Browsing by Author "Mulani, Shaheen K."

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A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides
(2014-01-01)
Mulani, Shaheen K.
;
Guh, Jih-Hwa
;
Mong, Kwok-Kong Tony
;
應用化學系
;
Department of Applied Chemistry
A general strategy for the synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3 and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formyl morpholine modulated glycosylation methods for the construction of 1,2-trans beta- and alpha-glycosidic bonds. The reported strategy does not invoke the use of the participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. A preliminary study of the anti-proliferation properties of the PhG compounds 1-4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation.
A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides
(2014-01-01)
Mulani, Shaheen K.
;
Guh, Jih-Hwa
;
Mong, Kwok-Kong Tony
;
交大名義發表
;
National Chiao Tung University
A general strategy for the synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3 and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formyl morpholine modulated glycosylation methods for the construction of 1,2-trans beta- and alpha-glycosidic bonds. The reported strategy does not invoke the use of the participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. A preliminary study of the anti-proliferation properties of the PhG compounds 1-4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation.
General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses
(2015-11-20)
Mulani, Shaheen K.
;
Cheng, Kuang-Chun
;
Mong, Kwok-Kong T.
;
應用化學系
;
Department of Applied Chemistry
A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
Modulating glycosylation with exogenous nucleophiles: an overview
(2014)
Mulani, Shaheen K.
;
Hung, Wei-Cheng
;
Ingle, Arun B.
;
Shiau, Kai-Sheng
;
Mong, Kwok-Kong Tony
The major challenge in carbohydrate synthesis is stereochemical control of glycosidic bond formation. Different glycosylation methods have been developed that are based on the modulation effect of external nucleophiles. This review highlights the development, synthetic application, challenges and outlook of the modulated glycosylation methods.