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

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Organic Chemistry Research

• Natural Product Synthesis
• Ripostatin Antibiotics
• Myxobacterium
• Handedness
• The Process
• The Big Picture

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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.

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Why Its 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 19812002.
• 61 of those can be traced to or were inspired by
  natural products J. Nat. Prod., 66, 1022
  (2003).

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Ripostatins Potential New Antibiotics
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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.

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Myxobacterium

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

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Organic Molecules are Handed

• They have a particular arrangement in
  3-dimensional space.
• The left and the right hand are not
  superimposable

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Example of Handedness with Molecules
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OUR GOAL

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

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The Process

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

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Sun, J. Zhu, C. Dai, Z. Yang, M. Pan, Y. Hu,
H.Journal of Organic Chemistry 2004, 69,
8500-8503.
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Our reaction
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• 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

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The Bottom Line Our Molecules 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!!)

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Big Picture
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Sources

• http//www.naturalingredient.org/naturalingredient
  s.htm
• http//pubs.acs.org/cen/coverstory/8141/8141pharma
  ceuticals.html
• http//encyclopedia.laborlawtalk.com/myxobacteria

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Acknowledments

• Howard Hughes Medical Institiute
• Kim Minor
• Haverford College
• Fran (not Blasé) Blase
• Doug, Aaron, and Hernan

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Clean Glassware
Dirty Glassware
Aaron and Doug