205191-96-4Relevant academic research and scientific papers
Probing the specificity of aminoglycoside-ribosomal RNA interactions with designed synthetic analogs
Alper, Phil B.,Hendrix, Martin,Sears, Pamela,Wong, Chi-Huey
, p. 1965 - 1978 (2007/10/03)
The binding of neomycin B and related aminoglycoside antibiotics to the prokaryotic ribosomal RNA decoding region has been investigated using a recently developed surface plasmon resonance assay. A number of naturally occurring aminoglycosides containing a neamine or neamine-like substructure bind specifically to a model of the site of the ribosomal decoding region RNA. This recognition event is the basis of the antibacterial activity of this class of compounds. A series of analogs was designed and synthesized to probe the role of neomycin ring IV (2,6-dideoxy-2,6-diamino-β-L- idopyranose). The binding results indicate that the positive charge presented on the idose ring is necessary for specific binding in vitro and cannot be replaced by amines attached via flexible linkers. However, the antibiotic activity (minimum inhibitory concentration) of the analog where ring IV is replaced with a diamine tail is the same as neomycin B in a liquid culture assay against Escherichia coli.
Synthesis of adenophostin analogues lacking the adenine moiety as novel potent IP3 receptor ligands: Some structural requirements for the significant activity of adenophostin a
Shuto, Satoshi,Tatani, Kazuya,Ueno, Yoshihito,Matsuda, Akira
, p. 8815 - 8824 (2007/10/03)
1-O-Tetrahydrofuranyl-α-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl acceptors selectively gave the corresponding α-glycosides, which were converted into the target compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1- O-tetrahydrofuranyl-α-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [3H] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.
Synthesis of methyl 2-O-allyl-(and 3-O-allyl-)5-O-benzyl-β-D-ribofuranoside
Desai,Gigg,Gigg
, p. 209 - 221 (2007/10/03)
D-Ribose was converted into methyl 5-O-benzyl-β-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-β-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-β-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O(prop-1-enyl)-β-D-ribofuranoside.
SYNTHESIS OF RIBOFURANOSIDES BY CATALYSIS WITH LEWIS ACIDS. GLYCOSIDATION VERSUS TRANSACETYLATION
Chiu-Machado, Ivan,Castro-Palomino, Julio C.,Madrazo-Alonso, Odalys,Lopetegui-Palacios, Carlos,Verez-Bencomo, Vicente
, p. 551 - 562 (2007/10/02)
Several ribofuranosyl derivatives bearing trichloroacetimidoyl or acetyl leaving groups in a Lewis acid promoted ribosylation reaction were prepared and used in an attempt to improve the yield and to avoid donor -> acceptor transacetylation.Trichloroaceti
