TY - JOUR
T1 - Total synthesis and biological evaluation of transvalencin Z
AU - Nelson, Kathryn M.
AU - Salomon, Christine E.
AU - Aldrich, Courtney C.
PY - 2012/6/22
Y1 - 2012/6/22
N2 - The emerging global epidemic of drug-resistant tuberculosis has created an urgent need to identify novel therapeutic approaches for disease treatment. Transvalencin Z (1) is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure-activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a-d), and the absolute configurations were defined using chemical synthesis, HPLC retention times, and optical rotation measurements. Surprisingly, none of the transvalencin Z diastereomers exhibited any inhibitory activity against a panel of microbial pathogens, including several species of mycobacteria.
AB - The emerging global epidemic of drug-resistant tuberculosis has created an urgent need to identify novel therapeutic approaches for disease treatment. Transvalencin Z (1) is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure-activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a-d), and the absolute configurations were defined using chemical synthesis, HPLC retention times, and optical rotation measurements. Surprisingly, none of the transvalencin Z diastereomers exhibited any inhibitory activity against a panel of microbial pathogens, including several species of mycobacteria.
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U2 - 10.1021/np200972s
DO - 10.1021/np200972s
M3 - Article
C2 - 22616579
AN - SCOPUS:84866464360
SN - 0163-3864
VL - 75
SP - 1037
EP - 1043
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 6
ER -