Molecular biology 1 - nucleosides and nucleotides Flashcards
Role of nucleotides
- energy currency
- chemical links (second messengers) in cellular response to external stimuli (e.g. hormones)
- Form structure of enzyme cofactors (e.g. NAD) and metabolic intermediates
- form nucleic acids
2 types of nucleic acids
deoxyribonucleic acid (DNA), ribonucleic acid (RNA)
Functions of nucleic acids
transmit genetic information, protein synthesis
What are the monomers of nucleic acids (DNA and RNA)
(ribo/deoxyribo) nucleotides
What components make up a nucleotide?
pentose sugar, phosphate(s), nitrogenous base (nitrogenous, aromatic, heterocyclic ring) - phosphorylated nucleosides
pentose sugar in DNA
deoxyribose
pentose sugar in RNA
ribose
2 types of nitrogenous base
- pyrimidine - monocyclic
- purine (dicyclic ring - pyrimidine ring fused to imidazole ring)
What feature makes each nitrogenous base unique?
The attachment of NH2, CH3, and C=O groups
What are the purine bases?
adenine and guanine
What are the pyrimidine bases?
cytosine, thymine, uracil
Which group is found in adenine?
-NH2
Which group is found in guanine?
-C=O and -NH2
Which group is found in cytosine?
-NH2 (as well as C=O)
Which group is found in uracil?
C=O (2)
Which group is found in thymine?
C=O (2) and -CH3
How are the carbon atoms in the pentose sugar of the nucleotide numbered?
1’ to 5’ clockwise from O atom (prime ‘ indicates that the C atoms are of the sugar not the nitrogenous base)
Difference between ribose and deoxyribose
Attached to C2, ribose has an OH group whereas deoxyribose has a H group.
What components make up a nucleoside (e.g. adenosine)?
nitrogenous base and pentose sugar (linked by N-glycosidic bond)
What bond links the pentose sugar and nitrogenous base in nucleosides/nucleotides?
N-glycosidic bond (beta)
How does the N-glycosidic bond between the nitrogenous base and pentose sugar form?
Between 1’C of pentose sugar and N9 of purine or N1 of pyrimidine ring via a hydrolysis reaction.
Which OH group on the sugar is usually esterified by the addition of a phosphate to form a nucleotide (phosphate ester of nucleoside)?
OH group on 5’C (forms a nucleoside 5’-phosphate)
How are nucleosides named?
nucleoside + 5’ (usually 5’C) + (mono/di/tri) phosphate
Is AMP a ribonucleotide or deoxyribonucleotide?
Ribonucleotide (has OH group on 2’C)
How are the phosphates in a nucleotide named?
first / mono phosphate is alpha, second / di is beta, third / tri is gamma
unabbreviated name of AMP
adenosine 5’-monophosphate (deoxyadenylate)(ribonucleotide)
Unabbreviated name of dAMP
deoxyadenosine 5’-monophosphate (deoxyadenylate) (deoxyribonucleotide)
Which base cannot form a deoxyribonucleoside/deoxyribonucleotide?
Uracil
Which base cannot form a ribonucleoside/ribonucleotide?
Thymine
Name of deoxyribonucleoside formed with deoxyribose and adenine
deoxyadenosine
Name of ribonucleoside formed with ribose and adenine
adenosine
Which is the main NTP (nucleoside triphosphate) hydrolysed to provide chemical energy for cellular reactions?
ATP (adenosine 5’-triphosphate - a ribonucleotide)
Where is ATP produced?
in the mitochondrion
What is the bond that joins a ribose and alpha phosphate?
ester linkage
What is the bond that joins alpha-beta and beta-gamma phosphates?
phosphoanhydrides
Do ester bond or phosphoanhydride bond hydrolysis yield more energy?
Hydrolysis of each anhydride bond (30 kJ/mol) yields more energy than the ester bond (14 kJ/mol)
Which ribonucleoside forms part of the structure of many enzyme cofactors?
Adenosine (adenine+ribose)
Examples of enzyme cofactors which adenosine is a part of
NADP (nicotinamide adenine dinucleotide phosphate), NAD, FAD (flavin adenine dinucleotide), coenzyme A
Example of nucleotide that is a common second messenger
cAMP
Unabbreviated name of cAMP
adenosine 3’, 5’-cyclic monophosphate
How is cAMP synthesised?
From ATP in a reaction catalysed by adenyl cyclase
How is cAMP broken down?
cAMP is broken down into 5’ AMP by phosphodiesterase enzyme.
How does cAMP act as a second messenger?
- Hormone binds to receptors on plasma membrane
- stimulates adenyl cyclase
- increased cAMP produced
- cAMP acts inside cell to alter rate of processes
Example of cAMP action
cAMP binds to regulatory subunits of protein kinase A causing them to detach from the catalytic subunits. Protein kinase A is now activated
Examples of nucleotides as regulatory molecules
cAMP (adenosine 3’, 5’-cyclic monophosphate), cGMP, ppGpp (guanosine 5’-diphosphate 3’-diphosphate)
Function of cGMP
Regulatory functions in many cells (like cAMP)
Function of ppGpp
serve as starvation signals in bacteria causing large changes in metabolism by increasing or decreasing transcription of hundreds of genes
What is a gene?
A segment of DNA containing the information required for the synthesis of a functional biological product (RNA or protein).
How are successive nucleotides linked in nucleic acids?
phosphodiester bonds
Description of 3’ to 5’ phosphodiester bond
the 3’C of the sugar in a nucleotide is bonded to a phosphate group which is attached to the 5’C of the sugar in the adjacent nucleotide
What makes up the backbone of DNA?
Deoxyribose and phosphate linked by phosphodiester bridges
Structure of DNA double helix
2 antiparallel chains wound around each other in a right-handed double-helical arrangement
How is the DNA double helix held together?
Complementary base pairing ( 2 H bonds between A and T, 3 H bonds between C and G)
How far apart are the base pairs stacked?
3.4 A (10.5 base pairs per turn therefore each turn is about 34A long)
What grooves does the offset pairing of the 2 strands create in DNA?
Major and minor groove
Which bases are equivalent in number in the DNA molecule?
A=T, C=G (due to complementary strands)
Chargaff’s rule (4)
- base composition of DNA varies between species
- DNA specimens from the same species have the same base composition
- base composition of DNA doesn’t change with an organism’s age, nutrition or environment
- A=T and C=G therefore the number of purines=pyrimidines (A+G=C+T)
Where is RNA mainly found?
in the cytoplasm
What direction is the backbone of DNA?
5’ - 3’ backbone
How is RNA different to DNA?
- Uracil replaces thymine
- ribose replaces deoxyribose
- single-stranded
- more than one form of RNA (m/t/rRNA)
What are the only exceptions to RNA being single stranded?
Hairpin
How does a hairpin loop form in tRNA?
Close-proximity self-complementarity within each strand
Structure that can form when there is an inverted repeat sequence in DNA
Cruciform (4 way junction of 2 hairpin structures)
Order of RNA types abundance in cells
80% rRNA, 15% tRNA, 5% mRNA
What is the s unit used to measure a molecule’s size?
sedimentation coefficient (s)