Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

Tímár, Zoltán; Kovács, Lajos; Kovács, George L.; Schmél, Zoltán

doi:10.1039/a907832k

Cited by 41 publications

(44 citation statements)

References 21 publications

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“…Initial attempts using acidic conditions were found to be unsuccessful, leading to either no reaction or to ferrocenylmethyl decomposition and indicated that the introduction of a ferrocenyl PNA monomer into a PNA sequence by automation and the subsequent cleavage from the resin is a real chemical challenge. While the ferrocenyl PNA monomer 2 is unsuitable for use in PNA synthesis that applies the XAL/PAL resin [21], these limitations may be overcome by using Fmoc/N-acyl protected PNA monomers [35,36] and highly cross-linked polystyrene beads functionalised with a glycine moiety as the solid support, as reported by Metzler-Nolte et al [9] This approach allows basic conditions (ethanolic ammonia) to be used to cleave the PNA from the resin.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a ferrocenyl uracil PNA monomer for insertion into PNA sequences

Gasser

Spiccia

2008

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

Synthesis of a ferrocenyl uracil PNA monomer for insertion into PNA sequences

Gasser

Spiccia

2008

Journal of Organometallic Chemistry

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“…15,21,46 All solution-phase NMR spectra were recorded using a Bruker Avance DRX 500 spectrometer operating at frequencies of 500. GHSQC and GSQMBC spectra were measured in the phase-sensitive mode (processed using the echo-antiecho protocol 47 -49 ) and with magnetic field gradients.…”

Section: Methodsmentioning

confidence: 99%

“…Simple empirical rules based on the differences in the chemical shift of some diagnostic 13 C signals have recently been found. 21 Nonetheless, a study of protons and carbons conveys only indirect information about the nitrogen backbone, which is certainly the most sensitive to the pattern of N 9 /N 7 -substitution.…”

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confidence: 99%

N⁷‐ and N⁹‐substituted purine derivatives: a ¹⁵N NMR study

Marek

Brus

Toušek

et al. 2002

Magnetic Reson in Chemistry

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The15 N NMR chemical shifts of N 7 -and N 9 -substituted purine derivatives were investigated systematically at the natural abundance level of the 15 N isotope. The NMR chemical shifts were determined and assigned using GSQMBC, GHMBC, GHMQC and GHSQC experiments in solution.15 N cross-polarization magic angle spinning data were recorded for selected compounds in order to study the principal values of the 15 N chemical shifts. Geometric parameters obtained by using RHF/6-31G * * and single-crystal x-ray structural analysis were used to calculate the chemical-shielding constants (GIAO and IGLO) which were then used to assign the nitrogen resonances observed in the solid-state NMR spectra and to determine the orientation of the principal components of the shift tensors.

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“…This technique has been used to identify histidine tautomers, [19] but we are aware of only one case, in which it was used to differentiate guanine isomers. [20] Scheme 3. Solid-phase assembly and deprotection of pyrr 2 Compounds 1-3 were assembled as in standard solidphase peptide synthesis by using a set of base-labile permanent protecting groups and acid-labile Boc temporary protecting groups (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%