NMR-based conformational analysis of sphingomyelin in bicelles

Yamaguchi, Toshiyuki; Suzuki, Takashi; Yasuda, Tomokazu; Oishi, Tohru; Matsumori, Nobuaki; Murata, Michio

doi:10.1016/j.bmc.2011.11.001

Cited by 29 publications

(34 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In fact, the orientation of the SM amide ( Fig. 10 b), as deduced from the results presented here as well as a previously determined conformation of SM (15), seems suitable for forming the intermolecular hydrogen bonds between SM amides, although it is also possible to form intermolecular hydrogen bonds with the OH group of Chol. The hydrogen bonds thus formed restrict the wobbling of the SM amide and enhance its order.…”

Section: Discussionmentioning

confidence: 74%

“…These labeled SMs were synthesized by coupling 13 C-labeled stearic acids with 2-15 N-lyso-SM prepared using a modification of a previously reported procedure ( Fig. 2) (15,23). Briefly, starting from 15 N-L-serine, the formation of a Weireb amide followed by a substitution reaction with a vinyl Grignard reagent provided a vinyl ketone.…”

Section: Resultsmentioning

confidence: 99%

“…10 a shows the two possible orientations of the amide plane of the SM-Chol membrane according to the values listed in Table 3. A recent report revealed that SM forms bicelles with dihexanoylphosphocholine (15), and its partial conformation in bicelles was determined, indicating that the conformation around the amide is relatively stable based on coupling constants typical of anti-rotamers. Based on the conformation of SM, the orientation corresponding to a b of 31 (Fig.…”

Section: Calculations Of the Rotation-axis Angles And Order Parametermentioning

confidence: 99%

“…Fig. 5 shows the 13 C CP-MAS spectra of 1 0 -13 C-2-15 N-SM in hydrated bilayers with SIMPSON simulation spectra, which resulted in estimates for the d ┴ and d // values (Table 2), in conjunction with the anisotropic parameter, 15 N CSA values of the The possible errors were within 53 ppm. Magnitude of the C-N intramolecular dipole coupling of SM amides Next, to determine the rotational-axis direction and the molecular order parameter of SM amide in bilayers, we measured the intramolecular C-N dipole couplings of 1 0 -13 C-2-15 N-SM and 2 0 -13 C-2-15 N-SM using the C-N REDOR method (30).…”

Section: And 15 N Csa Of Sm Amidesmentioning

confidence: 99%

“…Recently, Yamaguchi et al (15) determined the partial conformation of an SM molecule in a membrane environment using bicelles as a raft model, revealing that its conformation is relatively stable and capable of forming intermolecular hydrogen bonds between amide groups. In addition, the comprehensive and unambiguous order profiles of the SM alkyl chains were recently determined using site-specifically deuterated SMs (16,17).…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Orientation and Order of the Amide Group of Sphingomyelin in Bilayers Determined by Solid-State NMR

Matsumori

Yamaguchi

Maeta

et al. 2015

Biophysical Journal

Self Cite

View full text Add to dashboard Cite

Sphingomyelin (SM) and cholesterol (Chol) are considered essential for the formation of lipid rafts; however, the types of molecular interactions involved in this process, such as intermolecular hydrogen bonding, are not well understood. Since, unlike other phospholipids, SM is characterized by the presence of an amide group, it is essential to determine the orientation of the amide and its order in the lipid bilayers to understand the nature of the hydrogen bonds in lipid rafts. For this study, 1'-(13)C-2-(15)N-labeled and 2'-(13)C-2-(15)N-labeled SMs were prepared, and the rotational-axis direction and order parameters of the SM amide in bilayers were determined based on (13)C and (15)N chemical-shift anisotropies and intramolecular (13)C-(15)N dipole coupling constants. Results revealed that the amide orientation was minimally affected by Chol, whereas the order was enhanced significantly in its presence. Thus, Chol likely promotes the formation of an intermolecular hydrogen-bond network involving the SM amide without significantly changing its orientation, providing a higher order to the SM amide. To our knowledge, this study offers new insight into the significance of the SM amide orientation with regard to molecular recognition in lipid rafts, and therefore provides a deeper understanding of the mechanism of their formation.

show abstract

Section: Discussionmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Calculations Of the Rotation-axis Angles And Order Parametermentioning

confidence: 99%

Section: And 15 N Csa Of Sm Amidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Orientation and Order of the Amide Group of Sphingomyelin in Bilayers Determined by Solid-State NMR

Matsumori

Yamaguchi

Maeta

et al. 2015

Biophysical Journal

Self Cite

View full text Add to dashboard Cite

show abstract

Bioactive Structure of Membrane Lipids and Natural Products Elucidated by a Chemistry‐Based Approach

Murata

Sugiyama

Matsuoka

et al. 2015

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Determining the bioactive structure of membrane lipids is a new concept, which aims to examine the functions of lipids with respect to their three-dimensional structures. As lipids are dynamic by nature, their "structure" does not refer solely to a static picture but also to the local and global motions of the lipid molecules. We consider that interactions with lipids, which are completely defined by their structures, are controlled by the chemical, functional, and conformational matching between lipids and between lipid and protein. In this review, we describe recent advances in understanding the bioactive structures of membrane lipids bound to proteins and related molecules, including some of our recent results. By examining recent works on lipid-raft-related molecules, lipid-protein interactions, and membrane-active natural products, we discuss current perspectives on membrane structural biology.

show abstract

Molecular substructure of the liquid-ordered phase formed by sphingomyelin and cholesterol: sphingomyelin clusters forming nano-subdomains are a characteristic feature

et al. 2022

View full text Add to dashboard Cite

NMR-based conformational analysis of sphingomyelin in bicelles

Cited by 29 publications

References 33 publications

Orientation and Order of the Amide Group of Sphingomyelin in Bilayers Determined by Solid-State NMR

Orientation and Order of the Amide Group of Sphingomyelin in Bilayers Determined by Solid-State NMR

Bioactive Structure of Membrane Lipids and Natural Products Elucidated by a Chemistry‐Based Approach

Molecular substructure of the liquid-ordered phase formed by sphingomyelin and cholesterol: sphingomyelin clusters forming nano-subdomains are a characteristic feature

Contact Info

Product

Resources

About