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A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. In the most common nucleotides the base is a derivative of purine or pyrimidine, and the sugar is pentose - deoxyribose or ribose.

Nucleotides are the structural units of RNA, DNA, and several cofactors - CoA, FAD, FMN, NAD, and NADP. In the cell they play important roles in energy production, metabolism, and signaling.

The structure elements of the most common nucleotides

Nomenclature[edit | edit source]

Nucleotide codes
Code Equivalence Complement
A A T or U
C C G
G G C
T or U T A
M A or C K
R A or G Y
W A or T W
S C or G S
Y C or T R
K G or T M
V A or C or G B
H A or C or T D
D A or G or T H
B C or G or T V
X or N A or C or G or T X

Nucleotide names are abbreviated into standard four-letter codes. The first letter is lower case and indicates whether the nucleotide in question is a ribonucleotide (r) or deoxyribonucleotide (d). The second letter indicates the nucleoside corresponding to the nucleobase:

G: Guanine
A: Adenine
T: Thymine
C: Cytosine
U: Uracil not usually present in DNA, but takes the place of Thymine in RNA

The third and fourth letters indicate the length of the attached phosphate chain (Mono-, Di-, Tri-) and the presence of a phosphate (P).

For example, deoxy-cytidine-triphosphate is abbreviated as dCTP.

Chemical structures[edit | edit source]

Nucleotides[edit | edit source]

Chemical structure of adenosine monophosphate
Adenosine monophosphate
AMP
Chemical structure of adenosine diphosphate
Adenosine diphosphate
ADP
Chemical structure of adenosine triphosphate
Adenosine triphosphate
ATP
Chemical structure of guanosine monophosphate
Guanosine monophosphate
GMP
Chemical structure of guanosine diphosphate
Guanosine diphosphate
GDP
Chemical structure of guanosine triphosphate
Guanosine triphosphate
GTP
Chemical structure of thymidine monophosphate
Thymidine monophosphate
TMP
Chemical structure of thymidine diphosphate
Thymidine diphosphate
TDP
Chemical structure of thymidine triphosphate
Thymidine triphosphate
TTP
Chemical structure of uridine monophosphate
Uridine monophosphate
UMP
Chemical structure of uridine diphosphate
Uridine diphosphate
UDP
Chemical structure of uridine triphosphate
Uridine triphosphate
UTP
Chemical structure of cytidine monophosphate
Cytidine monophosphate
CMP
Chemical structure of cytidine diphosphate
Cytidine diphosphate
CDP
Chemical structure of cytidine triphosphate
Cytidine triphosphate
CTP

Deoxynucleotides[edit | edit source]

Chemical structure of deoxyadenosine monophosphate
Deoxyadenosine monophosphate
dAMP
Chemical structure of deoxyadenosine diphosphate
Deoxyadenosine diphosphate
dADP
Chemical structure of deoxyadenosine triphosphate
Deoxyadenosine triphosphate
dATP
Chemical structure of deoxyguanosine monophosphate
Deoxyguanosine monophosphate
dGMP
Chemical structure of deoxyguanosine diphosphate
Deoxyguanosine diphosphate
dGDP
Chemical structure of deoxyguanosine triphosphate
Deoxyguanosine triphosphate
dGTP
Chemical structure of deoxythymidine monophosphate
Deoxythymidine monophosphate
dTMP
Chemical structure of deoxythymidine diphosphate
Deoxythymidine diphosphate
dTDP
Chemical structure of deoxythymidine triphosphate
Deoxythymidine triphosphate
dTTP
Chemical structure of deoxyuridine monophosphate
Deoxyuridine monophosphate
dUMP
Chemical structure of deoxyuridine diphosphate
Deoxyuridine diphosphate
dUDP
Chemical structure of deoxyuridine triphosphate
Deoxyuridine triphosphate
dUTP
Chemical structure of deoxycytidine monophosphate
Deoxycytidine monophosphate
dCMP
Chemical structure of deoxycytidine diphosphate
Deoxycytidine diphosphate
dCDP
Chemical structure of deoxycytidine triphosphate
Deoxycytidine triphosphate
dCTP

Synthesis[edit | edit source]

Natural[edit | edit source]

Purine ribonucleotides[edit | edit source]

The synthesis of IMP.
The color scheme is as follows: enzymes, coenzymes, substrate names, metal ions, inorganic molecules

The biosynthetic origins of purine ring atoms

By using a variety of isotopically labeled compounds it was demonstrated that N1 of purines arises from the amine group of Asp; C2 and C8 originate from formate; N3 and N9 are contributed by the amide group of Gln; C4, C5 and N7 are derived from Gly; and C6 comes from HCO3- (CO2).

The de novo synthesis of purine nucleotides by which these precursors are incorporated into the purine ring, proceeds by a 10 step pathway to the branch point intermediate IMP, the nucleotide of the base hypoxanthine. AMP and GMP are subsequently synthesized from this intermediate via separate, two step each, pathways. Thus purine moieties are initially formed as part of the ribonucleotides rather than as free bases. Six enzymes take part in IMP synthesis. Three of them are multifunctional - GART (reactions 2, 3, and 5), PAICS (reactions 6, and 7) and ATIC (reactions 9, and 10).

Reaction 1. The pathway starts with the formation of PRPP. PRPS1 is the enzyme that activates R5P, which is primarily formed by the pentose phosphate pathway, to PRPP by reacting it with ATP. The reaction is unusual in that a pyrophosphoryl group is directly transferred from ATP to C1 of R5P and that the product has the α configuration about C1. This reaction is also shared with the pathways for the synthesis of the pyrimidine nucleotides, Trp, and His. As a result of being on (a) such (a) major metabolic crossroad and the use of energy, this reaction is highly regulated.

Reaction 2. In the first reaction unique to purine nucleotide biosynthesis, PPAT catalyzes the displacement of PRPP's pyrophosphate group (PPi) by Gln's amide nitrogen. The reaction occurs with the inversion of configuration about ribose C1, thereby forming β-5-phosphorybosylamine (5-PRA) and establishsing the anomeric form of the future nucleotide. This reaction which is driven to completion by the subsequent hydrolysis of the released PPi, is the pathway's flux generating step and is therefore regulated too.

Reaction 3.

Pyrimidine ribonucleotides[edit | edit source]

The synthesis of UMP.
The color scheme is as follows: enzymes, coenzymes, substrate names, inorganic molecules

See also[edit | edit source]

External links[edit | edit source]

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