(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Flavin conjugate 46. Flavin carboxylic acid 36 (120 mg, 0.34 mmol; prepared according to well-known methods (Frier, et al. (1997) J. Org. Chem. 62:3520-3528)), DMF (6 mL), EDC (126 mg, 0.66 mmol), HOBt (89 mg, 0.66 mmol), neamine derivative 24 (400 mg, 0.22 mmol), deprotected conjugate hydrochloride 46 (120 mg, 0.13 mmol, 60%): mp 200° C. dec; 1H NMR (400 MHz, D2O) δ 7.47 (s, 1 H, H Fl), 7.43 (s, 1 H, H Fl), 5.69 (d, J1′-2′=3.8 Hz, 1H, H1′), 4.41 (m, 1H, CH2-Fl), 3.88-3.94 (m, 2H, H3′, H4), 3.78-3.87 (m, 2H, CH2O, H5′), 3.52-3.63 (m, 3H, CH2O, H5, H6), 3.33-3.50 (m, 4H, H3, H2′, H6′, H4′), 3.17-3.28 (m, 2H, H6′, H1), 2.92 (t, J=6.9 Hz, 2H, CH2N), 2.32-2.36 (m, 4H, H2eq, CH3 Fl), 2.23 (s, 3H, CH3 Fl), 2.08 (t, 2H, J=7.2 Hz, CH2CO), 1.76 (ddd, J2ax-1=J2ax-3=J2eq-2ax=12.6 Hz, 1H, H2ax), 1.63-1.70 (m, 2H, CH2 chain), 1.45-1.53 (m, 2H, CH2 chain), 1.35-1.45 (m, 2H, CH2 chain), 1.18-1.33 (m, 4H, 2CH2 chain), 1.05-1.15 (m, 4H, 2CH2 chain); 13C NMR (50 MHz, D2O) δ 176.0 (CO), [160.7, 157.3, 150.3, 148.7, 138.7, 134.0, 133.5, 130.5, 130.1, 115.8] (1C Fl), 92.5 (C1′), [82.1, 72.9, 72.2, 71.8, 69.7, 67.8] (6CH nea, CH2O), [52.8, 49.4, 48.5] (3CH nea), 45.2 (CH2N Fl), [39.6, 38.6] (CH2N, C6′), 35.1 (CH2-CO), [28.6, 27.7, 27.4, 25.7, 25.4, 24.8, 24.5, 24.2] (7CH2, C2), 20.3, (CH3), 18.2 (CH3); LRMS (electrospray) m/z=782.4 [M+Na]+, 600.3 [5-modified deoxystreptamine+H]+; HRMS (electrospray) Calcd for C36H57N9O9Na [M+Na]+: 782.4176, found: 782.4178.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When xylostasin is subjected to methanolysis with 0.4N HCl in methanol at 22°C for 6 days, methyl D-xyloside and neamine are produced and, when xylostasin is hydrolyzed with 0.5N sulfuric acid at 90°C for 6 hours, D-xylose and neamine are detected in the hydrolyzate.