Antiviral Compounds. I. Aliphatic Glyoxals, α-Hydroxyaldehydes and Related Compounds

Tiffany, Burris D.; Wright, John B.; Moffett, Robert Bruce; Heinzelman, R. V.; Strube, R. E.; Aspergren, Brooke D.; Lincoln, Edward H.; White, J. L.

doi:10.1021/ja01564a042

Cited by 67 publications

(15 citation statements)

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“…c The absolute configurations of the compounds obtained by us were attributed by comparison of the sign of their measured specific rotation with those reported in the literature [6c,d]. The alpha-hydroxy-para-aminoacetophenone was observed by GC/MS analysis and NMR spectral (50% yield) [17].…”

Section: Resultsmentioning

confidence: 71%

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Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Andrade¹,

Polak²,

Porto³

et al. 2006

LOC

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The enantioselective bioreduction of alpha-substituted-acetophenones 1,2 was carried out with cells of fungi to give the corresponding chiral alcohols in good yield and high enantioselectivity (up to 99%). The chiral alcohols 3 and 4 obtained by this methodology are important intermediates for the asymmetric syntheses of chiral drugs. The enantioselectivity presented by several fungal strains was anti-Prelog.

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Section: Resultsmentioning

confidence: 71%

“…candidum was able to perform ketone and nitro reduction. For example, this fungus transformed compound 2b into two products, a mixture of (RS)-4b ( 12) and the product of the nitro group reduction and the acetate hydrolysis, alpha-hydroxy-para-aminoacetophenone [17].…”

Section: Resultsmentioning

confidence: 99%

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Andrade¹,

Polak²,

Porto³

et al. 2006

LOC

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“…Synthesis of N-Acetyl-N'-( p-gloxylylbenzoyl) cystamine p-Curboxyphenylglyoxal (GbzOH) . p-Acetyl benzoic acid (1 g; 6 mmol) was dissolved in dioxane/water (8:2 v/v) and the solution was boiled under reflux for 2 h with a 5 % molar excess (0.7 g; 6.3 mmol) of selenium dioxide [18,19]. The reaction mixture was then cooled to room temperature, and centrifuged to remove precipitated selenium, after which dry silica gel (5 g) was added and the mixture was evaporated to dryness in vucuo at 40°C.…”

Section: Buffersmentioning

confidence: 99%

“…1 The reaction sequence used to prepare Gbz-Cynz- Oxidation of p-acetylbenzoic acid to p-carboxyphenylglyoxal was achieved in good yield by treatment with selenium dioxide under reflux [18] as described by Tiffany [19]. Condensation of the crude product with cystamine was carried out in aqueous medium using a water-soluble carbodiimide to activate the carboxyl group [20], since condensation in organic solvents was found to increase side-reactions between cystamine and the aldehyde group ofp-carboxyphenylglyoxal leading to formation of polymeric products.…”

Section: Syntheses Of N-acetyl-n-(p-glyoxylylbenzoyl) -Cystamine (Gbzmentioning

confidence: 99%

Synthesis and Properties of N‐Acetyl‐N′‐(p‐glyoxylylbenzoyl)cystamine, a New Reagent for RNA‐RNA and RNA‐Protein Cross‐Linking

