1487-50-9Relevant academic research and scientific papers
H-Phosphonate Synthesis and Biological Evaluation of an Immunomodulatory Phosphoglycolipid from Thermophilic Bacteria
Gan, Chin Heng,Hua, Kuo-Feng,Lam, Yulin,Li, Lan-Hui,Peng, Yi-Jen,Wei, Chih-Feng,Wijaya, Hadhi,Wu, Shih-Hsiung
supporting information, (2020/04/02)
The synthesis of a library of bacterial phosphoglycolipid, PGL-1, is described. Key features of the synthesis include regioselective esterification of the primary alcohol of the diacylglycerol moiety and an H-phosphonate method to install the phosphate in PGL-1 in comparison with earlier reported procedures. A representative set of PGL-1 analogues was prepared and evaluated for their biological activities. Results showed that the immunological activity of PGL-1 is dependent on the chain lengths of the fatty acids.
Synthesis of enantiopure ABC-type triacylglycerols
Gudmundsson, Haraldur G.,Linderborg, Kaisa M.,Kallio, Heikki,Yang, Baoru,Haraldsson, Gudmundur G.
, (2019/12/26)
The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils.
Total synthesis and mass spectrometric analysis of a: Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid
Burugupalli, Satvika,Richardson, Mark B.,Williams, Spencer J.
, p. 7422 - 7429 (2017/09/25)
We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The approach features a two-step synthesis of (R)-tuberculostearic acid, involving an (S)-citronellyl bromide linchpin, and the pho
Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis
Ter Horst, Bjorn,Seshadri, Chetan,Sweet, Lindsay,Young, David C.,Feringa, Ben L.,Moody, D. Branch,Minnaard, Adriaan J.
scheme or table, p. 1017 - 1022 (2010/09/14)
A glycerophospholipid (1-O-tuberculostearoyl-2-O-palmitoyl-sn-glycero-3- phosphoethanolamine) from Mycobacterium tuberculosis was isolated from the reference strain H37Rv. The molecular structure of this tuberculostearoyl [(R)-10-methyloctadecyl] and palm
Synthesis and structure of phosphatidylinositol dimannoside
Dyer, Blake S.,Jones, Jeremy D.,Ainge, Gary D.,Denis, Michel,Larsen, David S.,Painter, Gavin F.
, p. 3282 - 3288 (2008/02/04)
(Chemical Equation Presented) (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (5)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl) phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.
Synthesis of a small library of mixed-acid phospholipids from D-mannitol as a homochiral starting material
Xia, Jie,Hui, Yong-Zheng
, p. 1659 - 1663 (2007/10/03)
Synthesis of a series of mixed-acid phospholipids containing a polyunsaturated fatty acid using a newly protecting strategy are described. Thus, benzyl and methyl α-(2,4-dinitrophenyl)acetic acid which were respectively removed by BCl3 and 354 nm light are used as protecting groups.
ω-Mercapto analogs of naturally occurring lipids
Ohlsson, Joergen,Magnusson, Goeran
, p. 2011 - 2014 (2007/10/03)
Analogs of natural lipids, where one of the alkyl chains carries a terminal thiol functionality, were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives, respectively, thus creating lipid mimics suitable for anchoring to e.g. gold surfaces.
General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-glycerols
Martin, Stephen F.,Josey, John A.,Wong, Yue-Ling,Dean, Daniel W.
, p. 4805 - 4820 (2007/10/02)
An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof.The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP).A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation; this procedure is exemplified by the preparation of 10a,b.The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields.Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38.Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33.This phosphite coupling procedure was modified to assemble phospholipids bearing polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26.The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues.For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48.Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates may be prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.
