82535-83-9Relevant academic research and scientific papers
Synthesis of a Thiophospho Analogue of Platelet Activating Factor (RS)- and (S)-1-Hexadecyl-2-acetylglycero-3-thiophosphocoline
Lamant, Valerie,Chap, Hugues,Klaebe, Alain,Perie, Jean J.,Willson, Michele
, p. 1608 - 1609 (1987)
A sequence for synthesis of the title compound from chloro(di-isopropylamino)methoxyphosphine is reported.
Catalytic synthesis of enantiopure mixed diacylglycerols-synthesis of a major M. tuberculosis phospholipid and platelet activating factor
Fodran, Peter,Minnaard, Adriaan J.
supporting information, 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.
Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
Stamatov, Stephan D.,Stawinski, Jacek
, p. 3787 - 3800 (2008/10/09)
A trifluoroacetate-catalyzed opening of the oxirane ring of glycidyl derivatives bearing allylic acyl or alkyl functionalities with trifluoroacetic anhydride (TFAA), provides an efficient entry to configurationally homogeneous 1(3)-acyl- or 1(3)-O-alkyl-sn-glycerols. Selective introduction of tert-butyldimethylsilyl- (TBDMS), or triisopropylsilyl- (TIPS) transient protections at the terminal sites within these key intermediates secures 1(3)-acyl- or 1(3)-O-alkyl-3(1)-O-TBDMS (or TIPS)-sn-glycerols as general bifunctional precursors to 1,2(2,3)-diacyl-, 1(3)-O-alkyl-2-acyl- and 1,3-diacyl-sn-glycerols and hence triester isosters. Incorporation of a requisite acyl residue at the central carbon of the silylated synthons with a subsequent Et3N·3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment at the stereogenic C2-centre of the monosilylated glycerides; (ii) replacement of the silyl moiety by a short- or long-chain carboxylic acid residue by means of the acylating agent: tetra-n-butylammonium bromide (TBABr)-carboxylic acid anhydride (CAA)-trimethylsilyl bromide (TMSBr); and (iii) removal of the trichloroacetyl replacement, provides pure 1,3-diacyl-sn-glycerols. The TBABr-CAA-TMSBr reagent system allows also a one-step conversion of 1,2-diacylglycerol silyl ethers into homochiral triglycerides with predefined asymmetry and degree of unsaturation. These compounds can also be accessed via a two-step one-pot approach where the trichloroacetyl derivatives of 1,2(2,3)- or 1,3-diacyl-sn-glycerols serve as triester building blocks for establishing the third ester bond at preselected C3(1)- or C2-positions within the glycerol skeleton at the very last synthetic stage. In all instances, the target compounds were produced under mild conditions, in high enantiomeric purity, and in practically quantitative yields. The Royal Society of Chemistry 2007.
A phosphatidylinositol 3,4,5-trisphosphate analogue with low serum protein-binding affinity
Wang, Da-Sheng,Hsu, Ao-Lin,Chen, Ching-Shih
, p. 133 - 139 (2007/10/03)
Phosphatidylinositol 3,4,5-trisphosphate (PIP3) plays an important role in the regulation of diverse physiological functions. Recent evidence indicates that PIP3 is cell permeant, and can be added exogenously to modulate cellular responses. However, like many other phospholipids, PIP3 binds serum proteins with high affinity, resulting in rapid deactivation of this lipid second messenger. Our study indicates that bovine serum albumin (BSA) at concentrations as low as 10 μg/mL abrogated the biological activity of dipalmitoyl-PIP3. This nonspecific interaction with serum proteins hampers the use of PIP3 in biological studies where serum is needed. We report here an ether-linked PIP3 analogue, 1-O-(1-O-hexadecyl-2-O-methyl-sn-glycero-3-phosphoryl)-myoinositol 3,4,5-trisphosphate (C16Me-PIP3), which displays low serum protein-binding affinity while retaining the biological function of PIP3. The affinity of C16Me-PIP3 with BSA was two orders of magnitude lower than that of its dipalmitoyl-counterpart. Biochemical data indicate that C16Me-PIP3 was able to stimulate Ca2+ influx in T cells in the presence of moderate levels (up to 1 mg/mL) of BSA. Thus, C16Me-PIP3 may provide a useful tool to study the physiological function of phosphoinositide (PI) 3-kinase in vivo.
