Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

Kim, Young‐Ah; Park, Myoung-Soon; Kim, Young Hwan; Han, Sang M.

doi:10.1016/s0040-4020(03)00282-5

Cited by 18 publications

(6 citation statements)

References 34 publications

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“…It is very difficult to isolate individual molecular species of PC with a defined FA composition from any natural source. It is also cumbersome to synthesize PC chemically with a specified FA composition because it involves multistep procedures (5,6). Hydrogenation of PC isolated from soybean lecithin requires drastic reaction conditions and yields stearic acid-rich PC along with trans FA.…”

mentioning

confidence: 99%

Lipase‐catalyzed preparation of palmitic and stearic acid‐rich phosphatidylcholine

Reddy

Vijeeta

Karuna

et al. 2005

J Americ Oil Chem Soc

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Saturated FA enhance the oxidative stability of phospholipids. In the present study phosphatidylcholine (PC) rich in palmitic and stearic acids was prepared using lipase-catalyzed transesterification from PC isolated from egg and soybean lecithins. Two different lipases, namely, Novozym 435 and Lipozyme TL IM, were used for the transesterification. The reaction conditions were optimized by varying the lipase dosage, molar ratio of PC to FA, and reaction period. Palmitic acid could be incorporated up to 58.6 and 57.1% using Lipozyme TL IM and 56 and 61% using Novozym 435 in egg and soybean PC from an initial content of 37.4 and 16.8%, respectively. Similarly, stearic acid incorporation was up to 44.7 and 46.3% using Lipozyme TL IM and 37.2 and 55.8% using Novozym 435 in egg and soybean PC from an initial content of 8.6 and 2.1%, respectively.

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confidence: 99%

Lipase‐catalyzed preparation of palmitic and stearic acid‐rich phosphatidylcholine

Reddy

Vijeeta

Karuna

et al. 2005

J Americ Oil Chem Soc

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“…First, the 1,3-diol of glycerol was protected as 1,3-benzylideneglycerol 1 by treatment with p-TsOH and benzaldehyde. 32,35 Succinic acid was coupled to 1 in the presence of N,N-dicyclohexyl carbodiimide (DCC) and 4-(dimethylamino) pyridinium 4-toluenesulfonate (DPTS); the product was then purified by column chromatography. The benzylidene acetal group of the core was subsequently removed by hydrogenolysis (20% (w/w) with Pd(OH) 2 /C at 50 psi H 2 in THF) to yield the tetrahydroxy G1-core 3 (76% yield).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Poly(glycerol-succinic acid)-dithiocarbamate and Poly(glycerol-succinic acid)-1,3,4-thiadiazole Dendrimers and Their Use as Anti-Wear Oil Additives

Kim¹,

Hoang²,

Kim³

et al. 2013

Bulletin of the Korean Chemical Society

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A series of poly(glycerol-succinic acid) dithiocarbamate and 1,3,4-thiadiazole dendrimers, which have potential as anti-wear oil additives, were synthesized. Their anti-wear properties in three different oils (100N, DB-51, and soybean) were evaluated using a four-ball wear tester. The results indicated that thiocarbamate dendrimers have moderate anti-wear properties in DB-51 oil, and 1,3,4-thiadiazole dendrimers exhibited good anti-wear properties in 100N and DB-51 oils. However, dithiocarbamate and 1,3,4-thiadiazole dendrimers were not effective anti-wear additives in soybean oil.

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“…The 2-O-acylglycerols are known to be isomerizable to 1-O-acylglycerols via acyl migration during extraction and separation [18] [19]. Because of this migratory aptitude, G-4 was not subjected to an extensive purification.…”

Section: -O-[(3r6s)-3-(acetyloxy)-6-hydroxyoctadecanoyl]glycerol) (1mentioning

confidence: 99%

Acylglycerols (=Glycerides) from the Glandular Trichome Exudate on the Leaves of Paulownia tomentosa

Asai

Hara

Kobayashi

et al. 2009

Helvetica Chimica Acta

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Chemical investigations of the glandular trichome exudates on the leaves of Paulownia tomentosa (Scrophulariaceae) led to the identification of the thirty acylglycerols (=glycerides) 1–30, including five known ones (2, 3, 6, 9, and 15) (Fig. 1). Spectroscopic analysis combined with GC/MS studies of the glycerides and the liberated fatty acids, in the form of trimethylsilyl ether derivatives and trimethylsilylated methyl esters, respectively, established that the constituents belonged to 1,3‐di‐O‐acetyl‐2‐O‐(fatty acyl)glycerols, 1‐O‐acetyl‐2‐O‐(fatty acyl)‐sn‐glycerols, and 2‐O‐(fatty acyl)glycerols, wherein the fatty acyl moiety was either an eicosanoyl or an octadecanoyl group bearing OH and/or AcO groups at the 3‐, 3,6‐, 3,7‐, 3,8‐, or 3,9‐positions. The 1‐O‐acetyl‐2‐O‐[(3R,6S)‐3‐(acetyloxy)‐6‐hydroxyeicosanoyl]‐sn‐glycerol (12; 20% of the total glycerides), 2‐O‐[(3R,8R)‐3,8‐bis(acetyloxy)eicosanoyl]glycerol (17; 14%), 2‐O‐[(3R,9R)‐3,9‐bis(acetyloxy)eicosanoyl]glycerol (18; 12%), and 2‐O‐[(3R)‐3‐(acetyloxy)eicosanoyl]glycerol (10; 12%) were relatively abundant constituents. The configurations of the stereogenic centers of the fatty acyl moieties were determined by 1H‐NMR analysis of the monoesters obtained from (R)‐ and (S)‐2‐(naphthalen‐2‐yl)‐2‐methoxyacetic acid ((R)‐ and (S)‐2NMAOH and the hydroxy‐substituted fatty acid methyl esters (Fig. 2). The configuration at C(2) of the glycerol moiety of the 1‐O‐acetyl‐2‐O‐(fatty acyl)glycerols was determined to be (2S) by chemical conversion of, e.g., G‐2 (=2/3 1 : 10) to (+)‐3‐O‐[tert‐butyl)diphenylsilyl]‐sn glycerol of known absolute configuration.

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Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

Cited by 18 publications

References 34 publications

Lipase‐catalyzed preparation of palmitic and stearic acid‐rich phosphatidylcholine

Lipase‐catalyzed preparation of palmitic and stearic acid‐rich phosphatidylcholine

Synthesis of Poly(glycerol-succinic acid)-dithiocarbamate and Poly(glycerol-succinic acid)-1,3,4-thiadiazole Dendrimers and Their Use as Anti-Wear Oil Additives

Acylglycerols (=Glycerides) from the Glandular Trichome Exudate on the Leaves of Paulownia tomentosa

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