Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.
Identifieur interne : 001F48 ( PubMed/Checkpoint ); précédent : 001F47; suivant : 001F49Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.
Auteurs : Andrzej Grajkowski [États-Unis] ; Jacek Cie Lak ; Jon S. Kauffman ; Robert J. Duff ; Scott Norris ; Dar N I. Freedberg ; Serge L. BeaucageSource :
- Bioconjugate chemistry [ 1520-4812 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- Amides (chemistry), Base Sequence, DNA (chemistry), DNA (genetics), Dinucleoside Phosphates (chemistry), Glass (chemistry), Hot Temperature, Hydrogen-Ion Concentration, Oligonucleotides (chemistry), Oligonucleotides (genetics), Phosphates (chemistry), Phosphoramides, Phosphoric Acids (chemistry), Porosity.
- MESH :
- chemical , chemistry : Amides, DNA, Dinucleoside Phosphates, Oligonucleotides, Phosphates, Phosphoric Acids.
- chemical , genetics : DNA, Oligonucleotides.
- chemistry : Glass.
- Base Sequence, Hot Temperature, Hydrogen-Ion Concentration, Phosphoramides, Porosity.
Abstract
The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.
DOI: 10.1021/bc800189e
PubMed: 18646834
Affiliations:
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pubmed:18646834Le document en format XML
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<term>Dinucleoside Phosphates (chemistry)</term>
<term>Glass (chemistry)</term>
<term>Hot Temperature</term>
<term>Hydrogen-Ion Concentration</term>
<term>Oligonucleotides (chemistry)</term>
<term>Oligonucleotides (genetics)</term>
<term>Phosphates (chemistry)</term>
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<term>ADN (génétique)</term>
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<term>Concentration en ions d'hydrogène</term>
<term>Dinucléoside phosphates ()</term>
<term>Oligonucléotides ()</term>
<term>Oligonucléotides (génétique)</term>
<term>Phosphates ()</term>
<term>Phosphoramides</term>
<term>Porosité</term>
<term>Séquence nucléotidique</term>
<term>Température élevée</term>
<term>Verre ()</term>
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<term>Phosphates</term>
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<term>Acides phosphoriques</term>
<term>Amides</term>
<term>Concentration en ions d'hydrogène</term>
<term>Dinucléoside phosphates</term>
<term>Oligonucléotides</term>
<term>Phosphates</term>
<term>Phosphoramides</term>
<term>Porosité</term>
<term>Séquence nucléotidique</term>
<term>Température élevée</term>
<term>Verre</term>
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<front><div type="abstract" xml:lang="en">The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.</div>
</front>
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<Abstract><AbstractText>The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.</AbstractText>
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