Polyaza Crown Ethers as Non‐Nucleosidic Building Blocks in DNA Conjugates: Synthesis and Remarkable Stabilization of dsDNA

Rohr, Katja; Vogel, Stefan

doi:10.1002/cbic.200500392

Cited by 26 publications

(25 citation statements)

References 36 publications

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“…These azacrown derivatives possess varied hydrophobic segments in two aza-N positions. 32 The duplexes formed from such compounds exhibited tolerable stability.…”

Section: Brush-type Aonsmentioning

confidence: 99%

Nucleic acid amphiphiles: synthesis and self-assembled nanostructures

2011

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This review provides an overview of a relatively new class of bio-conjugates, DNA amphiphiles, which consist of oligonucleotides covalently bonded to synthetic hydrophobic units. The reader will find the basic principles for the structural design and preparation methods of the materials. Moreover, the self-assembly into superstructures of higher order will be highlighted. Finally, some potential applications will be described.

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“…These azacrown derivatives possess varied hydrophobic segments in two aza-N positions. 32 The duplexes formed from such compounds exhibited tolerable stability.…”

Section: Brush-type Aonsmentioning

confidence: 99%

Nucleic acid amphiphiles: synthesis and self-assembled nanostructures

2011

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“…Herein, we report on an improved synthetic strategy that allows for later-stage lipid anchor functionalization. The syntheses of benzylated diamine 1 and dialdehyde 3 have been described previously 37 . Hence, starting from 1 (see Fig.…”

Section: Resultsmentioning

confidence: 99%

Lipidated Polyaza Crown Ethers as Membrane Anchors for DNA-Controlled Content Mixing between Liposomes

Löffler

Hansen

Ries

et al. 2019

Sci Rep

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The ability to manipulate and fuse nano-compartmentalized volumes addresses a demand for spatiotemporal control in the field of synthetic biology, for example in the bottom-up construction of (bio)chemical nanoreactors and for the interrogation of enzymatic reactions in confined space. Herein, we mix entrapped sub-attoliter volumes of liposomes (~135 nm diameter) via lipid bilayer fusion, facilitated by the hybridization of membrane-anchored lipidated oligonucleotides. We report on an improved synthesis of the membrane-anchor phosphoramidites that allows for a flexible choice of lipophilic moiety. Lipid-nucleic acid conjugates (LiNAs) with and without triethylene glycol spacers between anchor and the 17 nt binding sequence were synthesized and their fusogenic potential evaluated. A fluorescence-based content mixing assay was employed for kinetic monitoring of fusion of the bulk liposome populations at different temperatures. Data obtained at 50 °C indicated a quantitative conversion of the limiting liposome population into fused liposomes and an unprecedently high initial fusion rate was observed. For most conditions and designs only low leakage during fusion was observed. These results consolidate LiNA-mediated membrane fusion as a robust platform for programming compartmentalized chemical and enzymatic reactions.

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“…One is by reacting lauroyl chloride with DGA in the presence of magnesium oxide [55,56] as shown in Eq. (1).…”

Section: Synthesismentioning

confidence: 99%

Synthesis of N‐(3‐Oxapropanoxyl)dodecanamide and its Application in Surfactant‐Polymer Flooding

Cui

Song

et al. 2010

J Surfact & Detergents

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Alkali-surfactant-polymer (ASP) flooding has been considered to be one of the useful tertiary oil recovery techniques. However, field tests in China have revealed that serious side effects may occur due to using alkali. Thus alkali-free SP flooding is more favorable in China. Unfortunately, surfactants effective in ASP flooding are usually ineffective in the absence of alkali and new surfactants need to be designed. In this paper N-(3-Oxapropanoxyl)dodecanamide as a pure compound and a mixture of homologues with narrow EO number distribution, synthesized by the reaction of lauroyl chloride with diglycolamine and addition of one ethylene oxide to coconut monoethanolamide respectively, are examined for their adaptability in SP flooding. It is found that, when mixed with betaines, both products can reduce Daqing crude oil/connate water interfacial tension to a magnitude of 10 -3 -10 -4 mNm -1 at 45°C in a wide surfactant concentration range, 0.01-0.5 wt%, and oil displacement tests using natural cores indicates that a tertiary oil recovery of 18.6 ± 0.4% OOIP can be achieved by SP flooding with the N-(3-Oxapropanoxyl)dodecanamide as the main surfactant without adding any alkaline agent and neutral electrolyte. N-(3-Oxapropanoxyl)dodecanamide, as a nonionic surfactant without a cloud point and producible industrially from renewable materials, is an ideal surfactant for SP flooding in the absence of an alkaline agent.

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Polyaza Crown Ethers as Non‐Nucleosidic Building Blocks in DNA Conjugates: Synthesis and Remarkable Stabilization of dsDNA

Cited by 26 publications

References 36 publications

Nucleic acid amphiphiles: synthesis and self-assembled nanostructures

Nucleic acid amphiphiles: synthesis and self-assembled nanostructures

Lipidated Polyaza Crown Ethers as Membrane Anchors for DNA-Controlled Content Mixing between Liposomes

Synthesis of N‐(3‐Oxapropanoxyl)dodecanamide and its Application in Surfactant‐Polymer Flooding

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