Orientierung der nitromethylgruppe in nitroalkoholen: die kristall- und molekülstrukturen von vier freien und drei acetylierten 2,6-anhydro-1-desoxy-1-nitroalditolen

Kopf, Jürgen; Topf, Cornelia; Köll, Peter

doi:10.1016/0008-6215(89)84001-7

Cited by 13 publications

(1 citation statement)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of the C -glycosides was accomplished upon reaction of the appropriate carbohydrate with nitromethane under basic conditions to provide cyclic derivatives favoring the β-pyranosylglycosides with the bulky nitromethyl group in the equatorial position. , Following an improved preparation method, C -(β- d -galactopyranosyl)- and C -(β- d -glucopyranosyl)nitromethanes ( 3 ) 20,21a,b and ( 4 ) 20,21c were obtained in yields of 50 and 53%, respectively . Hydrogenation over palladium/charcoal afforded C -(β- d -galactopyranosyl)- and C -(β- d -glucopyranosyl)methylamines ( 5 ) , and ( 6 ) , in virtually quantitative yields (Scheme )…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

Nolting

Liu

et al. 2003

Langmuir

View full text Add to dashboard Cite

As part of our continuing efforts to study the molecular events involved in HIV recognition of mucosal membrane cells, we are studying the interactions of the HIV-associated glycoprotein gp120, with the cellular receptor GalCer. In this work, we report investigations of multivalent interactions of Au glyconanoparticles containing galactosyl and glucosyl headgroups with recombinant gp120. These particles were prepared from disulfides containing C-glycosides linked to triethylene glycol via an amide bond using a modification of the Brust method. 1 Results from transmission electron microscopy, atomic force microscopy, and UV-vis absorption spectroscopy data are consistent with an average particle diameter of 2 nm. Elemental analyses indicate that the average composition of the particles is 1.6:1 Au:carbohydrate. A biotin-NeutrAvidin adhesion assay was used to evaluate the relative ability of carbohydrate disulfides and Au glyconanopraticles to displace rgp120 from plate-bound GalCer. The data indicate that divalent disulfides were less than 12% as active as biotinylated GalCer, a water-soluble surrogate of GalCer. However, when these same carbohydrates were presented in a polyvalent display on gold, they were greater than 300 times more active than the disulfides and at least 20 times more active than biotinylated GalCer. These results collectively demonstrate the potential utility of polyvalent ligand arrays on nanoplatforms.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

Nolting

Liu

et al. 2003

Langmuir

View full text Add to dashboard Cite

show abstract

¹H‐NMR spectra of all diastereomeric nitroalditols with a chain length up to C₇, obtained from aldoses by the Fischer‐Sowden reaction

et al. 1991

View full text Add to dashboard Cite

The 1H‐NMR spectra of all diastereomeric alditols with a terminal nitro group up to a chain length of seven carbon atoms (31 compounds) have been recorded at 500 MHz in D2O. In most cases, a complete first‐order analysis has been performed. The spectra show systematic correlations with those of the parent alditols. Despite a special situation around the nitromethyl group no severe deviations of preferred conformations in solution from those of the parent alditols have been observed.

show abstract

Die kristall- und molekülstrukturen von drei thermodynamisch benachteiligten 2,6-anhydronitroalditolen (“Glycopyranosylnitromethanen”)

Kopf¹,

Morf²,

Zimmer³

et al. 1990

Carbohydrate Research

View full text Add to dashboard Cite

Orientierung der nitromethylgruppe in nitroalkoholen: die kristall- und molekülstrukturen von vier freien und drei acetylierten 2,6-anhydro-1-desoxy-1-nitroalditolen

Cited by 13 publications

References 25 publications

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

¹H‐NMR spectra of all diastereomeric nitroalditols with a chain length up to C₇, obtained from aldoses by the Fischer‐Sowden reaction

Die kristall- und molekülstrukturen von drei thermodynamisch benachteiligten 2,6-anhydronitroalditolen (“Glycopyranosylnitromethanen”)

Contact Info

Product

Resources

About

Orientierung der nitromethylgruppe in nitroalkoholen: die kristall- und molekülstrukturen von vier freien und drei acetylierten 2,6-anhydro-1-desoxy-1-nitroalditolen

Cited by 13 publications

References 25 publications

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

1H‐NMR spectra of all diastereomeric nitroalditols with a chain length up to C7, obtained from aldoses by the Fischer‐Sowden reaction

Die kristall- und molekülstrukturen von drei thermodynamisch benachteiligten 2,6-anhydronitroalditolen (“Glycopyranosylnitromethanen”)

Contact Info

Product

Resources

About

¹H‐NMR spectra of all diastereomeric nitroalditols with a chain length up to C₇, obtained from aldoses by the Fischer‐Sowden reaction