Reckoning

Reckoning / Code of life / Bases and pairing

Code of life · the letters

Bases and pairing

Each letter of DNA is a base, a flat ring of carbon and nitrogen. Two are double rings, the purines adenine and guanine; two are single rings, the pyrimidines cytosine and thymine. RNA uses uracil in place of thymine. The edges of the bases carry hydrogen atoms and lone pairs placed so that A fits only T and G fits only C.

NH₂N12N3456N78Nto sugar (C1′)9
Adenine · purine
ONH₂NH12N3456N78Nto sugar (C1′)9
Guanine · purine
H₂NONto sugar (C1′)12N3456
Cytosine · pyrimidine
OOCH₃Nto sugar (C1′)12NH3456
Thymine · pyrimidine
OONto sugar (C1′)12NH3456
Uracil · pyrimidine

Skeletal formulas: each corner without a letter is a carbon atom, and hydrogens on carbon are not drawn. Small numbers are the standard ring numbering. Blue: nitrogen; red: oxygen. Checked when the site is built: counting the drawn atoms and filling each one’s valence with hydrogen gives the molecular formula in the table.

BaseRingFormulaGroupsIn
AAdeninepurineC₅H₅N₅amino group on C6DNA and RNA
GGuaninepurineC₅H₅N₅OC6=O (keto), amino group on C2DNA and RNA
CCytosinepyrimidineC₄H₅N₃Oamino group on C4, C2=ODNA and RNA
TThyminepyrimidineC₅H₆N₂O₂C2=O, C4=O, methyl group on C5DNA
UUracilpyrimidineC₄H₄N₂O₂C2=O, C4=ORNA

The pairs

NH₂NNNNto sugar (C1′)OOCH₃Nto sugar (C1′)NH
adenine · thymine: two hydrogen bonds
ONH₂NHNNNto sugar (C1′)H₂NONto sugar (C1′)N
guanine · cytosine: three hydrogen bonds

Red dashes are hydrogen bonds: a hydrogen on one base held by a nitrogen or oxygen on the other. A·T makes two, G·C makes three, so DNA rich in G and C holds its strands together more firmly and needs more heat to separate. The bonds to the sugars (bottom left and bottom right) lie the same distance apart in both pairs. Because of this, either pair fits the same helix, and the sequence can be anything at all. This was the key observation of Watson & Crick 1953.

The nucleotide

O1′2′3′4′5′PphosphateOH3′ end: the next phosphate joins here2′: H in DNA, OH in RNAbaseA, G, C, T (or U)

A nucleotide is a base on a sugar (deoxyribose in DNA, ribose in RNA) with a phosphate. The sugar’s carbons are numbered with primes: the phosphate hangs on 5′ and links to the 3′ carbon of the next sugar, so every strand has a direction, written 5′ → 3′. The two strands of a double helix run in opposite directions, which is why the partner of a sequence is read backwards: its reverse complement.

Then and now

Chargaff found in 1950 that DNA contains as much A as T and as much G as C, without knowing why. The answer was the pairing above (1953). The bases were drawn for years in other tautomeric forms, with hydrogens in different places; Watson and Crick’s model worked only once the keto and amino forms shown here were used.