Expert‐Bezançon¹,

Hayes²

1980

European Journal of Biochemistry

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The synthesis of N-acetyl-N'-(p-glyoxylylbenzoy1)cystamine (Gbz-Cynz-Ac) is described. Like other glyoxal-type reagents it reacts with guanine and arginine. The kinetics and pH dependence of these reactions are studied. (Gbz-Cynz-Ac) reacts with non-base-paired guanines at about 20 sites in 16-S rRNA. After reduction of disulfide bonds each derivatized guanine residue carries a free -SH group which can be used to create RNA-RNA bridges or, after introducing an additional photoactivatable derivative, RNA-protein bridges.Analysis of ribosome structure requires the development of methods for obtaining information about the conformation of RNA and proteins, and about the mechanisms and sites of the interactions between these molecules in the intact ribosome. A number of experimental procedures have been used for this purpose and have yielded a large amount of data concerning, in particular, the proximity relationships between ribosomal proteins [l -31. However few methods for studying RNA-protein interactions and RNA conformation in the ribosome are as yet available. Among those which have given valuable results the most productive are isolation and analysis of ribonucleoprotein fragments after ribonuclease digestion of ribosomes (proximity relationships between ribo- non-base-paired sequences in an RNA react with glyoxal derivatives, and the adducts formed (see Fig. 2) are stable at acid pH but unstable at alkaline pH. Cross-links introduced between adjacent unpaired regions of an RNA chain or between RNA and protein by the use of glyoxal-based reagents are therefore easily reversible. N-Acetyl-N'-(p-glyoxylylbenzoy1)-cystamine, whose synthesis and reactivity, are described can be used to introduce such cross-links in ribosomes or in free ribosomal RNA. Its use for the analysis of the structure of 16-S RNA and 30-S ribosomal subunits of Escherichia coli will be described in subsequent publications. Several other new reagents for RNA-protein cross-linking have recently been described [15 -171 and their use will probably contribute to the identification of the sites of interaction or of proximity of ribosomal RNAs and proteins.

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“…activities [26]. It has also been shown that physiological activity of organic compounds is much enhanced on coordination to metals [25,27], particularly, Schiff bases and their metal complexes have been shown to exhibit enhanced activities [25].…”

Section: Introductionmentioning

confidence: 99%

SYNTHESIS AND CHARACTERIZATION OF SOME METAL COMPLEXES OF A SCHIFF BASE DERIVED FROM NINHYDRIN AND α ,L-ALANINE

Derebe

Raju

Retta

2002

Bull. Chem. Soc. Eth.

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ABSTRACT. Complexes of Mn(II), Fe(III), Co(II), Ni(II) and Zn(II) with an intermediate Schiff base derived from ninhydrin and a,L-alanine (indane-1,3-dione-2-imine-N-2-propionate, IDIP) were successfully synthesized. All complexes were distinctly colored and were characterized by elemental analysis, molar conductance, magnetic susceptibility, infrared and electronic spectral studies. The ligand (Schiff base) was shown to behave as a monobasic tridentate ONO donor. The Mn(II) and Fe(III) complexes contain only one ligand molecule plus water and chloride(s) per metal ion, while all the others contain two ligand molecules per metal ion. An octahedral geometry is proposed for the metal complexes.A comparative anti-microbial study of the complexes was undertaken against two gramnegative bacteria, Escherichia coli and Proteus mirabilis and one gram-positive bacterium Staphylococcus aureus. It was revealed that most of the complexes and particularly Mn(II), Fe(III) and Co(II) complexes, have a much enhanced activity relative to ninhydrin against Proteus mirabilis and Staphylococcus aureus. All complexes showed a reduced activity against Escherichia coli.

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Antiviral Compounds. I. Aliphatic Glyoxals, α-Hydroxyaldehydes and Related Compounds

Cited by 67 publications

References 0 publications

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Synthesis and Properties of N‐Acetyl‐N′‐(p‐glyoxylylbenzoyl)cystamine, a New Reagent for RNA‐RNA and RNA‐Protein Cross‐Linking

SYNTHESIS AND CHARACTERIZATION OF SOME METAL COMPLEXES OF A SCHIFF BASE DERIVED FROM NINHYDRIN AND α ,L-ALANINE

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Antiviral Compounds. I. Aliphatic Glyoxals, α-Hydroxyaldehydes and Related Compounds

Cited by 67 publications

References 0 publications

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Synthesis and Properties of N‐Acetyl‐N′‐(p‐glyoxylylbenzoyl)cystamine, a New Reagent for RNA‐RNA and RNA‐Protein Cross‐Linking

SYNTHESIS AND CHARACTERIZATION OF SOME METAL COMPLEXES OF A SCHIFF BASE DERIVED FROM NINHYDRIN AND &alpha; ,L-ALANINE

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SYNTHESIS AND CHARACTERIZATION OF SOME METAL COMPLEXES OF A SCHIFF BASE DERIVED FROM NINHYDRIN AND α ,L-ALANINE