133398-13-7Relevant academic research and scientific papers
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.
, p. 1017 - 1022 (2010)
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
α-Glucuronosyl and α-glucosyl diacylglycerides, natural killer T cell-activating lipids from bacteria and fungi
Burugupalli, Satvika,Almeida, Catarina F.,Smith, Dylan G. M.,Shah, Sayali,Patel, Onisha,Rossjohn, Jamie,Uldrich, Adam P.,Godfrey, Dale I.,Williams, Spencer J.
, p. 2161 - 2168 (2020/03/10)
Natural killer T cells express T cell receptors (TCRs) that recognize glycolipid antigens in association with the antigen-presenting molecule CD1d. Here, we report the concise chemical synthesis of a range of saturated and unsaturated α-glucosyl and α-glucuronosyl diacylglycerides of bacterial and fungal origins from allyl α-glucoside with Jacobsen kinetic resolution as a key step. These glycolipids are recognized by a classical type I NKT TCR that uses an invariant Vα14-Jα18 TCR α-chain, but also by an atypical NKT TCR that uses a different TCR α-chain (Vα10-Jα50). In both cases, recognition is sensitive to the lipid fine structure, and includes recognition of glycosyl diacylglycerides bearing branched (R- and S-tuberculostearic acid) and unsaturated (oleic and vaccenic) acids. The TCR footprints on CD1d loaded with a mycobacterial α-glucuronosyl diacylglyceride were assessed using mutant CD1d molecules and, while similar to that for α-GalCer recognition by a type I NKT TCR, were more sensitive to mutations when α-glucuronosyl diacylglyceride was the antigen. In summary, we provide an efficient approach for synthesis of a broad class of bacterial and fungal α-glycosyl diacylglyceride antigens and demonstrate that they can be recognised by TCRs derived from type I and atypical NKT cells.
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
Catalytic synthesis of enantiopure mixed diacylglycerols-synthesis of a major M. tuberculosis phospholipid and platelet activating factor
Fodran, Peter,Minnaard, Adriaan J.
, p. 6919 - 6928 (2013/10/08)
An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.
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.
A new short synthesis of 10R-tuberculostearic acid and its enantiomer
Roberts, Ieuan O.,Baird, Mark S.
, p. 111 - 117 (2007/10/03)
Tuberculostearic acid (10R-methyloctadecanoic acid) and its 10S-enantiomer were synthesised by a chiral pool strategy, in four steps from citronellyl bromide.
Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis
Liu, Xinyu,Stocker, Bridget L.,Seeberger, Peter H.
, p. 3638 - 3648 (2007/10/03)
The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudo
