Carbohydrate-porphyrin conjugates have recently gained attention for their ability to serve as sensitizers for photodynamic therapy and as water soluble catalysts.  However, the synthesis of these molecules remains a significant challenge.  While traditional methods for the preparation of functionalized porphyrins, including the Adler and Longo and Lindsay methods have been used to access carbohydrate-porphyrin conjugates with some success, the desired products are generally produced in low yield and, in cases where selectivity is an issue, with limited selectivity.  Substitution reactions using glycosyl bromides and porphyrin alcohols have also been employed for the synthesis of carbohydrate-porphyrin conjugates.  However, the slow reaction times and low yields reported for these reactions have limited their mainstream use.  Here we present studies on a process for the direct conjugation of carbohydrates using via 1,3-dipolar cycloaddition.  The conjugation of several sugars including glucose, galactose and lactose, as well applications for the corresponding conjugates will be discussed.

Studies on the synthesis of carbohydrate-porphyrin conjugates via 1,3-dipolar cycloaddition

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.