Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs

Tawarada, Ryuya; Seio, Kohji; Sekine, Mitsuo

doi:10.1021/jo701634t

Cited by 37 publications

(26 citation statements)

References 28 publications

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“…Thus halogen bonding opens up new insights to materials design and synthesis not only in the solid state but also for soft materials, such as liquid crystals. The significance of halogen bonding in biological systems has very recently attracted attention 36,37 thus further generalizing the concept of halogen bonding. Most recent review by the Milan group summarizes the most recent results and future prospects.…”

Section: Discussionmentioning

confidence: 99%

Halogen bonded supramolecular complexes and networks

2008

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Section: Discussionmentioning

confidence: 99%

Halogen bonded supramolecular complexes and networks

2008

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“…An umber of planar N-heterocycles, such as pyrrole, imidazole, 1,2,4-triazole, and 1-H-tetrazole were reacted with the Michael acceptor 6 andt he products were isolated as isonucleosides 27 a-d,r espectively,i nm oderate yields (Scheme 9). It should be noted that as ignificantn umber of pyrrole, [31] imidazole, [32] triazole, [33] and tetrazole [34] nucleosides have been shown to exhibit broad biological activity.H owever,t heir isonucleoside derivatives are less known [35] and examples of glyco isonucleosides are also rare. The pyranoside 12,o ns imilar treatment with imidazole, 1,2,4-triazole, 1-H-tetrazole, and the nucleobase thymine, afforded isonucleosides 28 b-e,r espectively (Scheme 9).…”

Section: Resultsmentioning

confidence: 99%

Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

2016

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d-Fructose, an inexpensive biomass precursor available on al arge scale, has been used for the generation of enantiomerically pure chemical entities. Construction of vinyl selenone moieties on cyclic skeletons of d-fructose led to the highly reactive synthetic intermediates comprisingo f an electron-deficient double bond along with an excellent leaving group. Reactions of these Michael acceptors with dif-ferent nucleophiles afforded aziridines, thiiranes,c yclopropanes, dihydrofurans, dihydroisoxazole, dibenzyloxymethylfuran, and isonucleosides in moderate to good yields. This powerful and practical route provides an ew platform for synthetic applicationso fr enewable biomass precursors and adds to the toolbox for chemists interested in new chemical entities. Supportinginformation for this article can be found under http:// dx.doi.org/10.1002/ajoc.201600183.I tc ontains 1 Ha nd 13 CNMR spectra of all new compounds, COSYs pectra( for 18 b, 20 a, 24,a nd 27 c), NOESY spectrum(for 17 c), 1D NOE difference spectra (for 18 b, 20 a,and 24), and ORTEP diagrams (for 15 h, 17 a, 22,and 30 b).populara ldoses such as d-glucose, d-mannose, d-ribose, dxylose, etc. Ac hiral ketones ynthesized from d-fructose [9] rapidly developed into an ew class of asymmetric epoxidation catalyst forthe epoxidation of olefins ( Figure 2). [10] Fructose-derived chiral 1,3-oxazolidine-2-thiones (OZTs) are also used as chiral substrates in coupling reactions ( Figure 2). [11] 1,5-Anhydro-dfructose( 1,5-AnFru) [12] and di-d-fructose dianhydrides (DFAs) [2, 13] are important precursors for the synthesis of new carbohydrate derivatives (Figure 2).We have been designing methodsf or accessing enantiopure oxaheterocycles, [14] carbocycles, [15, 16] aza-and thia-heterocycles, [16, 17] pyrroles, [18] and 1,5-disubstituted-1,2,3-triazoles [19] from monosaccharides. In line with the utilization of sugar molecules as "chiral pools"i ns ynthetic chemistry, [20] our strategy wast ou se highlyr eactive vinyl sulfone-and vinyl sulfoxide-modified carbohydrates, [21] which are powerful Michael acceptors ande fficient partners in cycloaddition reactions. [15, 19] More recently,w eh ave introduced vinyl selenone-modified carbohydrates as efficient Michael acceptors in diversity oriented synthesis (DOS) to generate complex molecular scaffolds. [22] The aryl selenoyl functionality of vinyl selenone plays ad ual role as an efficient electron-withdrawing group as well as al eaving group, allowing Michael addition followed by elimination in tandem fashion. [22] Although vinyl selenones are widely used in simple systems [23] and nucleosides, [24] vinyl selenones derived from carbohydrates have rarely been utilized partly because of the notoriously unpredictable stability of carbohydrate selenones or selenoxides. [25,26] Nevertheless,w e have designed and used stable vinyl selenone-modified furanosides for generating new molecules. [22,26] As d-fructose is now considered as an intermediate for generating small molecules such as 2,5-dimethylfuran, 5-hydroxymethy...

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“…Synthesis began with the coupling of 4,5-diiodoimidazole to Hoffer’s well-known toluoyl-protected chlorosugar 30,31 to provide intermediate 11 in 84% yield (Scheme 2). Sekine et al were successful in synthesizing and isolating 11 not only in good yield, but also as the beta isomer.…”

Section: Resultsmentioning

confidence: 99%

“…Sekine et al were successful in synthesizing and isolating 11 not only in good yield, but also as the beta isomer. 30 Due to the harsh conditions present in subsequent steps however, the toluoyl groups needed to be replaced with a more robust protecting group. Although several attempts were made to replace the toluoyl group before coupling, they all resulted in poor yields, so the decision was made to replace them after coupling.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues

Wauchope

Johnson

Krishnamoorthy

et al. 2012

Bioorganic & Medicinal Chemistry

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Introducing structural diversity into the nucleoside scaffold for use as potential chemotherapeutics has long been considered an important approach to drug design. In that regard, we have designed and synthesized a number of innovative 2′-deoxy expanded nucleosides where a heteroaromatic thiophene spacer ring has been inserted in between the imidazole and pyrimidine ring systems of the natural purine scaffold. The synthetic efforts towards realizing the expanded 2′-deoxy-guanosine and -adenosine tricyclic analogues as well as the preliminary biological results are presented herein.

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Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons: Investigation of Possible Halogen Bonding Base Pairs

Cited by 37 publications

References 28 publications

Halogen bonded supramolecular complexes and networks

Halogen bonded supramolecular complexes and networks

Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues

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