13143-92-5

Basic information

• Product Name: Methyl 2-O,3-O-dibenzoyl-4-O-(p-tolylsulfonyl)-β-L-arabinopyranoside
• Synonyms: Methyl 2-O,3-O-dibenzoyl-4-O-(p-tolylsulfonyl)-β-L-arabinopyranoside
• CAS NO: 13143-92-5
• Molecular Formula: C₂₇H₂₆O₉S
• Molecular Weight: 526.5549
• Mol File: 13143-92-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 660.4°Cat760mmHg
• Flash Point: 353.2°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 2.6E-17mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: Methyl 2-O,3-O-dibenzoyl-4-O-(p-tolylsulfonyl)-β-L-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-O,3-O-dibenzoyl-4-O-(p-tolylsulfonyl)-β-L-arabinopyranoside(13143-92-5)
• EPA Substance Registry System: Methyl 2-O,3-O-dibenzoyl-4-O-(p-tolylsulfonyl)-β-L-arabinopyranoside(13143-92-5)

Safety Data

• Hazardous Substances Data: 13143-92-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H26O9S/c1-18-13-15-21(16-14-18)37(30,31)36-22-17-33-27(32-2)24(35-26(29)20-11-7-4-8-12-20)23(22)34-25(28)19-9-5-3-6-10-19/h3-16,22-24,27H,17H2,1-2H3

Upstream product

• 29709-46-4 methyl 4-O-p-tolylsulfonyl-β-L-arabinopyranoside 
• 98-88-4 benzoyl chloride 
• 87-72-9 L-(+)-arabinose 
• 13143-91-4 methyl 2,3-di-O-benzoyl-β-L-arabinopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 91-09-8 methyl β-L-arabinopyranoside 
• 5328-37-0 L-arabinose 

Relevant articles and documents

Synthesis and structural insights into the binding mode of the albomycin δ1 core and its analogues in complex with their target aminoacyl-tRNA synthetase

Despite of proven efficacy and well tolerability, albomycin is not used clinically due to scarcity of material. Several attempts have been made to increase the production of albomycin by chemical or biochemical methods. In the current study, we have synthesized the active moiety of albomycin δ1 and investigated its binding mode to its molecular target seryl-trna synthetase (SerRS). In addition, isoleucyl and aspartyl congeners were prepared to investigate whether the albomycin scaffold can be extrapolated to target other aminoacyl-tRNA synthetases (aaRSs) from both class I and class II aaRSs, respectively. The synthesized analogues were evaluated for their ability to inhibit the corresponding aaRSs by an in vitro aminoacylation experiment using purified enzymes. It was observed that the diastereomer having the 5′S, 6′R-configuration (nucleoside numbering) as observed in the crystal structure, exhibits excellent inhibitory activity in contrast to poor activity of its companion 5′R,6′S-diasteromer obtained as byproduct during synthesis. Moreover, the albomycin core scaffold seems well tolerated for class II aaRSs inhibition compared with class I aaRSs. To understand this bias, we studied X-ray crystal structures of SerRS in complex with the albomycin δ1 core structure 14a, and AspRS in complex with compound 16a. Structural analysis clearly showed that diastereomer selectivity is attributed to the steric restraints of the active site of SerRS and AspRS.

Pyrrolidine sugars. Synthesis of 9-(4-acetamido-4-deoxy-beta-D-xylofuranosyl)adenine and other derivatives of 4-amino-4-deoxy-D-xylose.

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