| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - A Tetramethyl Rhodamine (Tamra) Phosphoramidite FacilitatesSolid-Phase-Supported Synthesis of 5‘-Tamra DNA
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - 5-Carboxy Tamra 1 was conjugated to 4-hydroxypiperidine with BOP and N-methylmorpholine,and the resulting 5-(N-pipyridyl-4-hydroxy)-Tamra carboxamide 2 was treated with 2-cyanoethyltetraisopropylphosphorodiamidite to give 5-[N-pipyridyl-4-O-(2-cyanoethyl diisopropylphosphoramidite)]-Tamra carboxamide 3. Solutions of 3 were coupled onto the 5‘-hydroxyl of solid-phase-supported DNA fragments with standard amidite coupling techniques. Cleavage and deprotectionwith aqueous tert-butylamine cocktail gave 5-Tamra-functionalized DNA as well as an additionalcompound without the Tamra chromophore. A mass spectrum of this product showed theincorporation of tert-butylamine. The extra product was completely suppressed by including a 5min acetylation step after coupling. A model study of 3 coupled onto thymidine-functionalized CPGshowed similar results. NMR and mass spectra of cleaved products confirmed the addition of tert-butylamine to the minor product. Coupling a Tamra active ester onto T CPG which was previouslycoupled with N-(4-methoxytrityl)piperidyl-4-O-(2-cyanoethyl diisopropylphosphoramidite) 4 producedthe same major Tamra-bearing product, which coeluted on reverse phase HPLC with the majorproduct generated with 3.
|
| article type
| |
| is part of this journal
| |
