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Volumn 15, Issue 29, 2009, Pages 7117-7128

Synthesis and biophysical studies on 35-Deoxy amphotericin b methyl ester

Author keywords

Amphotericin b; Antifungal agents; Natural products; Structure activity relationship; Total synthesis

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENTS; NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIP; TOTAL SYNTHESIS;

EID: 67650665790     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900231     Document Type: Article
Times cited : (39)

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    • Treating 53 with LiOH led to formation of a complex mixture of products. A complex mixture of byproducts is also formed during azide reduction with basic triethylamine and 1,3-propanedithiol, The base sensitivity of amphotericin B derivatives is highly dependant on structure. Chemical evidence in support of this supposition is the fact that while saponification of amphotericin B methyl, ester (AME) with LiOH proceeds cleanly, hydrolysis of the acetonide protected amphotericin B methyl ester leads to epimerization, presumably at C34.
    • Treating 53 with LiOH led to formation of a complex mixture of products. A complex mixture of byproducts is also formed during azide reduction with basic triethylamine and 1,3-propanedithiol, The base sensitivity of amphotericin B derivatives is highly dependant on structure. Chemical evidence in support of this supposition is the fact that while saponification of amphotericin B methyl, ester (AME) with LiOH proceeds cleanly, hydrolysis of the acetonide protected amphotericin B methyl ester leads to epimerization, presumably at C34.
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    • The width of the phospholipid bilayer of these LUVs is 37 Â and thus any formation of single barrel ion channels should be precluded. See supporting information for additional measurements.
    • The width of the phospholipid bilayer of these LUVs is 37 Â and thus any formation of single barrel ion channels should be precluded. See supporting information for additional measurements.


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