P13.5: The biosynthetic pathway for the antibiotic compound rabelomycin begins with the condensation of malonyl CoA and acetyl CoA. Predict the product of this reaction, and propose a likely mechanism. (Org. Lett. 2010 12, 2814.) ? ? ΘΟ malonyl CoA SCOA + COAS CH3 acetyl CoA CO2 HSCOA
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- The dynamic process by which both forms of a- and B-D-glucopyranose in solution change slowly into an equilibrium mixture of both is known as (choose the name). OH OH Но но НО HO OH OH OH OH a-D-glucopyranose 36% B-D-glucopyranose 64% OA Acetylation O B. Enediol Rearrangement OC Mutarotation O D. Acetal Formation O E EpimerizationIf a solution of compound X is ncubated with a catalytic anount of enzyme Y the sucrose is trarsformed to glucose aid Euctose in the reaction 1X 1 fedose3 ghacose A eqahum, The concenttons of the seation comgoests he and 2mM glucose. What is Keg? Oa, 6 Ob4 Oa 20 O'd. 5 A Moving to another question wili save this response.6. Identifv each of the following reactions as an organic oxidation, reduction or neither. Pt + H, b. COO ÇO0 но -с — н C=0 Malate dehydrogenase CH; + NAD CH; + NADH + H COO COO Malate Oxaloacetate с. OH ACP + NADPH + H* ACP + NADP* d. OH + но
- c) Study the following reaction scheme for the preparation of a natural glycoside (compound 7) and answer the questions that follow: OH OAc Но excess Ac20 AcO pyridine, 0°C HO- Но. AcO- -OAc `0Ac HO Compound 3 Compound 4 HBr OCH3 OAc OAc AcO' AcO AcO AcO- OAc OAc Compound 6 Compound 5 Br NaOH, H2O OCH3 Он HO НО Compound 7 ii. Identify the unknown reagent(s) in the reaction scheme which converts compound 5 to compound 6.synthesis of suocybin NH₂ -OH L-Tryptophan, 7 OH NH2 NH2 PsiD -CO₂ Tryptamine, 6 (PsiH) [O] NH2 NH₂ OH -OH HO PsiD PsiK -CO₂ H 4-hydroxy- ATP ADP H tryptamine, 8 Norbaeocystin, 9 H 4-hydroxy-L- Tryptophan, 11 SAM PsiM) SAH HN OH O=P. O=P-O HO PsiM PsiK OH ADP ATP Psilocin, 2 SAH SAM Psilocybin, 1 Baeocystin, 10One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.
- Raloxifene is a drug used in the treatment of osteoporosis in postmenopausal women and those on glucocorticoids. In a study conducted by Izgelov et al. (2018), the two metabolites derived from raloxifene are shown and their intestinal metabolism are discussed. он Raloxifene 6-Glucuronide HO Raloxifene onge HQ. OH OH OH Raloxifene 4'-Glucuronide Determine the isomer configuration of the labelled double bond (shown in red) from the structure of raloxifene by writing the letter of the configuration in the provided box below. STRICTLY write the letter only.D-glucose can form two isomers of glucosides after reaction with methanol in presence of catalytic HCI as shown below. Suggest a mechanism for the following reaction. CH2OH CH,OH CH2OH HO CH;OH но HO но но. но OCH3 HČI HO. OH ÓCH3 OH онAn enzyme catalyzes each reaction given below. Which group does each enzyme belong to? а. pyruvate +NADH + H* → lactate + NAD* но. он он b. ethyl 2-methyl-5-thien-2-ylpentanoate + H2O → 2-methyl-5-thien-2-ylpentanoic acid + ethanol OH но
- ACTIVITY-4. Refer to the structures below. Draw the Haworth formula (pyranose) -OH но H- FOH FOH- но но H- H FOH H FOH- H- CH2OH CH2OH Alpha-D- glucopyranose Beta-D-glucopyranose (Haworth) Beta-D-glucopyranose Alpha-D- glucopyranose (Haworth) ACTIVITY-5. Draw the Haworth formula for D-mannose and D-galactose. Label the alpha and beta anomer. CYCLIC FORMS OF FRUCTOSE D-fructose, a ketohexose sugar, can be presented using furanose and pyranose. Cyclic Fisher (furanose) 1 2OH Open chain Fisher Haworth formula (furanose) 1 CH2OH HOH,C- 1 2 F0 НО 3_H. ÇH2OH ÇH2OH но з—н 4 H- H но 2 H-4 HO- H- 5. OH 13 H-5 FOH 6 CH,OH 14 OH H. 6 CH2OH D-fructose Alpha form Alpha form Cyclic Fisher (pyranose) Haworth formula (pyranose) 1 HOH2C-2 3. 1 HO- CH2OH Но H. 5 он 2 H-4 HO- Но 4 OH 3 H-5 FHO- OH H-6 H Alpha form of D-fructose Alpha form of D-fructose ACTIVITY-6. Draw the Fisher and Haworth formula for beta-D-fructose (furanose and pyranose form). Label the beta furanose and beta pyranose.3. pwwr) The use of acetyl CoA in nucleophilic acyl substitution reactions is well known. Below we see an example of a phosphorylated derivative of glycerol undergoing such a procedure. The process, which is enzymatic, is shown. Your job is to draw the curved arrows for each step. H CoA H3C S-CoA CH3 CH3 H-S-CoA 2- ОРО 2- ОРОЗ 2- ОРОЗ1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.