2017
DOI: 10.1021/jacs.6b11997
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Conformationally Preorganized Diastereomeric Norbornane-Based Maltosides for Membrane Protein Study: Implications of Detergent Kink for Micellar Properties

Abstract: Detergents are essential tools for functional and structural studies of membrane proteins. However, conventional detergents are limited in their scope and utility, particularly for eukaryotic membrane proteins. Thus, there are major efforts to develop new amphipathic agents with enhanced properties. Here, a novel class of diastereomeric agents with a preorganized conformation, designated norbornane-based maltosides (NBMs), were prepared and evaluated for their ability to solubilize and stabilize membrane prote… Show more

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Cited by 47 publications
(52 citation statements)
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“…Therefore, they have a wide range of applications and development in food, cosmetic, pharmaceutical industries, and scientific research (de Foresta et al, ; Jastrzebska et al, ; Ni et al, ; Pillion et al, ; Raman et al, ; Rifkin et al, ; Santonicola et al, ; Weber and Benning, ; Zhang et al, ). They have been used in drug delivery (Ahmad et al, ), thermal stabilization (Ahmad et al, ), hydrolytic metabolism (Weber and Benning, ), salt tolerance (Zhang et al, ), formation of higher‐ordered structure (Jastrzebska et al, ), co‐immunoprecipitation (Lee et al, ), and structure analysis (Ni et al, ), as well as therapeutic adjuvants (Rifkin et al, ), permeation enhancers (Pillion et al, ), absorption enhancers (Gradauer et al, ), and membrane protein stabilizers against denaturation (Das et al, ; de Foresta et al, ; Jastrzebska et al, ; Klammt et al, ; Newby et al, ; Raman et al, ; Santonicola et al, ; Whorton and MacKinnon, ).…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Therefore, they have a wide range of applications and development in food, cosmetic, pharmaceutical industries, and scientific research (de Foresta et al, ; Jastrzebska et al, ; Ni et al, ; Pillion et al, ; Raman et al, ; Rifkin et al, ; Santonicola et al, ; Weber and Benning, ; Zhang et al, ). They have been used in drug delivery (Ahmad et al, ), thermal stabilization (Ahmad et al, ), hydrolytic metabolism (Weber and Benning, ), salt tolerance (Zhang et al, ), formation of higher‐ordered structure (Jastrzebska et al, ), co‐immunoprecipitation (Lee et al, ), and structure analysis (Ni et al, ), as well as therapeutic adjuvants (Rifkin et al, ), permeation enhancers (Pillion et al, ), absorption enhancers (Gradauer et al, ), and membrane protein stabilizers against denaturation (Das et al, ; de Foresta et al, ; Jastrzebska et al, ; Klammt et al, ; Newby et al, ; Raman et al, ; Santonicola et al, ; Whorton and MacKinnon, ).…”
Section: Introductionmentioning
confidence: 99%
“…Weber and Benning, 1984;Zhang et al, 1996). They have been used in drug delivery (Ahmad et al, 2014), thermal stabilization (Ahmad et al, 2014), hydrolytic metabolism (Weber and Benning, 1984), salt tolerance (Zhang et al, 1996), formation of higher-ordered structure (Jastrzebska et al, 2006), co-immunoprecipitation (Lee et al, 2018), and structure analysis (Ni et al, 2011), as well as therapeutic adjuvants (Rifkin et al, 2011), permeation enhancers (Pillion et al, 2002), absorption enhancers (Gradauer et al, 2017), and membrane protein stabilizers against denaturation (Das et al, 2017;de Foresta et al, 2011;Jastrzebska et al, 2006;Klammt et al, 2012;Newby et al, 2009;Raman et al, 2006;Santonicola et al, 2008;Whorton and MacKinnon, 2013).…”
Section: Introductionmentioning
confidence: 99%
“…, acyloxonium ion), known as anchimeric assistance, all glycosidic bonds were expected to be β. 27 The stereochemistry of the glycosylated products could be readily confirmed by 1 H NMR spectra of the final amphiphiles dissolved in CD 3 OD. The proton attached to the anomeric carbon (C1) was coupled to the neighboring C2 proton with a vicinal coupling constant ( 3 J ) of 8.0 Hz as both protons are in the axial position.…”
Section: Resultsmentioning
confidence: 90%
“…As for β 2 AR, the receptor in MNG-3 retained ~60% ligand binding ability after a 5-day incubation at room temperature in a previous study. 27 Under the same conditions, the TPS-E10L-solubilized receptor retained >85% activity. In the case of MelB St , the transporter extracted by TPS-E7 was more responsive to galactoside binding than the protein obtained in MNG-3.…”
Section: Resultsmentioning
confidence: 92%
“…[24] Theaggregated material was then removed by centrifugation and the supernatant submitted to SDS-PAGEa nd Western blot analysis to quantify the remaining solubilized MPs.Afull experiment is displayed in Figure 2B and Dfor each protein fraction incubated with 8b, allowing the apparent melting temperatures, T m ,a tw hich 50 %ofBmrA or A 2A Rremains in solution (dotted lines), to be estimated. [9] This result positions DCODs at the forefront of the very small set of stabilizing detergents,s uch as LMNG, [15] FA3, [17] and the recently published norbornane-based maltosides (NBMs), [25] that are able to generate an increase in T m of more than one log unit. Aclear effect was observed with respect to the hydrophobic component, namely the larger,the better.Note that this gain in thermostability is equivalent to that obtained previously by introducing 17 mutations in am altose-binding protein-A 2A Rf usion protein with aC -terminal 96 residue truncation.…”
mentioning
confidence: 92%