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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- rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…Acetolactate synthase transfers the acyl group of pyruvate to alpha-ketobutyrate. This is the first step in the biosynthesis of the amino acid isoleucine. Propose a mechanism for this reaction.Mechanism?
- If 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.Give typed full explanationc) 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.9
- Triose phosphate isomerase catalyzes the conversion of dihydroxyacetone phosphate (DHAP) into glyceraldehyde-3-phosphate (G3P). Which of the following illustrates this chemical reaction? a) A b) B c) C d) D4) 4- Customized synthesis of carbohydrate compounds is a popular area of research. Complete the following steps, as required, from a recent report, which begins with a (D)-glucopyranose. но HO Ph Ph HO OH A HO C. ÓCH3 HO HO HO HO 4. OH HOYH hosTH OCH3 OCH3 4. 4. NABH;CN HCI 1 equivalent of TsCl /py 1. CI -C. CI DMSO Ph OH 2) (CH3CH2);N Ph OCH3 (Swern reaction) 4. 4. NaN3 NaBH4 HO HƆ stereoselective formationof an isomer of compound F 4.Q13: For the following reactions indicate whether the reaction involves a cofactor or coenzyme? A В COA HN CH2OPO3 *H,N NH2 CH2OPO CH,OH ATP AMP NH2 CoA P. Glutamine CoA H Mg2+ н но он OH H OH Phosphohexose 12 но isomerase 3 Phenylacetate (excess supplied) Phenylacetyl CoA OH H Phenylacetylglutamine (excreted) Glucose 6-phosphate Fructose 6-phosphate AGº= 1.7 kJ/mol