112921-04-7

Basic information

• Product Name: 5'-O-(N-(alanyl)sulfamoyl)adenosine
• Synonyms: 5'-O-(N-(alanyl)sulfamoyl)adenosine
• CAS NO: 112921-04-7
• Molecular Formula: C₁₃H₁₉N₇O₇S
• Molecular Weight: 417.4
• Mol File: 112921-04-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.04g/cm³
• CAS DataBase Reference: 5'-O-(N-(alanyl)sulfamoyl)adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(N-(alanyl)sulfamoyl)adenosine(112921-04-7)
• EPA Substance Registry System: 5'-O-(N-(alanyl)sulfamoyl)adenosine(112921-04-7)

Safety Data

• Hazardous Substances Data: 112921-04-7(Hazardous Substances Data)

Upstream product

• 1341125-30-1 C₃₀H₅₅N₇O₉SSi₂ 
• 863238-53-3 2',3'-O-bis(tert-butyldimethylsilyl)-5'-O-(sulfamoyl)adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 112921-00-3 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate 
• 112921-03-6 2',3'-O-isopropylidene-5'-O-(N-(Boc-L-alanyl)sulfamoyl)adenosine 

Relevant articles and documents

Solid-phase synthesis of 5'-O-[N-(Acyl)sulfamoyl]adenosine derivatives

The solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosine derivatives is described. The use of a Rink amide polystyrene solid support together with an appropriately protected ribo-purine starting material allowed for the development of a highly reliable and practical route for the solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosines. The developed procedure enables the efficient parallel synthesis of the target compounds in high yields. These compounds are non-hydrolysable isosteres of acyl-adenylates, which play an important role in a range of different metabolic pathways such as ribosomal and non-ribosomal peptide synthesis, fatty acid oxidation or enzyme regulation; some adenylate-forming enzymes are potential drug targets.

Extended targeting potential and improved synthesis of Microcin C analogs as antibacterials

Microcin C (McC) (1) is a potent antibacterial compound produced by some Escherichia coli strains. McC functions through a Trojan-Horse mechanism: it is actively taken up inside a sensitive cell through the function of the YejABEF-transporter and then pro

Exploiting ligand conformation in selective inhibition of non-ribosomal peptide synthetase amino acid adenylation with designed macrocyclic small molecules

Macrocyclic aminoacyl-AMP analogs have been developed to inhibit non-ribosomal peptide synthetase amino acid adenylation domains selectively by mimicking a cisoid ligand binding conformation observed in crystal structures. In contrast, these macrocycles d

A FACILE SYNTHESYS OF ASCAMYCIN AND RELATED ANALOGUES

The nucleoside antibiotic ascamycin (2-chloro-5'-O-(N-(L-alanyl)sulfamoyl)adenosine (1)) has been synthesized by an improved procedure involving the direct condensation of 2-chloro-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine (3) with Boc-L-Ala-OSu in DMF and the presence of DBU, followed by removal of the protecting groups.A similar condensation of 3 with Boc-D-Ala-Osu and Boc-Gly-Osu, and subsequent deprotection, yielded the D-Ala and Gly analogues of 1, namely 2-chloro-5'-O-(N-(D-alanyl)sulfamoyl) and 2-chloro-5'-O-(N-(glycyl)sulfamoyl)adenosine (D-ascamycin (14) and (18)).Similar reactions of 2',3'-O-isopropylidene-5'-O-sulfamoyladenosine, (6) with the tree amino acid derivatives above mentioned provided the corresponding adenosine analogues 12,16, and 20.Several studies directed to demonstrate that the previous protection of the 6-NH2 group of the adenosine derivatives 3 and 6 is not necessary for the selective aminoacylation of the SO2NH2 group are also reported.