A comment should be made to contrast aromatic with aliphatic organic compounds. Aliphatic hydrocarbons (also called paraffins) are straight-chain alkanes (i.e., compounds having the general formula CnH2n+2, where n is an integer greater than one) starting with methane (CH4) and increasing by –CH2– units as a homologous series to high molecular weights. They can form abiotically (CH4 to typically decane, under hydrous conditions even to > C35)2 and biotically by direct synthesis or by geological degradation of lipid and cell membrane detritus.3 Lipids are aliphatic homologous compounds (e.g., fatty acids, fatty alcohols, etc.) important as membrane components and for energy storage. They are currently biologically synthesized but can also form abiotically in aqueous media at elevated temperatures and pressures.4-6 Biomarkers are organic compounds with specific structures (e.g., cholestane) that can be related back to their natural product precursors. The natural products (e.g., cholesterol) are biosynthesized from lipid precursors.7 Homologous aliphatic organic compounds and biomarkers can be distinguished by organic geochemists as being derived from abiotic or biotic sources.8 The homologous compounds with the biomarkers should be considered as the intermediary organics between the CH4 chemistry on planetary bodies and the formation of aromatics in the solar and interstellar medium as additional suitable tracers for evidence of life.
Molecules are three-dimensional. A carbon atom with four single bonds lies at the center of a tetrahedron. The atoms to which the carbon is bonded are at the vertices of the tetrahedron. Those atoms are in turn likely to be bonded to other atoms. If the chemical structures at the four corners all differ, however slightly, the mirror images of the tetrahedron will not be superimposable (Figure 1.3).
Mirror-image stereoisomers that are not superimposable are called enantiomers; stereoisomers that are not enantiomers are called diastereomers. Enantiomers possess chirality, or handedness, and when dissolved rotate the plane of polarized light when it is passed through the solution.
Life on Earth makes use of only a limited number of diastereomers of all those that are possible.9 Moreover, biotic processes display an enantiomeric excess; e.g., left-handed amino acids and right-handed sugars almost exclusively predominate in living systems.
Carbon atoms bearing four different substituents are said to be chiral centers. If a molecule has n chiral centers it will, in most cases, have 2n stereoisomers. There will, for example, be 256 stereoisomers of a compound with eight chiral centers. Each will have exactly the same chemical formula and pattern of connectivity among its atoms (A is connected to B is connected to C and D, and so on). Only the arrangements of those atoms in space will differ, and there will be 256 variations. Life functions by using only a small subset of all possible stereoisomers.