This summer, James Greisler '10 (Galway, N.Y.) is researching the synthesis and medical application of carbohydrates under the guidance of Assistant Professor of Chemistry Professor Nicole Snyder. Greisler has been working on synthesizing different carbohydrate molecules that can later be used to develop new drugs, such as those used for cancer treatment. He is continuing to work on two carbohydrate projects that he began with Snyder last summer.
Carbohydrate molecules have special properties that make them useful for developing drugs. They are versatile, flexible, and soluble, and they interact uniquely with cell receptors. Greisler's first project involves developing a better method of synthesizing septanose carbohydrates, unusual molecules that have seven ringed sugars rather than the natural six. This extra member in the ring increases the molecule's flexibility, making it ideal for studying protein-carbohydrate interactions. The three current septanose synthesis methods all have critical disadvantages, including poor yields and high costs. To synthesize septanose molecules with a good yield and from low cost materials, Greisler has developed a new 6-step synthesis process.
In this synthesis process, he has found the most difficult part to be the bond migration, a step necessary to fuse the seven members of the ring together. Greisler has tried many different catalysts to generate the bond migration, but until recently, none of these catalysts produced the desired results. A few weeks ago, however, through the recommendation of a South African chemist, Greisler discovered a successful catalyst. Using this catalyst, he has obtained good results, and anticipates completing the septanose synthesis soon. The final products of the septanose synthesis will have a highly reactive alkene bond on which the functional groups used to make drugs can be added.
For Greisler's second project, he is working with researchers at the University of Southern Florida in an effort to develop improved anti-cancer drugs. Current anti-cancer drugs use porphyrins, molecules that absorb directed laser light and use it to kill tumor cells. Although porphyrin's ability to kill tumor cells is clearly advantageous, porphyins also destroy healthy body cells. However, attaching a carbohydrate to a porphyin molecule causes the porphyrin only to bind to the tumor cells, eliminating this undesired effect. Carbophyrins, or porphyrin molecules with attached carbohydrates, also increase a drug's solubility in the body.
Greisler's role in the production of carbophyrins is to create four types of the carbohydrates that will later be attached to porphyrins. Synthesizing these specific carbohydrates is quite difficult, for the process requires a great deal of purification and often yields by-products that are hard to separate from the carbohydrates. So far, Greisler has been able to create two, which Professor Snyder has taken with her to the University of Southern Florida. She is currently using the carbohydrates that Greisler synthesized as she learns how to attach them to porphyrins.
Greisler, a double major in Chemistry and Theater, says that he became interested in conducting research at Hamilton in order to help him decide whether or not to pursue a career path in research. While he thoroughly enjoys his chemistry research, he also has a passion for theater, and thus remains undecided about his future career plans. In addition to his involvement in several theater department productions, Greisler performs on the X-Viper Hour Radio Show and plays the trumpet in the Brass Ensemble.
-- by Stephanie Anglin '10
Carbohydrate molecules have special properties that make them useful for developing drugs. They are versatile, flexible, and soluble, and they interact uniquely with cell receptors. Greisler's first project involves developing a better method of synthesizing septanose carbohydrates, unusual molecules that have seven ringed sugars rather than the natural six. This extra member in the ring increases the molecule's flexibility, making it ideal for studying protein-carbohydrate interactions. The three current septanose synthesis methods all have critical disadvantages, including poor yields and high costs. To synthesize septanose molecules with a good yield and from low cost materials, Greisler has developed a new 6-step synthesis process.
In this synthesis process, he has found the most difficult part to be the bond migration, a step necessary to fuse the seven members of the ring together. Greisler has tried many different catalysts to generate the bond migration, but until recently, none of these catalysts produced the desired results. A few weeks ago, however, through the recommendation of a South African chemist, Greisler discovered a successful catalyst. Using this catalyst, he has obtained good results, and anticipates completing the septanose synthesis soon. The final products of the septanose synthesis will have a highly reactive alkene bond on which the functional groups used to make drugs can be added.
For Greisler's second project, he is working with researchers at the University of Southern Florida in an effort to develop improved anti-cancer drugs. Current anti-cancer drugs use porphyrins, molecules that absorb directed laser light and use it to kill tumor cells. Although porphyrin's ability to kill tumor cells is clearly advantageous, porphyins also destroy healthy body cells. However, attaching a carbohydrate to a porphyin molecule causes the porphyrin only to bind to the tumor cells, eliminating this undesired effect. Carbophyrins, or porphyrin molecules with attached carbohydrates, also increase a drug's solubility in the body.
Greisler's role in the production of carbophyrins is to create four types of the carbohydrates that will later be attached to porphyrins. Synthesizing these specific carbohydrates is quite difficult, for the process requires a great deal of purification and often yields by-products that are hard to separate from the carbohydrates. So far, Greisler has been able to create two, which Professor Snyder has taken with her to the University of Southern Florida. She is currently using the carbohydrates that Greisler synthesized as she learns how to attach them to porphyrins.
Greisler, a double major in Chemistry and Theater, says that he became interested in conducting research at Hamilton in order to help him decide whether or not to pursue a career path in research. While he thoroughly enjoys his chemistry research, he also has a passion for theater, and thus remains undecided about his future career plans. In addition to his involvement in several theater department productions, Greisler performs on the X-Viper Hour Radio Show and plays the trumpet in the Brass Ensemble.
-- by Stephanie Anglin '10
