzuki–Miyaura Cross‐Coupling of Unprotected Halopurine Nucleosides in Water—Influence of Catalyst and Cosolvent
A. Collier (2006)
10.1021/OM7008606
Sterically Demanding, Sulfonated, Triarylphosphines: Application to Palladium-Catalyzed Cross-Coupling, Steric and Electronic Properties, and Coordination Chemistry
L. Moore (2008)
10.1021/JO034289P
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts.
E. C. Western (2003)
10.1021/JM0701472
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
W. Cristofoli (2007)
10.1081/NCN-100002534
A NEW FACILE METHOD FOR SPIN-LABELING OF OLIGONUCLEOTIDES
T. Strube (2001)
10.1016/S0960-894X(01)00347-X
Introduction of alkynyl chains on C-8 of adenosine led to very selective antagonists of the A(3) adenosine receptor.
R. Volpini (2001)
10.1021/ol9007475
Suzuki-miyaura and sonogashira coupling of 6-chloropurines and -nucleosides in water.
Jan Pschierer (2009)
10.1016/S0960-894X(00)00381-4
2'-Deoxy-8-(propyn-1-yl)adenosine-containing oligonucleotides: effects on stability of duplex and quadruplex structures.
B. Catalanotti (2000)
10.1039/B504079E
1-ethynylpyrene-modified guanine and cytosine as optical labels for DNA hybridization.
C. Wagner (2005)
10.1002/CHEM.200700220
An efficient method for the construction of functionalized DNA bearing amino acid groups through cross-coupling reactions of nucleoside triphosphates followed by primer extension or PCR.
Petr Capek (2007)
10.1039/B505737J
A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry.
N. Garg (2005)
10.1039/B705805E
Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2'-deoxyuridines fluorometrically respond to hybridization.
R. E. Hudson (2007)
10.1016/J.TETLET.2008.01.124
Synthesis and reversible photoisomerization of photoswitchable nucleoside, 8-styryl-2′-deoxyguanosine
Shinzi Ogasawara (2008)
10.1016/J.TETLET.2004.03.071
Fluorescent oligonucleotide incorporating 5-(1-ethynylpyrenyl)-2'-deoxyuridine: sequence-specific fluorescence changes upon duplex formation
G. T. Hwang (2004)
10.1021/CR010374Q
Palladium-assisted routes to nucleosides.
L. Agrofoglio (2003)
10.1021/JM970434D
N2- and C8-substituted oligodeoxynucleotides with enhanced thrombin inhibitory activity in vitro and in vivo.
G. He (1998)



This paper is referenced by
10.1002/9783527677894.CH10
The Sonogashira Reaction
R. Chinchilla (2014)
10.1021/cr400133p
Chemicals from alkynes with palladium catalysts.
R. Chinchilla (2014)
Squaraine Dyes, Design And Synthesis For Various Functional Materials Applications
Y. Zhang (2013)
10.1016/J.TETLET.2012.01.106
One-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides in aqueous conditions
Nathalie Fresneau (2012)
10.1080/15257770.2010.548844
Interrogation of a Sonogashira Cross-Coupling of 8-Bromoguanosine with Phenylacetylene on Amberlite: Evidence for Pd/Cu Ion Binding and Propagation of Pd/Cu Nanoparticles
Andrew G. Firth (2011)
10.1002/EJOC.201201384
Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions
Bappaditya Nandi (2013)
10.1021/jm301311c
Phthalocyanine-peptide conjugates: receptor-targeting bifunctional agents for imaging and photodynamic therapy.
E. Ranyuk (2013)
10.3390/CATAL7030074
The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization
T. Willemse (2017)
10.1002/047084289X.RN01518
1‐Trimethylammonium‐2‐(di‐t‐butyl)phosphino)ethane Chloride, t‐Bu‐Amphos
K. Shaughnessy (2013)
10.3390/molecules25071645
Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes
Shatrughn Bhilare (2020)
10.1002/9783527656790.CH2
Metal‐Catalyzed C–H Bond Activation and C–C Bond Formation in Water
B. Li (2013)
10.1016/J.TET.2013.06.100
Synthesis of the first conjugates of 5-ethynyl-2′-deoxyuridine with closo-dodecaborate and cobalt-bis-dicarbollide boron clusters
A. Semioshkin (2013)
10.1002/chem.201904700
Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA
A. Šimonová (2019)
10.1039/c1cs15071e
Recent advances in Sonogashira reactions.
R. Chinchilla (2011)
10.1016/J.TETLET.2010.11.110
Synthesis of symmetrical diarylalkyne from palladium-catalyzed decarboxylative couplings of propiolic acid and aryl bromides under water
K. Park (2011)
10.1002/ajoc.202000016
Carbazole‐Based N‐Heterocyclic Carbenes for the Promotion of Copper‐Catalyzed Palladium‐Free Homo‐/Hetero‐Coupling of Alkynes and Sonogashira Reactions
T. R. Girase (2020)
10.1186/S40508-015-0029-2
Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides
G. Hervé (2015)
10.1016/j.bmc.2012.08.021
Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides.
M. Tichý (2012)
10.1039/C6RA19039A
Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides
Shatrughn Bhilare (2016)
10.1002/cbdv.201700335
Synthesis of 8‐Substituted 2′‐Deoxyisoguanosines via Unprotected 8‐Brominated 2‐Amino‐2′‐deoxyadenosine
W. Zhang (2018)
10.1002/0471142700.nc0127s49
Aqueous‐Phase Sonogashira Alkynylation to Synthesize 5‐Substituted Pyrimidine and 8‐Substituted Purine Nucleosides
J. H. Cho (2012)
10.3390/molecules20059419
Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides
K. Shaughnessy (2015)
10.1002/chem.201403003
Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors.
Y. Zhang (2014)
10.1002/9783527648283.CH7
Cross‐Coupling Reactions in Aqueous Media
K. Shaughnessy (2013)
10.1002/EJOC.201100367
Thermoregulated Copper-Free Sonogashira Coupling in Water
N. Liu (2011)
10.1002/9783527656790.CH1
Metal‐Catalyzed Cross‐Couplings of Aryl Halides to Form C–C Bonds in Aqueous Media
K. Shaughnessy (2013)
10.3390/molecules171214409
Efficient Synthesis of Unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura Reaction in Aqueous Media
Nathalie Fresneau (2012)
10.1093/nar/gkaa999
Enzymatic synthesis of hypermodified DNA polymers for sequence-specific display of four different hydrophobic groups
Marek Ondruš (2020)
Semantic Scholar Logo Some data provided by SemanticScholar