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241.
242.
Manoharan Mathiselvam Venkatachalam Ramkumar Duraikkannu Loganathan Serge Pérez 《Glycoconjugate journal》2014,31(1):71-87
The linkage region constituents, 2-deoxy-2-acetamido-β-D-glucopyranose (GlcNAc) and L-asparagine (Asn) are conserved in the N-glycoproteins of all eukaryotes. Elucidation of the structure and conformation of the linkage region of glycoproteins is important to understand the presentation and dynamics of the carbohydrate chain at the protein/cell surface. Earlier crystallographic studies using monosaccharide models and analogs of N-glycoprotein linkage region have shown that the N-glycosidic torsion, ?N, is more influenced by the structural variation in the sugar part than that of the aglycon moiety. To access the influence of distal sugar as well as interglycosidic linkage (α or β) on the N-glycosidic torsion angles, cellobiosyl and maltosyl alkanamides have been synthesized and structural features of seven of these analogs have been characterized by X-ray crystallography. Comparative analysis of the seven disaccharide analogs with the reported monosaccharide analogs showed that the ?N value of cellobiosyl analogs deviate ~9° with respect to GlcβNHAc. In the case of maltosyl analogs, deviation is more than 18°. These deviations indicate that the N-glycosidic torsion is influenced by addition of distal sugar as well as with respect to inter glycosidic linkage (α or β); it is less influenced by changes occurring at the aglycon. The χ2 value of alkanamide derived from glucose, cellobiose and maltose exhibit a large range of variations (from 1.6° to ?109.9°). This large span of χ2 value suggests the greater degree of rotational freedom around C1′-C2′ bond which is restricted in GlcNAc alkanamides. The present finding explicitly proved the importance of molecular architecture in the N-glycoproteins linkage region to maintain the linearity, planarity and rigidity. These factors are necessary for N-glycan to serve role in inter- as well as intramolecular carbohydrate-protein interactions. 相似文献
243.
Qi Shan-Shan Manoharan Bharani Dhandapani Vignesh Jegadeesan Sridharan Rutherford Susan Wan Justin S. H. Huang Ping Dai Zhi-Cong Du Dao-Lin 《Genetica》2022,150(1):13-26
Genetica - Understanding the molecular associations underlying pathogen resistance in invasive plant species is likely to provide useful insights into the effective control of alien plants, thereby... 相似文献
244.
Muthiah Manoharan Laura K. Johnson Kathleen L. Tivel Robert H. Springer P.Dan Cook 《Bioorganic & medicinal chemistry letters》1993,3(12):2765-2770
A 2′-O-hexylthiotrityl adenosine phosphoramidite has been synthesized and incorporated into oligonucleotide phosphodiesters and phosphorothioates. This tether has potential antisense applications, offers a convenient nucleophile for conjugation of various moieties that would reside in the minor groove, and may form novel tertiary structures. 相似文献
245.
Masaaki Akabane-Nakata Namrata D Erande Pawan Kumar Rohan Degaonkar Jason A Gilbert June Qin Martha Mendez Lauren Blair Woods Yongfeng Jiang Maja
M Janas Derek K OFlaherty Ivan Zlatev Mark
K Schlegel Shigeo Matsuda Martin Egli Muthiah Manoharan 《Nucleic acids research》2021,49(5):2435
We recently reported the synthesis of 2′-fluorinated Northern-methanocarbacyclic (2′-F-NMC) nucleotides, which are based on a bicyclo[3.1.0]hexane scaffold. Here, we analyzed RNAi-mediated gene silencing activity in cell culture and demonstrated that a single incorporation of 2′-F-NMC within the guide or passenger strand of the tri-N-acetylgalactosamine-conjugated siRNA targeting mouse Ttr was generally well tolerated. Exceptions were incorporation of 2′-F-NMC into the guide strand at positions 1 and 2, which resulted in a loss of the in vitro activity. Activity at position 1 was recovered when the guide strand was modified with a 5′ phosphate, suggesting that the 2′-F-NMC is a poor substrate for 5′ kinases. In mice, the 2′-F-NMC-modified siRNAs had comparable RNAi potencies to the parent siRNA. 2′-F-NMC residues in the guide seed region position 7 and at positions 10, 11 and 12 were well tolerated. Surprisingly, when the 5′-phosphate mimic 5′-(E)-vinylphosphonate was attached to the 2′-F-NMC at the position 1 of the guide strand, activity was considerably reduced. The steric constraints of the bicyclic 2′-F-NMC may impair formation of hydrogen-bonding interactions between the vinylphosphonate and the MID domain of Ago2. Molecular modeling studies explain the position- and conformation-dependent RNAi-mediated gene silencing activity of 2′-F-NMC. Finally, the 5′-triphosphate of 2′-F-NMC is not a substrate for mitochondrial RNA and DNA polymerases, indicating that metabolites should not be toxic. 相似文献
246.
Balkrishen Bhat Guity Balow Andrei Guzaev P. Dan Cook Muthiah Manoharan 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1471-1472
Abstract A novel synthesis of the nucleoside-folic acid conjugates has been accomplished. This approach allowed us to synthesize several analogs, which were converted to phosphoramidites and successfully incorporated into therapeutically active antisense oligonucleotides. 相似文献
247.
Plasmonics - This study presents an in situ growth technique to develop highly sensitive plasmonic fiber optic sensors with an excellent control over the plasmonic properties of gold (AuNPs) and... 相似文献