6-Vinylated guanosine as a novel cross-linking agent and its versatile synthesis from the 6-O-tosylate by Pd(0)-catalyzed cross-coupling

Nagatsugi, Fumi; Uemura, K.; Nakashima, S.; Maëda, Minoru; Sasaki, Shigeki

doi:10.1016/0040-4039(94)02224-y

Cited by 69 publications

(16 citation statements)

References 15 publications

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“…[11] In earlier protocols, nickel complexes were mostly used as catalysts, [12] until a new class of bulky, electron-rich phosphines was discovered that strongly facilitates the oxidative addition of aryl tosylates to palladium catalysts. [13] In recent years, aryl tosylates have successfully been employed as substrates in, for example, Stille, [14] Suzuki, [15] and Kumada coupling reactions, [16] aminations, [17] and ortho-arylations. [18] The use of aryl tosylates as substrates in decarboxylative coupling reactions should have an even higher synthetic impact, when considering that a low coordinating ability of the leaving group is an essential prerequisite for accessing the full range of carboxylic acid substrates.…”

Section: In Memory Of Keith Fagnoumentioning

confidence: 99%

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Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Gooßen¹,

Rodríguez²,

Lange³

et al. 2010

Angewandte Chemie

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Section: In Memory Of Keith Fagnoumentioning

confidence: 99%

“…Shortening the reaction time to 4 hours led to a further increase in yield (compare entry 9 with entries 11 and 12). Further experiments confirmed Cu 2 O and [Pd(acac) 2 ] to be the most effective catalyst precursors, although other palladium(II) or palladium(0) compounds can be used as well (entries [13][14][15][16].…”

Section: In Memory Of Keith Fagnoumentioning

confidence: 99%

Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Gooßen¹,

Rodríguez²,

Lange³

et al. 2010

Angewandte Chemie

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“…(2) [5]. In our original design, close proximity of the 4-amino group of cytidine to the vinyl group of 1 was expected in the complex between the protonated form of 1 and cytidine to work effectively for covalent bond formation.…”

Section: Design and Synthesis Of The Reactive Nucleoside Analogmentioning

confidence: 99%

Molecular Design for Specific Recognition and Reaction in Genome-Targeting Chemistry

Sasaki¹,

Nagatsugi²

2005

Frontiers in Organic Chemistry

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Molecules that can target DNA or RNA with high efficiency and specificity are of great interest because of potential applications to modulation of gene expression at a specific site. Our approach in genome-targeting chemistry has been focused on development of reactive molecules with high base-as well as sequence selectivity. This paper summarizes our contributions in this field. At first, a general concept of reactive molecules in genome-targeting chemistry is introduced. In the following section, molecular design to achieve specific and efficient reactions in the living system is described. Two new reactive molecules, 2-amino-6-vinylpurine derivative as an efficient cross-linking agent, and the Snitroso-6-thioguanosine as a selective S to N nitoroso group transfer agent are summarized. These two molecules demonstrate successful examples of reactive agents that are activated only in the complementary hybrids. In the third section, new nucleoside analogs to expand recognition codes of triplex formation are discussed. We have recently developed non-natural nucleoside analogs (W-shaped nucleoside analog: WNA) having a heterocyclic ring as a recognition unit and an aromatic ring as a stacking part on the bicyclo[3.3.0]octane skeleton. It has been shown that the two analogs, WNA-T with a thymine and WNA-C with a cytosine, exhibit stable formation of non-natural triplexes containing a TA and a CG interrupting site with high stability, respectively. These new genome-targeting molecules will be applied to artificial modulation of gene expression in vitro as well as in vivo.

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“…In our approach to selective functional oligonucleotides, we have developed a 2-amino-6-vinylpurine (1) as a cytosine selective cross-linking agent within a duplex. 50,51) It is notable that the alkylating activity of 1 can be autogenerated within the duplex from its stable precursor, a phenylsulfide or phenylsulfoxide derivative (Fig. 3).…”

Section: Mutagenesis Using Tfos Bearing 2-amino-6-vinylpurine Derivatmentioning

confidence: 99%

Chemical Tools for Targeted Mutagenesis of DNA Based on Triple Helix Formation

Nagatsugi

Sasaki

2004

Biological & Pharmaceutical Bulletin

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6-Vinylated guanosine as a novel cross-linking agent and its versatile synthesis from the 6-O-tosylate by Pd(0)-catalyzed cross-coupling

Cited by 69 publications

References 15 publications

Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Molecular Design for Specific Recognition and Reaction in Genome-Targeting Chemistry

Chemical Tools for Targeted Mutagenesis of DNA Based on Triple Helix Formation

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