scholarly journals Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and their Effect on RNA and DNA Triplex Stability

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 580
Author(s):  
Lotta Granqvist ◽  
Ville Tähtinen ◽  
Pasi Virta

Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-1′′→6, 3′ and 4′) neamines) have been synthesized in a straightforward manner. Peracetylated neomycin azide was used as a common starting material to obtain neobiosamine glycosyl donor and 6, 3′,4′-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4′-, 5,3′,4′- and 5,6,3′-tri-O-acetyl neamine azide). Glycosylation between the neobiosamine glycosyl donor and the neamine-derived acceptors gave the protected pseudo-tetrasaccharides, which were converted, via global deprotection (deacetylation and reduction of the azide groups), to the desired site isomers of neomycin. The effect of these aminoglycosides on the RNA and DNA triplex stability was studied by UV-melting profile analysis.

1969 ◽  
Vol 4 (1) ◽  
pp. 71-87 ◽  
Author(s):  
L. BOLUND ◽  
N. R. RINGERTZ ◽  
H. HARRIS

When the nucleus of a chick erythrocyte is introduced into the cytoplasm of a HeLa cell it resumes the synthesis of RNA and DNA. This reactivation of the red cell nucleus is associated with an increase in volume and with changes in nuclear composition. These changes have now been studied by quantitative cytochemical techniques. During the process of reactivation the dry mass of the erythrocyte nucleus shows a marked increase which takes place largely before the replication of the DNA begins. Within 24 h of cell fusion, some erythrocyte nuclei already contain an increased amount of DNA, and 48 h after fusion many of them contain twice the normal diploid amount, thus indicating that they have replicated their DNA completely. The physical properties of the nuclear deoxyribonucleoprotein complex also change. The ability of the nuclear chromatin to bind acridine orange increases 4- to 5-fold well before the synthesis of DNA begins; and changes in the melting profile of the deoxyribonucleoprotein suggest that its structure is loosened. This view is also supported by the observation that the reactivity of the erythrocyte nuclei to the Feulgen stain is altered during the early stages of reactivation.


2015 ◽  
Vol 19 (6) ◽  
pp. 419-425 ◽  
Author(s):  
Pawel Borun ◽  
Kacper Salanowski ◽  
Dariusz Godlewski ◽  
Jaroslaw Walkowiak ◽  
Andrzej Plawski

2017 ◽  
Vol 13 ◽  
pp. 855-862 ◽  
Author(s):  
Chuang Li ◽  
Haixin Ding ◽  
Zhizhong Ruan ◽  
Yirong Zhou ◽  
Qiang Xiao

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-α-D-ribofuranose. For the first time, ortho-alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbrüggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph3PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.


1988 ◽  
Vol 66 (7) ◽  
pp. 1675-1685 ◽  
Author(s):  
William A. Ayer ◽  
Francisco X. Talamas

The chiral resin acid levopimaric acid (1), isolated from pine oleoresin, is used as a starting material for the synthesis of (−)-warburganal (2). The synthesis proceeds via the endoperoxide of methyl levopimarate, which after ozonolysis, protection of the resulting aldehyde function, reduction, and treatment with sodium methoxide provides the tetranorditerpenoid 12a. The hemiacetal 12a is then transformed to a mixture of hemithioacetals. At this point the carbomethoxyl group at C-4 is reduced to a methyl group, and then a C-11, C-12 double bond is introduced. Ozonolysis followed by elimination of formic acid provides a mixture of olefins (27) that is hydroxylated at C-9. Removal of the protecting group then gives (−)-warburganal (2). The sequence requires 15 steps and the overall yield from levopimaric acid to warburganal is 2.7%.


