Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis.
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Summary
The stereochemistry of HPA-12 was definitely determined to be 1R,3S, consistent with Berkeš's revised structure, and a large-scale synthetic method based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed.
- Type
- article
- Published
- 2013-05-23
- Cited by
- 32
- References
- 24
- OpenAlex
- https://openalex.org/W23701643
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:20681746
Keywords
Political science, Humanities, Philosophy
References
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- Sphingolipid signaling in metabolic disorders
- Catalytic enantioselective synthesis of a novel inhibitor of ceramide trafficking, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12)
- Molecular machinery for non-vesicular trafficking of ceramide
- Enantio- and diastereoselective, stereospecific mannich-type reactions in water.
- Host sphingolipid biosynthesis as a target for hepatitis C virus therapy
- Regulators of mitotic arrest and ceramide metabolism are determinants of sensitivity to paclitaxel and other chemotherapeutic drugs.
- CERT Mediates Intermembrane Transfer of Various Molecular Species of Ceramides*
- MicroRNAs in the Pineal Gland
- Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives.
- Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics
- Stereoselective synthesis of (−)-allosedamine and (1R,3R)-HPA-12 from β-p-toluenesulfonamido-γ,δ-unsaturated sulfoxide☆
- Use of high performance liquid chromatography-electrospray ionization-tandem mass spectrometry for the analysis of ceramide-1-phosphate levels[S]
- Decreased Ceramide Transport Protein (CERT) Function Alters Sphingomyelin Production following UVB Irradiation*
- Serine palmitoyltransferase, a key enzyme of sphingolipid metabolism.
- Catalytic, asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12.
- Crystal structures of the CERT START domain with inhibitors provide insights into the mechanism of ceramide transfer.
- Catalytic asymmetric mannich-type reactions activated by ZnF2 chiral diamine in aqueous media.
- The catalytic asymmetric Mannich-type reactions in aqueous media.
Cited by
- Facile synthesis of the CERT inhibitor HPA-12 and some novel derivatives.
- Trafficking of Acetyl‐C16‐Ceramide‐NBD with Long‐Term Stability and No Cytotoxicity into the Golgi Complex
- Ruthenium-catalyzed asymmetric N-demethylative rearrangement of isoxazolidines and its application in the asymmetric total syntheses of (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.
- BF3-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes.
- Identification of Novel CERT Ligands as Potential Ceramide Trafficking Inhibitors
- A novel inhibitor of ceramide trafficking from endoplasmic reticulum to the site of sphingomyelin synthesis.
- Development of a CERT START Domain–Ceramide HTRF Binding Assay and Application to Pharmacological Studies and Screening
- Co-evolution of sphingomyelin and the ceramide transport protein CERT.
- ABCB4 exports phosphatidylcholine in a sphingomyelin-dependent manner[S]
- A straightforward synthesis of the CERT inhibitor (1′R,3′S)-HPA-12
- The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.
- Stereoselective synthesis of 1,3-amino alcohols by the Pd-catalyzed cyclization of trichloroacetimidates.
- A biologically relevant ceramide fluorescent probe to assess the binding of potential ligands to the CERT transfer protein
- Synthesis of syn-1,3-aminoalcohols via a Ru-catalyzed N-demethylative rearrangement of isoxazolidines and its application in a three-step total synthesis of HPA-12.
- Asymmetric Synthesis and Binding Study of New Long-Chain HPA-12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT.
- Organocatalytic route to enantioselective synthesis of ceramide trafficking inhibitor HPA-12
- Conception, synthèse et évaluation de nouveaux inhibiteurs du transport de céramide : vers de nouveaux agents de sensibilisation des cellules cancéreuses chimiorésistantes
- Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
- A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12
- Synthesis of 1,3-Amino Alcohols by Hydroxy-Directed Aziridination and Aziridine Hydrosilylation.
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