GUANYLIC ACID

Guanylic acid, also known as guanosine monophosphate (GMP), is a nucleotide composed of the nucleoside guanosine attached to a phosphate group. 
It is a key building block of RNA and plays an important role in cellular metabolism and signal transduction. 
Guanylic acid participates in many biochemical processes, including serving as a precursor for the synthesis of guanine nucleotides and involvement in energy transfer within the cell.

CAS Number: 5833-33-5
Synonyms
Guanosine monophosphate (GMP),Guanylate,5'-Guanidylic acid,5'-Guanosine monophosphate
Guanosine 5'-monophosphate,Guanosine 5′-phosphate,5'-Guanylic acid,5'-GMP

Introduction
Guanylic acid (GMP), also known as guanosine monophosphate, is a nucleotide comprising the nucleobase guanine, a ribose sugar, and one phosphate group. 
It is one of the four monomeric units that form RNA and participates in DNA synthesis after conversion to deoxy derivatives. 
GMP plays crucial roles in cellular energy transfer, enzyme regulation, and acts as a precursor for cyclic GMP, a vital second messenger. 
This article explores the intricate nature of GMP from molecular to applied science.

Chemical Structure and Properties
Molecular formula: C10H14N5O8P
Molecular weight: 363.2 g/mol
Structure: GMP consists of a guanine base linked to a ribose sugar at the 1’ carbon and a phosphate group attached at the 5’ carbon of the sugar.
Tautomerism: Guanine exists predominantly in the keto form under physiological conditions, enabling stable Watson-Crick base pairing.
Solubility: Highly soluble in water due to polar groups; insoluble in organic solvents.
pKa values: Phosphate group pKa ~1.0 and ~6.5 (diprotic acid character).
Stability: Sensitive to hydrolysis under extreme pH and temperature, but stable at physiological conditions.
Optical activity: Chiral ribose sugar confers optical activity.
Biosynthesis of Guanylic Acid
De Novo Synthesis Pathway
Starts from ribose-5-phosphate via phosphoribosyl pyrophosphate (PRPP).
Key enzymes: Amidophosphoribosyltransferase, IMP dehydrogenase, GMP synthetase.
Involves transformation of inosine monophosphate (IMP) to GMP by oxidation and amination.

Salvage Pathway
Guanine or guanosine recycled to GMP via hypoxanthine-guanine phosphoribosyltransferase (HGPRT).
Economical cellular mechanism conserving energy and nucleotides.

Regulation
Feedback inhibition by GMP on early enzymes regulates synthesis rate.
Interaction with ATP as an energy molecule balances purine nucleotide pools.

Guanylic Acid in Nucleic Acids
Incorporated into RNA during transcription by RNA polymerase.
GMP pairs with cytosine (C) via three hydrogen bonds, critical for RNA secondary structure.
GMP triphosphate (GTP) is the active substrate form in polymerization.
Deoxyguanylic acid (dGMP) is part of DNA, synthesized by ribonucleotide reductase.
Guanine nucleotides participate in RNA folding, splicing, and catalytic activities in ribozymes.

Enzymatic Functions Involving Guanylic Acid
GMP Kinase: Converts GMP to GDP in nucleotide metabolism.
Nucleotidases: Hydrolyze GMP to guanosine, regulating nucleotide pools.
Guanylate Cyclase: Converts GTP to cyclic GMP (cGMP), a key signaling molecule.
GTPases: Enzymes that hydrolyze GTP to GDP and GMP regulate cellular processes like signal transduction and protein synthesis.

Guanylic Acid in Signal Transduction
GMP derivatives like cGMP function as second messengers in pathways regulating vasodilation, phototransduction, and platelet aggregation.
cGMP activates protein kinase G (PKG), which phosphorylates target proteins affecting cell function.
GMP is involved indirectly in G-protein coupled receptor (GPCR) signaling through GTP-binding proteins.

Analytical Methods for Guanylic Acid
Chromatography
High-performance liquid chromatography (HPLC) with UV detection for quantification.
Ion-exchange chromatography for nucleotide separation.

Spectroscopy
UV-Vis absorbance at 254 nm due to guanine base.
Nuclear Magnetic Resonance (NMR) to elucidate structure and dynamics.

Mass Spectrometry
Electrospray ionization (ESI-MS) for molecular weight confirmation and metabolite identification.

Enzymatic Assays
Coupled enzyme assays measuring GMP kinase activity.

Industrial and Biotechnological Applications
Used as flavor enhancer in food industry (monosodium guanylate, MSG analog).
Substrate for enzymatic synthesis of cGMP analogs in pharmaceutical development.
Biotechnological production through microbial fermentation with genetically engineered strains.
Utilized in nucleic acid-based therapeutics and diagnostics.

Guanylic Acid Derivatives and Analogues
Cyclic GMP (cGMP): Secondary messenger in cellular signaling.
Monosodium guanylate (MSG): Food additive for umami taste.
Synthetic analogues for therapeutic targeting of guanine nucleotide binding proteins.

Pharmacological Importance
Modulators of GMP-related enzymes are studied for cardiovascular diseases, erectile dysfunction, and glaucoma.
GMP analogs as antiviral and anticancer agents.
Targeting GMP metabolism pathways offers routes for antimicrobial drug development.

Guanylic Acid in Research and Medicine
Molecular biology research extensively uses GMP and its derivatives.
Investigations into GMP binding proteins elucidate mechanisms of signal transduction.
GMP metabolism disorders linked to immunodeficiency and cancer.
Role in RNA therapeutics and mRNA vaccine technologies.

Future Perspectives
Enhanced understanding of GMP’s roles in non-coding RNA and epigenetics.
Development of GMP-based biosensors for clinical diagnostics.
Genetic engineering for optimized GMP biosynthesis in industrial strains.
Novel GMP analogs with improved pharmacokinetics and targeted actions.

Conclusion
Guanylic acid is a cornerstone molecule in biochemistry with wide-ranging roles from the structural foundation of nucleic acids to crucial regulatory functions in signal transduction and metabolism. 
Advances in analytical techniques, biotechnology, and medicinal chemistry continue to expand our understanding and utilization of GMP, underscoring its centrality in life sciences and applied technologies.

SAFETY INFORMATION ABOUT GUANYLIC ACID
  
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product