This research attempts to provide a possible explanation to the chemical origin of 2-deoxy-D-ribose via an aldol reaction of acetaldehyde and D-glyceraldehyde. The sugar mixture is trapped with N,N-diphenylhydrazine for ease of purification and characterisation. The reaction is promoted by amino acids, amino esters and amino nitriles consistently giving selectivities in favour of 2-deoxy-D-ribose. This is the first example of an amino nitrile-promoted reaction. The research is developed further by exploring the formation of 2-deoxy-D-ribose in a "protocell" environment - a primitive cell. Here we suggest that primitive cells may have been simple hydrogel systems. A discussion of the characterisation and catalytic ability of small peptide-based structures is included.