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Ladderane
Ladderane-2D.svg
IUPAC name
Properties
Molecular formula C2n+2H2n+6
Related compounds
Related compounds Cyclobutane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

A ladderane is an organic molecule containing two or more fused rings of cyclobutane. The name is a portmanteau because the serial cyclobutane rings look like a ladder and are singly bonded like alkanes. Ladderanes, like other cyclic rings, can be formed by the reduction of a carbon-carbon double bond into a single bond, concomitant with the creation of a new carbon-carbon bond to close the ring.[1][2]

The geometry of ladderanes is highly strained because ligands to the carbon atoms cannot extend to their ideal angles. However, examples of ladderanes have been found in living organisms.[1] An example is pentacycloanammoxic acid[3] which is composed of 5 fused cyclobutane units. It is found in bacteria performing the anammox process where it forms part of a tight and very dense membrane believed to protect the organism from toxic hydroxylamine and hydrazine involved in the production of nitrogen and water from nitrite ions and ammonia. [4]

Pentacycloanammoxic acid

References

  1. ^ a b Nouri, D H, Tantillo, D J (2006). "They Came from the Deep: Syntheses, Applications, and Biology of Ladderanes". Curr. Org. Chem. 10: 2055–2074. doi:10.2174/138527206778742678.  
  2. ^ Nouri, D H and Tantillo, D J. "Ladderane Formation Mechanisms: The Uphill Battle". 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006. pp. COMP 247.  
  3. ^ J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten (2002). "Linearly concatenated cyclobutane lipids form a dense bacterial membrane". Nature 419: 708–712. doi:10.1038/nature01128.  
  4. ^ Vincent Mascitti and E. J. Corey (2006). "Enantioselective Synthesis of Pentacycloanammoxic Acid". J. Am. Chem. Soc. 128 (10): 3118. doi:10.1021/ja058370g.  

See also

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