2017 ◽  
Vol 13 ◽  
pp. 1239-1279 ◽  
Author(s):  
A Michael Downey ◽  
Michal Hocek

Glycosylation is an immensely important biological process and one that is highly controlled and very efficient in nature. However, in a chemical laboratory the process is much more challenging and usually requires the extensive use of protecting groups to squelch reactivity at undesired reactive moieties. Nonetheless, by taking advantage of the differential reactivity of the anomeric center, a selective activation at this position is possible. As a result, protecting group-free strategies to effect glycosylations are available thanks to the tremendous efforts of many research groups. In this review, we showcase the methods available for the selective activation of the anomeric center on the glycosyl donor and the mechanisms by which the glycosylation reactions take place to illustrate the power these techniques.


2016 ◽  
Vol 2016 ◽  
pp. 1-8 ◽  
Author(s):  
Jing Wang ◽  
Xiaoming Pan ◽  
Xingguo Liang

High resolution melting (HRM), with a high sensitivity to distinguish the nucleic acid species with small variations, has been widely applied in the mutation scanning, methylation analysis, and genotyping. For the aim of extending HRM for the evaluation of thermal stability of nucleic acid secondary structures on sequence dependence, we investigated effects of the dye of EvaGreen, metal ions, and impurities (such as dNTPs) on melting temperature (Tm) measurement by HRM. The accuracy of HRM was assessed as compared with UV melting method, and little difference between the two methods was found when the DNA Tm was higher than 40°C. Both insufficiency and excessiveness of EvaGreen were found to give rise to a little bit higher Tm, showing that the proportion of dye should be considered for precise Tm measurement of nucleic acids. Finally, HRM method was also successfully used to measure Tms of DNA triplex, hairpin, and RNA duplex. In conclusion, HRM can be applied in the evaluation of thermal stability of nucleic acid (DNA or RNA) or secondary structural elements (even when dNTPs are present).


Author(s):  
S.F. Corcoran

Over the past decade secondary ion mass spectrometry (SIMS) has played an increasingly important role in the characterization of electronic materials and devices. The ability of SIMS to provide part per million detection sensitivity for most elements while maintaining excellent depth resolution has made this technique indispensable in the semiconductor industry. Today SIMS is used extensively in the characterization of dopant profiles, thin film analysis, and trace analysis in bulk materials. The SIMS technique also lends itself to 2-D and 3-D imaging via either the use of stigmatic ion optics or small diameter primary beams.By far the most common application of SIMS is the determination of the depth distribution of dopants (B, As, P) intentionally introduced into semiconductor materials via ion implantation or epitaxial growth. Such measurements are critical since the dopant concentration and depth distribution can seriously affect the performance of a semiconductor device. In a typical depth profile analysis, keV ion sputtering is used to remove successive layers the sample.


Crisis ◽  
2020 ◽  
Vol 41 (4) ◽  
pp. 288-295 ◽  
Author(s):  
Nadia Bounoua ◽  
Jasmeet P. Hayes ◽  
Naomi Sadeh

Abstract. Background: Suicide among veterans has increased in recent years, making the identification of those at greatest risk for self-injurious behavior a high research priority. Aims: We investigated whether affective impulsivity and risky behaviors distinguished typologies of self-injurious thoughts and behaviors in a sample of trauma-exposed veterans. Method: A total of 95 trauma-exposed veterans (ages 21–55; 87% men) completed self-report measures of self-injurious thoughts and behaviors, impulsivity, and clinical symptoms. Results: A latent profile analysis produced three classes that differed in suicidal ideation, suicide attempts and nonsuicidal self-injury (NSSI): A low class that reported little to no self-injurious thoughts or behaviors; a self-injurious thoughts (ST) class that endorsed high levels of ideation but no self-harm behaviors; and a self-injurious thoughts and behaviors (STaB) class that reported ideation, suicide attempts and NSSI. Membership in the STaB class was associated with greater affective impulsivity, disinhibition, and distress/arousal than the other two classes. Limitations: Limitations include an overrepresentation of males in our sample, the cross-sectional nature of the data, and reliance on self-report measures. Conclusion: Findings point to affective impulsivity and risky behaviors as important characteristics of veterans who engage in self-injurious behaviors.


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