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Synthesizing a Key Piece for an Antibiotic Molecule Brought to you by : Latasha Anderson and Jacqueline Petroski Organic Chemistry Research Natural Product Synthesis Ripostatin Antibiotics Myxobacterium Handedness The Process The Big Picture Natural Product Synthesis

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Synthesizing a Key Piece for an Antibiotic Molecule

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Synthesizing a Key Piece for an Antibiotic Molecule

Brought to you by :

Latasha Anderson and Jacqueline Petroski


Organic Chemistry Research

  • Natural Product Synthesis

  • Ripostatin Antibiotics

  • Myxobacterium

  • Handedness

  • The Process

  • The Big Picture


Natural Product Synthesis

-A natural product is a “product (molecule) that is derived from plants, animals or microbial sources.

-They can have medicinal value.

-Synthesis means doing chemical reactions on a small molecule to add on or build up to bigger molecules.


Why It’s Important

  • For decades, natural products have been a wellspring of drugs and drug leads.

  • Penicillin (a miracle drug) was discovered around WWII . It came from a mold!

  • There were 877 new chemical molecules introduced as drugs worldwide during 1981–2002.

  • 61% of those can be traced to or were inspired by natural products [J. Nat. Prod., 66, 1022 (2003)].


Ripostatins: Potential New Antibiotics


Myxobacterium

  • Any of numerous gram-negative, rod-shaped saprophytic bacteria of the phylum Myxobacteria, typically found embedded in slime in which they form complex colonies and noted for their ability to move by gliding along surfaces without any known organ of locomotion.


Myxobacterium

-Bacteria that predominantly live in the soil and other places……..


Organic Molecules are Handed

  • They have a particular arrangement in 3-dimensional space.

  • The left and the right hand are not superimposable


Example of Handedness with Molecules


OUR GOAL

  • Our goal was to make a molecule called a sulfoxide and get as much purity in the handedness as possible.


We made a ligand that blocked one face of the molecule so that the reaction had to occur from the other face.

The Process


Sun, J.; Zhu, C.; Dai, Z.;Yang, M.; Pan, Y.; Hu, H.Journal of Organic Chemistry2004, 69, 8500-8503.


Our reaction


  • We left it in the freezer overnight.

  • Since there were some impurites in our reaction we went through three different steps for purification.

    ~Seperatory Funnel

    ~Flash Column Chromotagraphy/’Columning”

    ~Distilation


The Bottom Line: Our Molecule’s Handedness

  • We made a significant amount of sulfoxide (at least 12g(!) purified)

  • To check our molecules handedness we took an optical rotation and found that out of 100 molecules, 85 were ‘right’ handed and 15 were ‘left’ handed. (Not too shabby!!)


Big Picture


Sources

  • http://www.naturalingredient.org/naturalingredients.htm

  • http://pubs.acs.org/cen/coverstory/8141/8141pharmaceuticals.html

  • http://encyclopedia.laborlawtalk.com/myxobacteria


Acknowledments

  • Howard Hughes Medical Institiute

  • Kim Minor

  • Haverford College

  • Fran (not Blasé) Blase

  • Doug, Aaron, and Hernan


Clean Glassware

Dirty Glassware

Aaron and Doug


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