The differentiation between two identical chemical groups in the
Ca'a"bd
molecule in enzymic reactions is discussed first. It is then shown that squalene biosynthesized from two molecules of [1-D
2
]farnesyl pyrophosphate is asymmetrically labelled at one of its central methylene carbon atoms, one of the deuterium atoms at C-l of one of the two farnesyl residues having been replaced stereospecifically by H
B
of reduced nicotinamide adenine dinucleotide phosphate. The trideuterio succinic acid obtained by ozonolysis from such squalene is shown to be dextrorotatory and to have the
S
absolute configuration. The steric position of H
A
and of H
B
at position 4 of the dihydronicotinamide ring in NADH and NADPH, transferred from substrates to coenzyme by ‘A’- and ‘B’-specific dehydrogenases respectively, is deduced. This was achieved by making a correlation between the laevorotatory 2
R
-[2-D
1
]succinic acid (made chemically from enzymically generated 2
S
-3
R
-[3-D
1
]malic acid) and the [2-D
1
]succinic acids derived by chemical degradation from positions 3, 4, 5 and 6 of the dihydronicotinamide ring of ‘A’-deuterio and ‘B’-deuterio NADH. The absolute configuration of C-4 of the dihydronicotinamide ring in ‘A’-deuterio NADH is
R
and in the ‘B’-deuterio NADH it is
S
.