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. 2010 May 3;5(5):682-6.
doi: 10.1002/cmdc.201000018.

Synthesis and properties of a photoactivatable analogue of psychosine (beta-Galactosylsphingosine)

Ravi S Lankalapalli  1 , Attila Baksa, Károly Liliom, Robert Bittman
Affiliations

Synthesis and properties of a photoactivatable analogue of psychosine (beta-Galactosylsphingosine)

Ravi S Lankalapalli et al. ChemMedChem. .
No abstract available

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Figures

Figure 1
Figure 1
Intracellular Ca2+ mobilization by 1 and psychosine in U937 human leukemia cells. a) Time course of Ca2+ mobilization by 1 (–––) and psychosine (—) measured in Ca2+-free buffer. Cells were loaded with Fluo-4 AM, washed, and the fluorescence intensity was recorded in a cuvette. The compounds were added to the cell suspensions at the time indicated by the arrow. For comparison, the response to ATP (–•–•) by endogenous purinergic receptors was also examined. b) The average response of U937 cells to 1 (30 μm) and psychosine (10 μm) at 60 s after addition of the compounds. Fluo-4 fluorescence intensities were read from similar traces shown in panel a. Data represent the mean ±SEM of three independent determinations.
Scheme 1
Scheme 1
Synthesis of pentenyl-β-d-galactosides 7 and 8. Reagents and conditions: a) CH2=CHMgBr, THF, −78°C, 2 h, 62%; b) tBuC(O)Cl, cat DMAP/Et3N, CH2Cl2, 0°C→RT, 93 %; c) 1. HCl (2m)/EtOH (1:4), 70–80 °C, 3 h; 2. TfN3 in CH2Cl2, K2CO3, CuSO4·H2O (0.01 equiv), MeOH, H2O, 5 h, 70% (two steps); d) BF3·Et2O, dry CH2Cl2, 4 Å MS, RT, 4 h, 71%; e) 1. Ph3P, C6H6, H2O (1 drop), overnight; 2. (Boc)2O, Et3N, CH2Cl2, RT, overnight, 79% (two steps). Abbreviations: Piv, pivaloyl; DMAP, (4-dimethylamino)pyridine; Boc, tert-butyloxycarbonyl; TfN3, trifyl azide; MS, molecular sieves; (Boc)2O, di-tert-butyl dicarbonate.
Scheme 2
Scheme 2
Synthesis of psychosine analogue 1 by olefin metathesis. Reagents and conditions: a) 10-bromo-1-decene (4 equiv), Grubbs' second generation catalyst (0.3 equiv), CH2Cl2, reflux, 16 h, 63%; b) 4-hydroxybenzophenone, K2CO3, DMF, microwave, 120 °C, 1.5 h, 85 %; c) NaOMe in MeOH, THF, RT, 2 d, 90%; d) HCl (1m) in 90 % HOAc, CH2Cl2, RT, 35 min, 94%. Abbreviations: O-BP, 4-O-benzophenone.
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