Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbamate | HCID 276 | — |
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Product | D-Glucosamine | HCID 439213 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06573245B1 |
|---|
| Source dataset | uspto-grants-2003_06 |
|---|
| ORD ID | ord-e8d52558562f4e97a4174c0668933119 |
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| Source note | uspto-grants-2003_06 |
|---|
