2007
DOI: 10.1002/ejoc.200600747
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Solid‐Phase Synthesis of Acid‐Sensitive N‐(2‐Aminoethyl)glycine‐PNA Oligomers by the Fmoc/Bhoc Strategy

Abstract: In the context of investigation of nucleic acid‐mediated excess electron transfer, a bis‐functionalized (2‐aminoethyl)glycine‐PNA modified with a flavin and an oxetane moiety was synthesized. The solid‐phase synthesis of the required PNA oligomer was especially intriguing because of the high acid sensitivity of the oxetane moiety, so the Fmoc/Bhoc strategy was adapted to the mild cleavage conditions of the Sieberamide resin. Along with smooth oligomerization conditions, the syntheses of oxetane‐ and flavin‐fun… Show more

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Cited by 15 publications
(12 citation statements)
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“…[12] This chromophore was attached to an Fmoc-protected N-(2aminoethyl)glycine building block that is easily incorporated into PNA oligomers by standard solid-phase peptide synthesis (for details of the synthesis, see the Supporting Information). [13] We used a partially self-complementary DNA oligonucleotide containing a single interstrand crosslink as the substrate for the repair experiments (Scheme 2). It was prepared by irradiating 5'-d(GCCTAGGCAGGCAAGC-GAC) in the presence of AMT, [14] a commonly used psoralen derivative, in neutral Tris-HCl buffer (50 mm, 10 mm MgCl 2 , 100 mm NaCl, pH 7.5) at (340 AE 10) nm for 7 h at a constant temperature of 4 8C.…”
mentioning
confidence: 99%
“…[12] This chromophore was attached to an Fmoc-protected N-(2aminoethyl)glycine building block that is easily incorporated into PNA oligomers by standard solid-phase peptide synthesis (for details of the synthesis, see the Supporting Information). [13] We used a partially self-complementary DNA oligonucleotide containing a single interstrand crosslink as the substrate for the repair experiments (Scheme 2). It was prepared by irradiating 5'-d(GCCTAGGCAGGCAAGC-GAC) in the presence of AMT, [14] a commonly used psoralen derivative, in neutral Tris-HCl buffer (50 mm, 10 mm MgCl 2 , 100 mm NaCl, pH 7.5) at (340 AE 10) nm for 7 h at a constant temperature of 4 8C.…”
mentioning
confidence: 99%
“…PNA‐Oligomere wurden per Festphasen‐Peptidsynthese in guten Ausbeuten hergestellt11 und mithilfe von HPLC gereinigt. Vor der Hybridisierung wurden die PNA‐Derivate jeweils entweder thermisch (80 °C, 1 h) oder durch Belichtung (360 nm) mit dem trans ‐ bzw.…”
Section: Methodsunclassified
“…[12] Der Chromophor wurde in einen Fmoc-Aminoethylglycin-Baustein eingebracht und durch Festphasensynthese in PNA-Oligomere eingebaut (siehe Hintergrundinformationen). [13] Als Substrat für die Reparatur verwendeten wir ein partiell selbstpaarendes DNA-Oligomer, das eine einzelne Quervernetzung enthielt (Schema 2). Dieses wurde durch Belichten [(340 AE 10) nm, 7 h] von 5'-d(GCCTAGGCAGG-CAAGCGAC) in neutralem Tris-HCl-Puffer (50 mm, 10 mm MgCl 2 , 100 mm NaCl, pH 7.5) bei konstanter Temperatur (4 8C) in Gegenwart des Psoralenderivats AMT [14] erzeugt.…”
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