Synthesis of enantiomerically pure phosphorothiolate assay substrate for phosphatidylinositol-specific phospholipase C

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 10, 1997, Pages 1235-1238

  Mihai, Cornelia ^a   Mataka, Jan ^a   Riddle, Suzette ^b   Tsai, Ming Daw ^b   Bruzik, Karol S ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INOSITOL DERIVATIVE; PHOSPHOLIPASE C;

ARTICLE; BACILLUS THURINGIENSIS; DRUG SYNTHESIS; ENANTIOMER; ENZYME ASSAY; ENZYME SUBSTRATE; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031579962     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00197-2     Document Type: Article

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25. 31P NMR spectra. The chirality at the phosphorus atom is removed during demethylation of the thioltriester 16.
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28. 1a: 1H NMR (400 MHz, CD3OD) δ 5.3 (m, 1H), 4.46 (dd, 1H), 4.23 (tr, 1H), 3.98 (ddd, 1H), 3.78 (m, 2H), 3.63 (m, 2H), 3.38 (m, 2H), 3.04 (dd, 2H), 2.32 (tr, 4H), 1.61 (m, 4H), 1.31 (m, 16H), 0.91 (tr, 6H); 31P NMR (CD3OD) δ 19.83 ppm; ESMS: m/z 601 (M+H+). 1b: ESMS: m/z 825 M+H+); other data were essentially identical to those of 1a, except for the integration of the hydrocarbon protons in the 1H NMR spectrum.
29. The substrate 1b could not be tested without detergent due to its insolubility in the aqueous phase. In contrast, the substrate 1a dispersed with HDPC displayed significant decrease of the cleavage rate following the initial few percent of conversion.
30. The Km value for the substrate 1a appears to be slightly smaller than that for vesicular dimirystoyl thiol analog (0.2 mM) reported recently.