4-Phenyl-m-dioxane

Shortridge, Robert W.

doi:10.1021/ja01182a518

Cited by 6 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A dramatic line-broadening is observed, with a concomitant decrease in the signal intensities. [24] In particular, we monitored the signal intensities of the aromatic resonances of the ligand upon increasing the amount of the macromolecule. As example, Figure S31A in the Supporting Information shows the decrease in the intensities of the 1 H NMR signals of 1 upon addition of increasing amounts of poly(dA-dT) 2 .…”

Section: Tr-noesy Experimentsmentioning

confidence: 99%

See 1 more Smart Citation

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

et al. 2015

View full text Add to dashboard Cite

Mannose glyco‐oligoamide β‐D‐Man‐Py‐γ‐Py‐Ind (β‐D‐Man, 1) and two new glyco‐oligoamides, β‐L‐Man‐Py‐γ‐Py‐Ind (β‐L‐Man, 2) and 6‐deoxy‐β‐D‐Man‐Py‐γ‐Py‐Ind (6‐deoxy‐β‐D‐Man, 3), have been designed and synthesized to investigate the role of hydrogen‐bonding cooperative donor centres of carbohydrates in their recognition by DNA. The free‐ and bound‐state geometries were studied, as were the affinities of the D and L enantiomers of the mannose glyco‐oligoamides (1 and 2) for DNA polymers [ct‐DNA and poly(dA‐dT)2]. TR‐NOESY and DF‐STD experiments for the diastereomeric complexes formed with DNA allow the asymmetric centres of the sugar residue that are close to the inner and outer regions of the DNA minor grooves to be distinguished. A C→N hairpin folding in β‐L‐Man derivative 2 was observed, with the α face of the sugar close to the indole ring. The C‐2 and C‐3 centres are orientated towards the inner region of the DNA minor groove. The affinity data for poly(dA‐dT)2 indicate that there is a chiral discrimination process, with β‐L‐Man derivative 2 being the best ligand. 6‐Deoxy‐β‐D‐Man derivative 3 forms the least stable complexes with DNA. Molecular dynamics simulations of β‐L‐Man derivative 2 in complex with a double‐strand dodecamer d(AT)12 are in agreement with the experimental NMR spectroscopic data. Thus, the cooperative donor centre 2‐OH in the L‐mannose enantiomer is a key contributor to the stability of the 2·poly(dA‐dT)2 complex.

show abstract

Section: Tr-noesy Experimentsmentioning

confidence: 99%

“…The dissociation constants K d were estimated using Equation (1) for data fitting, based on the procedure described by Shortridge et al [24] (1)…”

Section: Tr-noesy Experimentsmentioning

confidence: 99%

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

et al. 2015

View full text Add to dashboard Cite

show abstract

4‐Phenyl‐ m ‐Dioxane

Shriner

Ruby

2003

Organic Syntheses

View full text Add to dashboard Cite

show abstract

Copolymerization of tetraoxane with styrene catalyzed by BF₃·O(C₂H₅)₂

Higashimura

Tanaka

Miki

et al. 1967

J. Polym. Sci. A‐1 Polym. Chem.

View full text Add to dashboard Cite

The copolymerization of tetraoxane with styrene catalyzed by BF3·O(C2H5)2 was studied at 30°C. to determine whether a cyclic monomer can copolymerize with a vinyl monomer. The formation of the copolymer was confirmed by elementary analysis of both benzene‐soluble and benzene‐insoluble fractions of the polymer obtained. It was found by gas chromatography that a fairly large amount of 4‐phenyl‐1,3‐dioxane and a small amount of trioxane were formed in the present system, in addition to polymers. Roughly a third of the total amount of the monomers reacted was consumed in the formation of methanol‐insoluble polymer, a third for 4‐phenyl‐1,3‐dioxane, and another third for trioxane and unknown products which could not be indentified. The formation of these cyclic compounds during the copolymerization may be explained in terms of a back‐biting (or intramolecular transacetalization) reaction. The cationic reactivity of tetraoxane was found to be similar to that of styrene on the basis of both the consumption rate of each monomer in the copolymerizing system and the composition of the methanol‐insoluble polymer obtained.

show abstract

4-Phenyl-m-dioxane

Cited by 6 publications

References 0 publications

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

4‐Phenyl‐ m ‐Dioxane

Copolymerization of tetraoxane with styrene catalyzed by BF₃·O(C₂H₅)₂

Contact Info

Product

Resources

About

4-Phenyl-m-dioxane

Cited by 6 publications

References 0 publications

D‐ and L‐Mannose‐Containing glyco‐­Oligoamides Show Distinct Recognition Properties When Interacting with DNA

D‐ and L‐Mannose‐Containing glyco‐­Oligoamides Show Distinct Recognition Properties When Interacting with DNA

4‐Phenyl‐ m ‐Dioxane

Copolymerization of tetraoxane with styrene catalyzed by BF3·O(C2H5)2

Contact Info

Product

Resources

About

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

D‐ and L‐Mannose‐Containing glyco‐Oligoamides Show Distinct Recognition Properties When Interacting with DNA

Copolymerization of tetraoxane with styrene catalyzed by BF₃·O(C₂H₅)₂