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New Methods for the Synthesis of Novel Phenylpropanoid Glucose Esters
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Phenylpropanoid glycosides are naturally occurring compounds, most commonly appearing in fruits and vegetables that possess biological activities such as antiviral, antimicrobial, antioxidant, antifungal and many others. They are composed of a sugar that is linked (with a glycoside linkage) to a hydroxycinnamoyl residue and/or another group. These types of compounds have been used in Asian traditional medicine for many years but only recently they began to be studied and synthetized for further uses. The reason behind this is the low percentage of these esters in the natural sources and the relatively high complexity of the carbohydrate molecules.
In this project we aimed to develop and optimize protocols for the synthesis of phenylpropanoid esters of glucose and methylglucopyranose substituted with a cinnamic acid moiety. In order to achieve that three different esterification techniques were tested; the Steglich esterification, the Mitsunobu esterification and transesterification through enzymatic catalysis. The first two being well known and established procedures and the last being a “greener” alternative that has an enormous potential in carbohydrate synthesis.
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glucose phenylpropanoid esters esterification transesterification Mitsunobu Steglich