Interpretation:
The possible mechanism for the formation of heterocyclic base on protected ribosylamine on the reaction with
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 A nucleoside consists of a nucleobase (also termed as nitrogenous base) and a five-carbon sugar (either ribose or deoxyribose).
舧 A
舧 In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or N1 of a pyrimidine.
舧 Examples of nucleosides include cytidine, uridine, adenosine, guanosine and thymidine.
舧 Sugar (ribose/deoxyribose) and nitrogenous bases are linked through N-glycosidic bonds.
舧 These glycosidic bonds are formed by condensation reaction of first carbon of sugar molecule with the nitrogen atom
舧 This particular glycosidic bond is stable in basic solutions, but readily hydrolyzes in the presence of acids.
舧 Uridine ribonucleoside can be synthesized by the reaction of protected ribosylamine with
Want to see the full answer?
Check out a sample textbook solutionChapter 25 Solutions
Organic Chemistry
- Devise a synthesis of the tripeptide sequence Phe Thr Lys using acid chloride below and N-methylmorpholine (NMM) for your coupling. Propose a detailed reaction mechanism for this step. You may use any readily available reagents/ protecting groups for your synthesis. In your answer you should clearly state the chosen reagents and how they are introduced and removed in your synthesis. Mechanistic details, for these steps are NOT required. Ph `NH2 NH NH `NH CO HO Phe Thr Lys `NMearrow_forwardWhat is the product/s when Asetone is allowed to react with KMno4, H2O, NaOH while being heated in the presence of HCl. is there any sereochemistry associated with this reactionarrow_forwardIdentify the class of polymer, based on functional groups, for the polymers in Problems 26.43 and 26.48.arrow_forward
- The reaction of ninhydrin with an -amino acid occurs in several steps (a) The first step is loss of water to give a triketone. Show the mechanism of the reaction and the structure of the triketone.(b) The second step is formation of an imine by reaction of the amino acid with the triketone. Show its structure. (c) The third step is a decarboxylation. Show the structure of the product and the mechanism of the decarboxylation reaction. (d) The fourth step is hydrolysis of an imine to yield an amine and an aldehyde. Show the structures of both products. (e) The final step is formation of the purple anion. Show the mechanism of the reactionarrow_forward22:43 10. Provide the following: the resonance structure of the intermediate that can resonate into the other intermediate that is given the product that results from the given resonance structure Specify which product is the kinetic product and which is the thermodynamic product . OH 50% H₂SO4 H~arrow_forwardThe stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages ofDNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine anddeoxyadenosine.arrow_forward
- 26. (i) Why is the ester formation of alcohols and acid chlorides done in a weakly basic solution like pyrmidine? (ii) Why is this setup not viable for alcohols and carboxylic acids to form esters? pyrimidine deprotonates the alcohol; the alkoxide ion forms pyrimidine deprotonates the alcohol; the carboxylate ion forms pyrimidine deprotonates the tetrahedral intermediate; the alkoxide ion forms pyrimidine deprotonates the tetrahedral intermediate; the carboxylate ion formsarrow_forwardShow how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) Cyclobutyl methyl ketonearrow_forward22.55 (d only)arrow_forward
- The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardShow how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) 4-Phenyl-2-butanonearrow_forwardPropose a mechanism for the acid-catalyzed reaction of salicylic acid with aceticanhydride.(b) Explain why a single drop of sulfuric acid dramatically increases the reaction ratearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning