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Synthesis and Biophysical Studies on 35-Deoxy Amphotericin B Methyl Ester
- Source :
- Chemistry - A European Journal. 15:7117-7128
- Publication Year :
- 2009
- Publisher :
- Wiley, 2009.
-
Abstract
- The use of molecular editing in the elucidation of the mechanism of action of amphotericin B is presented. A modular strategy for the synthesis of amphotericin B and its designed analogues is developed, which relies on an efficient gram-scale synthesis of various subunits of amphotericin B. A novel method for the coupling of the mycosamine to the aglycone was identified. The implementation of the approach has enabled the preparation of 35-deoxy amphotericin B methyl ester. Investigation of the antifungal activity and efflux-inducing ability of this amphotericin B congener provided new clues to the role of the 35-hydroxy group and is consistent with the involvement of double barrel ion channels in causing electrolyte efflux.
- Subjects :
- Molecular Structure
Stereochemistry
Chemistry
Organic Chemistry
Total synthesis
Hexosamines
General Chemistry
Biophysical Phenomena
Catalysis
chemistry.chemical_compound
Aglycone
Mechanism of action
Amphotericin B methyl ester
Amphotericin B
medicine
Structure–activity relationship
Glycosides
Efflux
medicine.symptom
Ion channel
medicine.drug
Subjects
Details
- ISSN :
- 09476539
- Volume :
- 15
- Database :
- OpenAIRE
- Journal :
- Chemistry - A European Journal
- Accession number :
- edsair.doi.dedup.....5b2e59591ccbced3136d9160b1109abb
- Full Text :
- https://doi.org/10.1002/chem.200900231