Ladderane

The ladderans form a special group of substances within the org. Compounds of the cycloalkanes , which consist of cyclobutane rings fused linearly to one another .

The way the individual cyclobutane rings are linked creates a ladder-like structure, so that the name of the ladderane is derived from the English word ladder for German 'ladder'.

Ladderane nomenclature

The fenestrans are distinguished from the ladderans , in which cyclobutane rings within the molecule are also angular, i.e. H. here at an angle of 90 °. Cyclically closed ladderanes lead to the so-called prismans , to which the Cuban is also counted.

In the nomenclature of ladderans, 1 is added to the number ( n ) of bonds between the common carbon atoms of the individual cyclobutane rings ("bridge bonds") and the name 'ladderan' is prefixed with the number, so that, for example, 4-ladderan is a ladderan referred to, which has three bridge bonds and correspondingly four cyclobutane rings.

Ladderan lipids

In nature, Ladderane v. a. in certain bacteria from the Planctomycetes group . These bacteria are species that are capable of the so-called anammox metabolic pathway, in which ammonium is oxidized to elemental nitrogen . This process takes place in special cellular compartments called anammoxosomes . The membranes of these anammoxosomes consist to a large extent (e.g. over 50% in Candidatus Brocadia anammoxidans) of membrane lipids , in which ladderans are contained as components. An example of such a ladderan-containing membrane lipid is pentacycloanammoxic acid, which contains a ladderan made up of five cyclobutane rings.

literature

Dustin Nouri, Dean Tantillo: They Came From the Deep: Syntheses, Applications, and Biology of Ladderanes. In: Current Organic Chemistry , 2006, 10, pp. 2055-2074, doi : 10.2174 / 138527206778742678 .
Henning Hopf : Step by Step — From Nonnatural to Biological Molecular Ladders. In: Angewandte Chemie International Edition , 2003, 42, pp. 2822-2825, doi : 10.1002 / anie.200301650 .

Individual evidence

↑ ^a ^b Henning Hopf, Joel F. Liebman, H. Mark Perks: Cubanes, fenestranes, ladderanes, prismanes, staffanes and other oligocyclobutanoids . In: PATAI's Chemistry of Functional Groups . 2009. doi : 10.1002 / 9780470682531.pat0337 .
↑ Laura A. van Niftrik, John A. Fuerst, Jaap S. Sinninghe Damsté, J. Gijs Kuenen, Mike SM Jetten, Marc Strous: The anammoxosome: an intracytoplasmic compartment in anammox bacteria . In: Microbiology Letters . 233, 2009, pp. 7-13. doi : 10.1016 / j.femsle.2004.01.044 .

[hopf-1] Henning Hopf, Joel F. Liebman, H. Mark Perks: Cubanes, fenestranes, ladderanes, prismanes, staffanes and other oligocyclobutanoids . In: PATAI's Chemistry of Functional Groups . 2009. doi : 10.1002 / 9780470682531.pat0337 .

[niftrik-2] Laura A. van Niftrik, John A. Fuerst, Jaap S. Sinninghe Damsté, J. Gijs Kuenen, Mike SM Jetten, Marc Strous: The anammoxosome: an intracytoplasmic compartment in anammox bacteria . In: Microbiology Letters . 233, 2009, pp. 7-13. doi : 10.1016 / j.femsle.2004.01.044 .