Journal
CHEMISTRY & BIODIVERSITY
Volume 18, Issue 7, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbdv.202100135
Keywords
morphine; O ligands; hapten; protonation; NMR spectroscopy
Funding
- Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences
- Bolyai+New National Excellence Program [UNKP-20-5]
- Ministry for Innovation and Technology
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Morphine derivatives with C-3 phenolic hydroxy group can be used for synthesizing 3-O-functionalized molecules, which are suitable for immunization and immunoassays. Using ethyl bromo- and chloroacetate as O-alkylating agents allows the production of 3-O-carboxyalkyl derivatives with free carboxylic groups for further modification and conjugation.
The C-3 phenolic hydroxy group containing morphine derivatives (morphine, oxymorphone, naloxone, naltrexone) are excellent candidates for the synthesis of 3-O-functionalized molecules. Achieving free carboxylic group containing derivatives gives the opportunity for further modification and conjugation that could be used for immunization and immunoassays. For this purpose ethyl bromo- and chloroacetate can be used as O-alkylating agents. Hydrolyzing the products affords the appropriate free carboxylic group containing 3-O-carboxyalkyl derivatives. As these molecules contain an acidic and a basic functional group the protonation macro- and microconstants were determined too, using pH-potentiometry and NMR-pH titration, beside fully characterizing their structure using IR, CD, NMR and HR-MS measurements.
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