Facilitated Attachment of the N-(3-HydroxypropyI) Urea Unit to a Solid Phase Resin Using 9- Fluorenylmethoxycarbonyl (FMOC) as a Protecting and Quantifying Group
Location
CSU Ballroom
Start Date
28-4-2009 10:00 AM
End Date
28-4-2009 12:00 PM
Student's Major
Chemistry and Geology
Student's College
Science, Engineering and Technology
Mentor's Name
Michael J. Lusch
Mentor's Department
Chemistry and Geology
Mentor's College
Science, Engineering and Technology
Description
In the search for new drug compounds, the current focus has been shifted to a class of compounds called peptidomimetics, which contain urea as possible drug candidates. Peptidominetics are compounds that mimics the biological activity of peptides but possess superior pharmacokinetic properties such as absorption, metabolic stability and a lower toxicity. Previous studies involving the synthesis of urea compounds have been done using solid phase synthesis and the toxic compound phosgene or one of its derivatives. Using a method similar to those used by Kearney, et al., the goal of my research is to see if I can synthesize 9-fluorenylmethoxycarbonyl isocyanate by the reaction of commercially available 9- fluorenylmethyl chloroformate with potassium cyanate. By using potassium cyanate instead of phosgene, the experiment becomes safer and reduces the number of steps needed to produce the isocyanate intermediate. Reaction of the FMOC isocyanate with an 0-protected 3-hydroxypropyl amine and removal of the O protecting group would then give an FMOC-protected N-(3-hydroxypropyl)urea which could be attached to a solid phase resin through its hydoxyl functional group. Removal of the FMOC group under standard conditions would then release the free resin-bound propylurea and would also allow the measurement of the amount of urea attached to the resin. Results from the research could lead to the creation of a library of compounds containing urea for further studies in the areas of chemical genetics and combinatorial chemistry. Future studies involving the collection of urea compounds could yield biologically active properties and new possible drug candidates.
Facilitated Attachment of the N-(3-HydroxypropyI) Urea Unit to a Solid Phase Resin Using 9- Fluorenylmethoxycarbonyl (FMOC) as a Protecting and Quantifying Group
CSU Ballroom
In the search for new drug compounds, the current focus has been shifted to a class of compounds called peptidomimetics, which contain urea as possible drug candidates. Peptidominetics are compounds that mimics the biological activity of peptides but possess superior pharmacokinetic properties such as absorption, metabolic stability and a lower toxicity. Previous studies involving the synthesis of urea compounds have been done using solid phase synthesis and the toxic compound phosgene or one of its derivatives. Using a method similar to those used by Kearney, et al., the goal of my research is to see if I can synthesize 9-fluorenylmethoxycarbonyl isocyanate by the reaction of commercially available 9- fluorenylmethyl chloroformate with potassium cyanate. By using potassium cyanate instead of phosgene, the experiment becomes safer and reduces the number of steps needed to produce the isocyanate intermediate. Reaction of the FMOC isocyanate with an 0-protected 3-hydroxypropyl amine and removal of the O protecting group would then give an FMOC-protected N-(3-hydroxypropyl)urea which could be attached to a solid phase resin through its hydoxyl functional group. Removal of the FMOC group under standard conditions would then release the free resin-bound propylurea and would also allow the measurement of the amount of urea attached to the resin. Results from the research could lead to the creation of a library of compounds containing urea for further studies in the areas of chemical genetics and combinatorial chemistry. Future studies involving the collection of urea compounds could yield biologically active properties and new possible drug candidates.
Recommended Citation
Phaengkhouane, Souksavanh. "Facilitated Attachment of the N-(3-HydroxypropyI) Urea Unit to a Solid Phase Resin Using 9- Fluorenylmethoxycarbonyl (FMOC) as a Protecting and Quantifying Group." Undergraduate Research Symposium, Mankato, MN, April 28, 2009.
https://cornerstone.lib.mnsu.edu/urs/2009/poster-session-C/25
