Acetaldehyde → (s,z)-2-(3-((1,3-Dihydroxy-2-(hydroxymethyl)propan-2-yl)(3-hydroxy-4,4-dimethoxybut-1-enyl)amino)propylamino)-2-(hydroxymethyl)propane-1,3-diol
Reaction equation
[Si](O[C@@H]1C[C@@H](CO)OC(=O)C1)([C:4](C)(C)[CH3:5])(C)C.[Na+].[Cl-].[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH:23]=[O:24].C(=O)C.[OH-].[Na+].[CH2:32]([CH2:42][NH:43][C:44]([CH2:49][OH:50])([CH2:47][OH:48])[CH2:45][OH:46])[CH2:33][NH:34][C:35]([CH2:40][OH:41])([CH2:38][OH:39])[CH2:36][OH:37]>>[OH:46][CH2:45][C:44]([N:43](/[CH:4]=[CH:5]\[C@H:23]([OH:24])[CH:22]([O:25][CH3:26])[O:21][CH3:20])[CH2:42][CH2:32][CH2:33][NH:34][C:35]([CH2:36][OH:37])([CH2:38][OH:39])[CH2:40][OH:41])([CH2:47][OH:48])[CH2:49][OH:50]Participants
7
Reactant 6
Product 1
Conditions
- Temperature
- 37 °C
Procedure
To a solution of bis-tris propane [2] buffer (70 mL, 50 mM bis-tris propane, pH 8.0, 300 mM NaCl) and a solution of 2,2-dimethoxyethanal X′ (10 mL, 0.5 M in bis-tris propane buffer as described above), an aqueous solution of DERA 02 (10 mL, prepared with analogue method to one described in Example 1) and a solution of acetaldehyde (10 mL, 1.0 M in bis-tris propane buffer as described above) was added. The mixture was stirred for 3 h at 37° C. and pH was regulated at 8.0 with NaOH. After 3 h the proteins in the sample (1 mL) from the reaction mixture (100 mL) were precipitated with acetonitrile (9 mL) and the solution was centrifuged. A sample from the supernatant was collected and analyzed directly by HPLC-MS/MS instrument:
Workup
- customAfter 3 h the proteins in the sample (1 mL) from the reaction mixture (100 mL) were precipitated with acetonitrile (9 mL)
- customA sample from the supernatant was collected
Sources & evidence
- ORD record
- ord-e2df4a0c2daa4f4b8b27b8e94b210495
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183397B2
Reaction notes
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