Carbamate → D-Glucosamine
Reaction equation
CS(C)=[O:3].[O:5]1[CH2:10][CH2:9][O:8]CC1.[N:11]1[CH:16]=CC=CC=1.[C:17](=[O:20])([O-:19])N.C(N([CH2:26][CH3:27])CC)C>>[OH:19][CH:17]1[O:20][C@H:27]([CH2:26][OH:3])[C@@H:9]([OH:8])[C@H:10]([OH:5])[C@H:16]1[NH2:11]Participants
Procedure
Dissolve chitosan oligosaccharides or glycol chitin in a suitable anhydrous organic solvent, such as dimethylsulfoxide (DMSO), dioxane, or pyridine, and adjust the pH to about 9.5-10 with triethylamine. Add the amount of the carbonyl-containing carbamate intermediate required to yield a specified degree of incorporation (0.05 to 1 group/glucosamine residue), and let react for about 12 to 18 hours at 40° C., protected from moisture. Add about 6-8 volumes of cold ethanol to the reaction and let stand at 4° C. for 24-48 hours to precipitate the polysaccharide-aromatic aldehyde conjugate. Redissolve the derivatized oligo- or polysaccharide in water, DMF, or DMSO, and re-precipitate again with 6-8 volumes of ethanol or other suitable solvent. Determine the efficacy of the coupling from the UV spectra. Dissolve the polysaccharide-aromatic aldehyde conjugate in water and lyophilize.
Sources & evidence
- ORD record
- ord-e8d52558562f4e97a4174c0668933119
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573245B1
Reaction notes
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