NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

Afri, Michal; Alexenberg, Carmit; Aped, Pinchas; Bodner, Efrat; Cohen, Sarit; Ejgenburg, Michal; Eliyahu, Shlomi; Gilinsky-Sharon, Pessia; Harel, Yifat; Naqqash, Miriam E.; Porat, Hani; Ranz, Ayala; Frimer, Aryeh A.

doi:10.1016/j.chemphyslip.2014.07.007

Cited by 8 publications

(15 citation statements)

References 59 publications

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“…The general procedure for the preparation of sonically intercalated DMPC liposomal suspensions for the NMR studies has been described in the companion paper (Afri et al, 2014). Generally speaking, the intercalant concentration within the liposomal solution is 0.05 M and the ketoPC:DMPC molar ratio is 1:4.…”

Section: Sonic Intercalation Of Compounds Into Dmpc Liposomal Solutionsmentioning

confidence: 99%

“…1, ketophospholipids 4 were prepared by coupling ketoacids 2 with lysoPC 3 according to the procedure of Menger et al (1989). Ketoacids 2 were prepared, in turn, from ketoesters 1 as described in the companion paper (Afri et al, 2014). To assist in assignment and detection, several derivatives were prepared which were 13 C-enriched in both carbonyls by coupling the lysoPC 3 with doubly labeled ketoacids 2.…”

Section: Sonic Intercalation Of Compounds Into Dmpc Liposomal Solutionsmentioning

confidence: 99%

“…Ketoesters 1 and ketoacids 2 were prepared as described in the companion paper (Afri et al, 2014). Following the Menger approach (Menger et al, 1989), the ketoacids were then coupled with 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylcholine (lysoPC 3), mediated by DCC and DMAP, to give the corresponding 1-palmitoyl-2-(n 00 -oxostearoyl)-sn-glycero-3-phosphatidylcholines 4 in yields of ca.…”

Section: General Synthesis Of Ketophospholipidsmentioning

confidence: 99%

“…In the companion paper (Afri et al, 2014), we outlined the synthesis of two homologous series of bifunctional molecules: ketoesters 1 and ketoacids 2 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…This led us to believe that the ester carbonyls of ketoPCs 4a-f would fall in the desired 51-45 kcal/mol region. Using the NMR method described briefly above and in more detail in the companion paper (Afri et al, 2014), we hoped to determine the E T (30) polarity sensed by the various ester and ketone carbonyls in these ketoPCs. Combining these qualitative polarity results with the quantitive angstrom distance between the ketone and the ester carbons should allow us to complete the preparation of the desired ruler.…”

Section: Introductionmentioning

confidence: 99%

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NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

Afri

Alexenberg

Aped

et al. 2014

Chemistry and Physics of Lipids

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Section: Sonic Intercalation Of Compounds Into Dmpc Liposomal Solutionsmentioning

confidence: 99%

Section: Sonic Intercalation Of Compounds Into Dmpc Liposomal Solutionsmentioning

confidence: 99%

Section: General Synthesis Of Ketophospholipidsmentioning

confidence: 99%

“…In the companion paper (Afri et al, 2014), we outlined the synthesis of two homologous series of bifunctional molecules: ketoesters 1 and ketoacids 2 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

Afri

Alexenberg

Aped

et al. 2014

Chemistry and Physics of Lipids

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Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

Schink

Spielvogel

Imhof

2020

Labelled Comp Radiopharmac

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13C‐labeled dicarboxylic acids HO213C‐(CH2)n‐13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28) have been synthesized as internal standards for LC‐MS and GC‐MS analysis of cutin and suberin monomer degradation by soil‐based microorganisms. Different synthetic strategies had to be applied depending on the chain length of the respective synthetic target and because of economic considerations. 13C‐labels were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding dicarboxylic acids. All new compounds are characterized by GC/MS, IR, and NMR methods as well as by elemental analysis.

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Transmembrane β‐peptide helices as molecular rulers at the membrane surface

Martin

Sharma

Enderlein

et al. 2021

Journal of Peptide Science

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β-Peptides are known to form 14-helices with high conformational rigidity, helical persistence length, and well-defined spacing and orientation regularity of amino acid side chains. Therefore, β-peptides are well suited to serve as backbone structures for molecular rulers. On the one hand, they can be functionalized in a site-specific manner with molecular probes or fluorophores, and on the other hand, the β-peptide helices can be recognized and anchored in a biological environment of interest. In this study, the β-peptide helices were anchored in lipid bilayer membranes, and the helices were elongated in the outer membrane environment. The distances of the covalently bound probes to the membrane surface were determined using grapheneinduced energy transfer (GIET) spectroscopy, a method based on the distancedependent quenching of a fluorescent molecule by a nearby single graphene sheet. As a proof of principle, the predicted distances were determined for two fluorophores bound to the membrane-anchored β-peptide molecular ruler.

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NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

Cited by 8 publications

References 59 publications

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

Transmembrane β‐peptide helices as molecular rulers at the membrane surface

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NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

Cited by 8 publications

References 59 publications

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids

Synthesis of 13C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO213C‐(CH2)n‐13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

Transmembrane β‐peptide helices as molecular rulers at the membrane surface

Contact Info

Product

Resources

About

Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)