21394-64-9Relevant articles and documents
N-acyl-O-phosphocholineserines: Structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease
Sidhu, Rohini,Mondjinou, Yawo,Qian, Mingxing,Song, Haowei,Kumar, Arun Babu,Hong, Xinying,Hsu, Fong-Fu,Dietzen, Dennis J.,Yanjanin, Nicole M.,Porter, Forbes D.,Berry-Kravis, Elizabeth,Vite, Charles H.,Gelb, Michael H.,Schaffer, Jean E.,Ory, Daniel S.,Jiang, Xuntian
, p. 1410 - 1424 (2019/08/30)
Niemann-Pick disease type C1 (NPC1) is a fatal, neurodegenerative, cholesterol storage disorder. With new therapeutics in clinical trials, there is an urgency to improve diagnostics and monitor therapeutic efficacy with biomarkers. In this study, we sought to define the structure of an unknown lipid biomarker for NPC1 with [M + H]+ ion at m/z 509.3351, previously designated as lysoSM-509. The structure of N-palmitoyl-O-phosphocholineserine (PPCS) was proposed for the lipid biomarker based on the results from mass spectrometric analyses and chemical derivatizations. As no commercial standard is available, authentic PPCS was chemically synthesized, and the structure was confirmed by comparison of endogenous and synthetic compounds as well as their derivatives using liquid chromatographytandem mass spectrometry (LC-MS/MS). PPCS is the most abundant species among N-acyl-O-phosphocholineserines (APCS), a class of lipids that have not been previously detected in biological samples. Further analysis demonstrated that all APCS species with acyl groups ranging from C14 to C24 were elevated in NPC1 plasma. PPCS is also elevated in both central and peripheral tissues of the NPC1 cat model. Identification of APCS structures provide an opportunity for broader exploration of the roles of these novel lipids in NPC1 disease pathology and diagnosis.-Sidhu, R., Y. Mondjinou, M. Qian, H. Song, A. B. Kumar, X. Hong, F-F. Hsu, D. J. Dietzen, N. M. Yanjanin, F. D. Porter, E. Berry- Kravis, C. H. Vite, M. H. Gelb, J. E. Schaffer, D. S. Ory, and X. Jiang. N-acyl-O-phosphocholineserines: structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease. J. Lipid Res. 2019. 60: 1410-1424.
New N-acylamino acids and derivatives from renewable fatty acids: Gelation of hydrocarbons and thermal properties
Duarte, Rodrigo Da Costa,Ongaratto, Renata,Piovesan, Luciana Almeida,De Lima, Vania Rodrigues,Soldi, Valdir,Merlo, Aloir Ant?nio,D'Oca, Marcelo G. Montes
supporting information; experimental part, p. 2454 - 2460 (2012/06/01)
This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of l-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of l-serine in forming good gels.
Chiral surfaces in micelles of enantiomeric N-palmitoyl- and N-stearoylserine
Shinitzky, Meir,Haimovitz, Rachel
, p. 12545 - 12549 (2007/10/02)
Circular dichroism (CD) spectra were recorded with micellar aggregates of a series of N-palmitoyl and N-stearoyl derivatives of amino acid enantiomers. N-Palmitoyl- and N-stearoyl-L- (or -D-) serine in the micelle form (10-4 M in aqueous 0.01 M KOH) exhibited a strong CD band centered at 213-215 nm which could be completely abolished by disintegrating the micelles in 50% ethanol. Analogous CD spectra of enantiomeric N-palmitoyl derivatives of tyrosine or proline did not display any exclusive band for the micellar form. The CD spectra of the enantiomeric N-palmitoyl- or N-stearoylserine micelles presumably originated from a repetitive arrangement of the amide planes on the micellar surface. Computer modeling suggested an alternating tilt of the amide planes associated with the formation of parallel spines of -NH?OC- intermolecular hydrogen bonds which cover the micellar surface. Each of such spines has a supramolecular chirality, which is presumably the origin of the observed CD band. The network of such chiral spines forms a unique chiral surface which may bear important implications for surface recognition and catalysis.
