Single-Chain β-<scp>d</scp>-Glycopyranosylamides of Unsaturated Fatty Acids: Self-Assembly Properties and Applications to Artificial Cell Development

Bhattacharya, Ahanjit; Brea, Roberto J.; Song, Jing-Jin; Bhattacharya, Rupak; Sinha, Sunil K.; Devaraj, Neal K.

doi:10.1021/acs.jpcb.9b01055

Cited by 21 publications

(28 citation statements)

References 29 publications

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“…We synthesized GOA (Fig. 1A) as previously described (26). When a thin film of GOA deposited on the walls of a glass vial is hydrated with a solution containing the nonionic detergent IGEPAL (Fig.…”

Section: Resultsmentioning

confidence: 99%

Lipid sponge droplets as programmable synthetic organelles

Bhattacharya

Niederholtmeyer

Podolsky

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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Living cells segregate molecules and reactions in various subcellular compartments known as organelles. Spatial organization is likely essential for expanding the biochemical functions of synthetic reaction systems, including artificial cells. Many studies have attempted to mimic organelle functions using lamellar membrane-bound vesicles. However, vesicles typically suffer from highly limited transport across the membranes and an inability to mimic the dense membrane networks typically found in organelles such as the endoplasmic reticulum. Here, we describe programmable synthetic organelles based on highly stable nonlamellar sponge phase droplets that spontaneously assemble from a single-chain galactolipid and nonionic detergents. Due to their nanoporous structure, lipid sponge droplets readily exchange materials with the surrounding environment. In addition, the sponge phase contains a dense network of lipid bilayers and nanometric aqueous channels, which allows different classes of molecules to partition based on their size, polarity, and specific binding motifs. The sequestration of biologically relevant macromolecules can be programmed by the addition of suitably functionalized amphiphiles to the droplets. We demonstrate that droplets can harbor functional soluble and transmembrane proteins, allowing for the colocalization and concentration of enzymes and substrates to enhance reaction rates. Droplets protect bound proteins from proteases, and these interactions can be engineered to be reversible and optically controlled. Our results show that lipid sponge droplets permit the facile integration of membrane-rich environments and self-assembling spatial organization with biochemical reaction systems.

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Section: Resultsmentioning

confidence: 99%

Lipid sponge droplets as programmable synthetic organelles

Bhattacharya

Niederholtmeyer

Podolsky

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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“…S7). Single chain galactolipids with shorter unsaturated fatty acid chains (25) such as GPOA and GMOA were also found to form droplets with the same class of non-ionic surfactants (SI Appendix, Fig. S7).…”

Section: Resultsmentioning

confidence: 97%

“…We synthesized N-oleoyl β-Dgalactopyranosylamine (GOA, Fig. 1A) as previously described (25). When a thin lipid film of GOA deposited on the walls of a glass vial is hydrated with a solution containing the non-ionic detergent IGEPAL (Fig.…”

Section: Resultsmentioning

confidence: 99%

Lipid Sponge Droplets as Programmable Synthetic Organelles

Bhattacharya

Niederholtmeyer

Podolsky

et al. 2020

Preprint

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performed the biochemical, chemical, and imaging experiments. A.B., R.B., J.S., and S.K.S performed and analyzed the data for X-ray scattering experiments. A.B., H.N., and N.K.D wrote the manuscript. AbstractLiving cells segregate molecules and reactions in various subcellular compartments known as organelles. Spatial organization is likely essential for expanding the biochemical functions of synthetic reaction systems, including artificial cells. Many studies have attempted to mimic organelle functions using lamellar membrane-bound vesicles. However, vesicles typically suffer from highly limited transport across the membranes and an inability to mimic the dense membrane networks typically found in organelles such as the endoplasmic reticulum. Here we describe programmable synthetic organelles based on highly stable nonlamellar sponge phase droplets that spontaneously assemble from a single-chain galactolipid and nonionic detergents. Due to their nanoporous structure, lipid sponge droplets readily exchange materials with the surrounding environment. In addition, the sponge phase contains a dense network of lipid bilayers and nanometric aqueous channels, which allows different classes of molecules to partition based on their size, polarity, and specific binding motifs. The sequestration of biologically relevant macromolecules can be programmed by the addition of suitably functionalized amphiphiles to the droplets. We demonstrate that droplets can harbor functional soluble and transmembrane proteins, allowing for the co-localization and concentration of enzymes and substrates to enhance reaction rates. Droplets protect bound proteins from proteases, and these interactions can be engineered to be reversible and optically controlled. Our results show that lipid sponge droplets permit the facile integration of membrane-rich environments and selfassembling spatial organization with biochemical reaction systems. Significance statementOrganelles spatially and temporally orchestrate biochemical reactions in a cell to a degree of precision that is still unattainable in synthetic reaction systems. Additionally, organelles such as the endoplasmic reticulum (ER) contain highly interconnected and dense membrane networks that provide large reaction spaces for both transmembrane and soluble enzymes. We present lipid sponge droplets to emulate the functions of organelles such as the ER. We demonstrate that lipid sponge droplets can be programmed to internally concentrate specific proteins, host and accelerate biochemical transformations, and to rapidly and reversibly sequester and release proteins to control enzymatic reactions. The self-assembled and programmable nature of lipid sponge droplets will facilitate the integration of complex functions for bottom up synthetic biology.

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“…In general, the structure-related function of glycan sequences is not well understood, and molecular dynamics simulations indicate that even subtle changes in carbohydrate stereochemistry can have profound effects. 63 Similarly, self-assembly of synthetic vesicles with glucopyranose-and galactopyranose-derived single-chain amphiphiles show that differences in carbohydrate stereochemistry can drastically influence membrane shape and bending, 64 yet the underlying physical principles that drive these differences have not been clearly elucidated.…”

Section: Discussionmentioning

confidence: 99%

Reprogramming sphingolipid glycosylation is required for endosymbiont persistence in Medicago truncatula

et al. 2021

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Reprogramming sphingolipid glycosylation is required for endosymbiont persistence in Medicago truncatula Highlights d Sphingolipid glycosyltransferases are differentially expressed in symbiotic tissues d MtGINT1 is expressed in cell types synthesizing perimicrobial membranes d MtGINT1 functions in N-acetyl glucosamine sphingolipid glycosylation in planta d Silencing MtGINT1 impairs nodulation and arbuscular mycorrhizal symbiosis

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Single-Chain β-d-Glycopyranosylamides of Unsaturated Fatty Acids: Self-Assembly Properties and Applications to Artificial Cell Development

Cited by 21 publications

References 29 publications

Lipid sponge droplets as programmable synthetic organelles

Lipid sponge droplets as programmable synthetic organelles

Lipid Sponge Droplets as Programmable Synthetic Organelles

Reprogramming sphingolipid glycosylation is required for endosymbiont persistence in Medicago truncatula

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