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Solid-Phase Synthesis of 5 '-O- N-(Acyl)sulfamoyl adenosine Derivatives

Itedale Namro Redwan ; Hanna Jacobson Ingemyr ; Thomas Ljungdahl (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Christopher P. Lawson (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Morten Grøtli
European Journal of Organic Chemistry (1434-193X). Vol. 2012 (2012), 19, p. 3665-3669.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: Medicinal chemistry, Synthetic methods, Solid-phase synthesis, Enzymes, Nucleosides, transfer-rna synthetase, mycobacterium-tuberculosis, siderophore, biosynthesis, pantothenate synthetase, analogs, inhibitors, adenylate, acid, antibiotics



Denna post skapades 2012-07-12.
CPL Pubid: 160426

 

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Institutioner (Chalmers)

Institutionen för kemi och molekylärbiologi (GU)
Institutionen för kemi- och bioteknik, Fysikalisk kemi (2005-2014)

Ämnesområden

Farmaceutisk synteskemi

Chalmers infrastruktur