Nucleic Acids in Chemistry and Biology

Introduction and Overview 5

N

N

N

N NH 2

O

HO

P O

OH

HO

O

N

N

N

N OH

O

HO

P O

OH

HO

O

NH 2

deoxyadenylic acid

[dAMP]

deoxycytidylic acid

[dCMP]

O

HO

P O

OH

HO

O

O

HO

P O

OH

HO

N O

N

NH 2

O

N

N

OH

O

H 3 C

deoxyguanylic acid

[dGMP]

(as enolic tautomer)

deoxythymidylic acid

[dTMP]

(as enolic tautomer)

Figure 1.3 Structures of 5
-deoxyribonucleotides (original tautomers for dGMP and dTMP)

N

N

N

N NH 2

O

HO

AcO

N

N

N

N NH 2

O

AcO

N HO

N

N

N NH 2

O

AcO

AcO

N

N

N

N NH 2

O

O

HO

OOHP

OH

N

N

N

N NH 2

O

HO

P O

O

HO

OH

i +

ii,iii

i, iv

ii,iii

i, iv

3'-dAMP 5'-dAMP

Figure 1.4 Todd’s synthesis of deoxyadenosine 3
- and 5
-phosphates Reagents: (i) MeOH, NH 3 (ii) (PhO) 2 P(O)
OP(H)(O)OCH 2 Ph (iii) N-chlorosuccinimide (iv) H 2 /PdC
(D.H. Hayes, A.M. Michelson and A.R. Todd, J. Chem. Soc., 1955, 808–815)