Textbook Question
Draw the structures of the following nucleotides.
(a) guanosine triphosphate (GTP)
885
views
Ch. 23 - Carbohydrates and Nucleic Acids
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 63c
Draw the structures of the following nucleotides.
(c) cyclic guanosine monophosphate (cGMP)
Verified step by step guidance1
Understand the structure of guanosine: Guanosine is a nucleoside composed of the nitrogenous base guanine attached to a ribose sugar via a β-N-glycosidic bond. Familiarize yourself with the structure of guanine and ribose to begin constructing the molecule.
Add the phosphate group: In cyclic guanosine monophosphate (cGMP), a phosphate group is attached to the ribose sugar. Specifically, the phosphate forms a cyclic bond by connecting the 3'-hydroxyl group and the 5'-hydroxyl group of the ribose sugar.
Draw the cyclic phosphate linkage: Represent the phosphate group as a tetrahedral structure with one oxygen atom forming a bond with the 3'-hydroxyl group of ribose and another oxygen atom forming a bond with the 5'-hydroxyl group. This creates a cyclic structure.
Combine all components: Assemble the guanine base, ribose sugar, and cyclic phosphate group into a single structure. Ensure that the guanine is attached to the ribose at the 1' position and the cyclic phosphate is correctly linked to the 3' and 5' positions of the ribose.
Double-check the structure: Verify that all bonds are correctly represented, the cyclic phosphate linkage is intact, and the overall structure matches the description of cyclic guanosine monophosphate (cGMP).
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
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 components: a nitrogenous base, a five-carbon sugar (ribose or deoxyribose), and one or more phosphate groups. In the case of cGMP, the nitrogenous base is guanine, the sugar is ribose, and it contains a single phosphate group. Understanding this structure is essential for drawing and identifying nucleotides.
Recommended video:
1:21
Naming Nucleosides and Nucleotides Concept 2
Cyclic Nucleotides
Cyclic nucleotides, such as cyclic guanosine monophosphate (cGMP), are formed when the phosphate group of a nucleotide bonds to the sugar's hydroxyl group, creating a cyclic structure. This cyclic formation is crucial for the function of cGMP as a signaling molecule in various biological processes, including vasodilation and neurotransmission.
Recommended video:
1:21Naming Nucleosides and Nucleotides Concept 2
Guanine and Its Derivatives
Guanine is one of the four primary nitrogenous bases found in nucleic acids, and it plays a significant role in the structure of nucleotides. In cGMP, guanine is attached to the ribose sugar, and its specific arrangement influences the nucleotide's properties and functions. Recognizing guanine's structure helps in accurately drawing cGMP and understanding its biological significance.
Recommended video:
Guided course
02:49Ammonia Derivatives
Related Practice
Textbook Question
Draw the structure of a four-residue segment of DNA with the following sequence. (3′end) G-T-A-C (5′ end)
107
views
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.
1940
views
Textbook Question
Draw the structures of the following nucleotides.
(b) deoxycytidine monophosphate (dCMP)
939
views