Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides and Oligodipeptoids Tagged with Triazines as Recognition Elements

Mittapalli, Gopi Kumar; Reddy, Kongara Ravinder; Xiong, Hui; Munoz, Omar; Han, Baozhong; Riccardis, Francesco De; Krishnamurthy, Ramanarayanan; Eschenmoser, Albert

doi:10.1002/anie.200603207

Cited by 96 publications

(89 citation statements)

References 95 publications

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“…Janus-Neamine ligands (20)(21)(22)(23) were easily synthesized in a two-step process which implicates two consecutive thiol-disulfide exchange reactions. First, thiol-derivatized neamine monomers (Nea or Nea2) 11 were activated with 2,2'-dithiobis(5-nitropyridine) (DTNP) 24 under acidic conditions for 15 h under Ar atmosphere.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…First, thiol-derivatized neamine monomers (Nea or Nea2) 11 were activated with 2,2'-dithiobis(5-nitropyridine) (DTNP) 24 under acidic conditions for 15 h under Ar atmosphere. Then, the disulfide intermediates were reacted with the thiol-containing Janus-peptide monomers (18 or 19), which afforded the desired ligands (20)(21)(22)(23) after purification by reversed-phase HPLC (yields 21-53%). All the compounds were fully characterized by NMR (1D 1 H, COSY, TOCSY) and high-resolution ESI mass spectrometry.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…As shown in Scheme 3, the guanidinylated ligands (24)(25)(26)(27) were prepared by direct guanidinylation of their precursors (20)(21)(22)(23) following previously reported procedures. n=2 JanusB-Nea2 (23) JanusB-Nea2G4 (27) Scheme 3.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…Our next objective was to study the interaction of Janus-Neamine ligands (20)(21)(22)(23) and their guanidinylated derivatives, Janus-Guanidinoneamine (24)(25)(26)(27), with Tau RNA, and in particular to evaluate their ability to stabilize Tau RNA. Besides wt we choose two of the mutated sequences associated with the development of tauopathies, +3 and +16.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…9, 167.7, 166.0, 163.9, 154.4, 149.6, 100.3, 49.0, 30.7, 24.4 Solid-phase synthesis of Janus-peptide derivatives (18 and 19). Synthesis of Janus-Neamine ligands (20)(21)(22)(23).…”

Section: Ethyl 4-(4-amino-7-(bis(tert-butoxycarbonyl)amino)-2-oxopyrimentioning

confidence: 99%

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Synthesis of Janus Compounds for the Recognition of G-U Mismatched Nucleobase Pairs

Artigas

Marchán

2013

J. Org. Chem.

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The design and synthesis of two Janus-type heterocycles with capacity to simultaneously recognize guanine and uracyl in G-U mismatched pairs through complementary hydrogen bond pairing is described. Both compounds were conveniently functionalized with a carboxylic function and efficiently attached to a tripeptide sequence by using solid-phase methodologies. Ligands based on the derivatization of such Janus compounds with a small aminoglycoside, neamine, and its guanidinylated analogue have been synthesized, and their interaction with Tau RNA has been investigated by using several biophysical techniques, including UV-monitored melting curves, fluorescence titration experiments and 1 H NMR.The overall results indicated that Janus-neamine/guanidinoneamine showed some preference for the +3 mutated RNA sequence associated with the development of some tauopathies, although preliminary NMR studies have not confirmed binding to G-U pairs.Moreover, a good correlation has been found between the RNA binding affinity of such 2 Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.

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Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…9, 167.7, 166.0, 163.9, 154.4, 149.6, 100.3, 49.0, 30.7, 24.4 Solid-phase synthesis of Janus-peptide derivatives (18 and 19). Synthesis of Janus-Neamine ligands (20)(21)(22)(23).…”

Section: Ethyl 4-(4-amino-7-(bis(tert-butoxycarbonyl)amino)-2-oxopyrimentioning

confidence: 99%

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