Textbook Question
Draw the structures of the following nucleotides.
(c) cyclic guanosine monophosphate (cGMP)
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Ch. 23 - Carbohydrates and Nucleic Acids
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 23, Problem 63a
Draw the structures of the following nucleotides.
(a) guanosine triphosphate (GTP)
Verified step by step guidance1
Understand the structure of guanosine triphosphate (GTP): GTP is a nucleotide composed of three main components: (1) a guanine base, (2) a ribose sugar, and (3) three phosphate groups attached in a triphosphate chain.
Start by drawing the guanine base: Guanine is a purine base with a fused double-ring structure containing nitrogen atoms. It has a keto group (=O) at position 6 and an amino group (-NH2) at position 2.
Attach the ribose sugar to the guanine base: Ribose is a five-carbon sugar. Connect the 1' carbon of the ribose to the N9 position of the guanine base via a β-glycosidic bond.
Add the triphosphate group: Attach the first phosphate group to the 5' carbon of the ribose sugar via a phosphoester bond. Then, link two additional phosphate groups to the first phosphate via phosphoanhydride bonds, forming the triphosphate chain.
Verify the structure: Ensure that all bonds are correctly drawn, the guanine base is properly connected to the ribose sugar, and the triphosphate chain is attached to the 5' carbon of the ribose. Confirm that the overall structure represents guanosine triphosphate (GTP).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleotide Structure
Nucleotides are the building blocks of nucleic acids, consisting of three main components: a nitrogenous base, a five-carbon sugar (ribose or deoxyribose), and one or more phosphate groups. In the case of guanosine triphosphate (GTP), the nitrogenous base is guanine, the sugar is ribose, and there are three phosphate groups attached to the sugar.
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Naming Nucleosides and Nucleotides Concept 2
Phosphate Groups
Phosphate groups are key components of nucleotides that play a crucial role in energy transfer and storage within cells. In GTP, the three phosphate groups are linked by high-energy bonds, and the hydrolysis of these bonds releases energy, which is utilized in various biochemical processes, including protein synthesis and signal transduction.
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Base Pairing and Function
The nitrogenous base in nucleotides, such as guanine in GTP, is essential for base pairing in nucleic acids. GTP not only serves as a building block for RNA but also functions as an energy source and a signaling molecule in cellular processes. Understanding the role of GTP in these contexts is vital for grasping its importance in biochemistry.
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Related Practice
Textbook Question
Some protecting groups can block two OH groups of a carbohydrate at the same time. One such group is shown here, protecting the 4-OH and 6-OH groups of β-d-glucose.
(a) What type of functional group is involved in this blocking group?
(b) What did glucose react with to form this protected compound?
(c) When this blocking group is added to glucose, a new chiral center is formed. Where is it? Draw the stereoisomer that has the other configuration at this chiral center. What is the relationship between these two stereoisomers of the protected compound?
(d) Which of the two stereoisomers in part (c) do you expect to be the major product? Why?
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Textbook Question
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the hydrolysate is found to be tagatose. The following information is known about tagatose:
(1) Molecular formula C6H12O6
(2) Undergoes mutarotation.
(3) Does not react with bromine water.
(4) Reduces Tollens reagent to give D-galactonic acid and D-talonic acid.
(5) Methylation of tagatose (using excess CH3I and Ag2O) followed by acidic hydrolysis gives 1,3,4,5-tetra-O-methyltagatose.
(a) Draw a Fischer projection structure for the open-chain form of tagatose.
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Textbook Question
Draw the structure of a four-residue segment of DNA with the following sequence. (3′end) G-T-A-C (5′ end)
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Textbook Question
An important protecting group developed specifically for polyhydroxy compounds like nucleosides is the tetraisopropyldisiloxanyl group, abbreviated TIPDS, that can protect two alcohol groups in a molecule.
(a) The TIPDS group is somewhat hindered around the Si atoms by the isopropyl groups. Which OH is more likely to react first with TIPDS chloride? Show the product with the TIPDS group on one oxygen.
(b) Once the TIPDS group is attached at the first oxygen, it reaches around to the next closest oxygen. Show the final product with two oxygens protected.
(c) The unprotected hydroxy group can now undergo reactions without affecting the protected oxygens. Show the product after the protected nucleoside from (b) is treated with tosyl chloride and pyridine, followed by NaBr, ending with deprotection with Bu4NF.
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Textbook Question
Draw the structures of the following nucleotides.
(b) deoxycytidine monophosphate (dCMP)
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