Fig. 2: Syntheses of scyllo-inositol 1,2,3,5-tetrakisphosphate (1-p), dl-6-deoxy-6-hydroxymethyl-scyllo-inositol 1,2,4-trisphosphate (racemic 5-s) and dl−6-deoxy-6-phosphoryloxymethyl-scyllo-inositol 1,2,4-trisphosphate (racemic 5-p). | Nature Communications

Fig. 2: Syntheses of scyllo-inositol 1,2,3,5-tetrakisphosphate (1-p), dl-6-deoxy-6-hydroxymethyl-scyllo-inositol 1,2,4-trisphosphate (racemic 5-s) and dl−6-deoxy-6-phosphoryloxymethyl-scyllo-inositol 1,2,4-trisphosphate (racemic 5-p).

From: Substrate promiscuity of inositol 1,4,5-trisphosphate kinase driven by structurally-modified ligands and active site plasticity

Fig. 2

Reagents and conditions: (a) NaBH4/MeOH/THF, 89%; (b) i. 1 M HCl/MeOH 1:10, reflux; ii. conc. aqueous NH3, 68%; (c) i. (CEO)2PNPri2, 1H-tetrazole, CH2Cl2, ii. m-CPBA, –78 °C, 85%; (d) Na/liq NH3, –78 °C, 71%; (e) Me3NBH3, AlCl3, 4 Å sieves, THF, 0 °C, 23 h, 65%; (f) 1 M HCl/EtOH 1:2, reflux, 87%; (g) i. (BnO)2PNPri2, 1H-tetrazole, CH2Cl2, ii. m-CPBA, –78 °C, 85%; (h) Na/liq NH3, –78 °C, 71%; (i) 1 M HCl/EtOH 1:2, reflux, 71%; (j) i. (BnO)2PNPri2, 1H-tetrazole, CH2Cl2, ii. m-CPBA, –78 °C, 72%; (k) H2, Pd-C, MeOH, 40 p.s.i., 75%. Bn = benzyl, PMB = p-methoxybenzyl, CE = 2-cyanoethyl. All asymmetrical compounds are racemic.

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