beta-Maltose → alpha-Maltotriose

HRID 2400227Notes

Reaction equation

HRID 2400227 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:13]([OH:35])[C@H:14]1[O:19][C@H:18]([O:20][C@H:21]2[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@H:24]([OH:29])[O:23][C@@H:22]2[CH2:30][OH:31])[C@H:17]([OH:32])[C@@H:16]([OH:33])[C@@H:15]1O.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N.C(N[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O)(=O)C>>[CH2:11]([OH:12])[C@H:9]1[O:10][C@H:2]([O:1][C@H:15]2[C@H:16]([OH:33])[C@@H:17]([OH:32])[C@@H:18]([O:20][C@H:21]3[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@@H:24]([OH:29])[O:23][C@@H:22]3[CH2:30][OH:31])[O:19][C@@H:14]2[CH2:13][OH:35])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8]

Participants

5

Reactant 4

HCID 6255beta-MaltoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 439213D-GlucosamineHCID 439281N-Acetyl-D-Mannosamine

Product 1

HCID 192826alpha-Maltotriose

Procedure

D-Glucose (10 mg), D-maltose (10 mg) maltotriose (25 mg), D-glucosamine (10 mg) or N-acetyl-D-mannosamine (10 mg) were reacted with O-(3-thiolpropyl)hydroxylamine (6 mg) in 1 ml D2O adjusted to pH 5.5 with 30% solution of NaOD at 37° C. for 15 hours. Progress of reaction was monitored by 1H NMR. Maltotriose-SH (30 mg) was separated from linker by passing through BioBel P-2 column in 0.05 M pyridine acetate buffer as above and freeze-dried. Next 30 mg of maltotriose-SH was reacted with bromoacetamido-derivatized BSA (15 mg), prepared as above to form maltotriose-BSA conjugate by thioether linkages. Reaction was done in buffer A, pH 7.4, 3 hours and solution was purified on Sephadex G-100 column as above. Extent of conjugation was evaluated by MALDI-TOF. Molecular mass of bromoacetamido-BSA was 73545 Da, while maltotriose-BSA conjugate was 81673 Da, indicated incorporation of 16 maltotriose molecules per BSA.

Workup

  1. customProgress of reaction
  2. customMaltotriose-SH (30 mg) was separated from linker
  3. customfreeze-dried
  4. customNext 30 mg of maltotriose-SH was reacted with bromoacetamido-derivatized BSA (15 mg)
  5. customprepared as above

Sources & evidence

ORD record
ord-cace795e082b4b5dbc52f297c512b377
Source dataset
uspto-grants-2014_08
Patent number
US08795680B2

Reaction notes

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