UDP GlcNAc6N3 → UDP GlcNAc6NH2

HRID 928867Notes

Reaction equation

HRID 928867 reaction equation
[CH:1]1[C:7](=[O:8])[NH:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][O:15][P:16]([O:19][P:20]([OH:23])([OH:22])=[O:21])([OH:18])=[O:17])[C@@H:11]([OH:24])[C@H:10]2[OH:25])[CH:2]=1.[OH:26][CH:27]1[O:34][C@H:33]([CH2:35]ON=[N+]=[N-])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:28]1[NH:40][C:41]([CH3:43])=[O:42]>CO.O.[Pd]>[CH:1]1[C:7](=[O:8])[NH:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][O:15][P:16]([O:19][P:20]([OH:22])([OH:23])=[O:21])([OH:18])=[O:17])[C@@H:11]([OH:24])[C@H:10]2[OH:25])[CH:2]=1.[OH:26][CH:27]1[O:34][C@H:33]([CH2:35][NH2:3])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:28]1[NH:40][C:41]([CH3:43])=[O:42]

Participants

4

Reactant 1

HCID 131735066UDP GlcNAc6N3

Product 1

HCID 131735064UDP GlcNAc6NH2Yield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

UDP-GlcNAc6N3 (T5b-12 or F5-9) (100 mg, 0.16 mmol) was dissolved in MeOH—H2O (10 mL, 1:1, v/v) and 20 mg of Pd/C was added. The mixture was shaken under H2 gas (4 Bar) for 1 hr, filtered, and concentrated. The residue was purified by flash column chromatography (EtOAc:MeOH:H2O=3:2:1, by volume) to afford UDP-GlcNAc6NH2 F5-10 in 96% yield (93 mg). 1H NMR (600 MHz, D2O) δ 7.90 (d, J=8.4 Hz, 1H), 5.89-5.93 (m, 2H), 5.48 (dd, J=6.6, 3.0 Hz, 1H), 4.30-4.32 (m, 2H), 4.20-4.23 (m, 2H), 4.08-4.15 (m, 2H), 3.99 (d, J=10.8 Hz, 1H), 3.77 (t, J=9.6 Hz, 1H), 3.45 (d, J=13.2 Hz, 1H), 3.40 (t, J=9.6 Hz, 1H), 3.11 (t, J=12.6 Hz, 1H), 2.02 (s, 3H). 13C NMR (150 MHz, D2O) δ 174.94, 166.39, 151.96, 141.84, 102.79, 94.33, 88.82, 83.29 (J=9.0 Hz), 73.92, 71.82, 69.80, 69.28, 65.30, 53.64 (J=8.9 Hz), 40.70, 22.21. HRMS (ESI) m/z calcd for C17H28N4O16P2 (M+H)− 607.1054, found 607.1068.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography (EtOAc:MeOH:H2O=3:2:1, by volume)

Sources & evidence

ORD record
ord-429fd33577734af39f7d7bf9d28d1cb6
Source dataset
uspto-grants-2016_03
Patent number
US09290530B2

Reaction notes

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