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…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.One 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.
- 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.© Macmillan Learning 95 DEC H h Glycolysis intermediate Other compound 2- H-C-O-PO3 C=O HO-C-H H HO. -CH2 OH OH M Answer Bank a five-carbon phosphorylated compound Coo CH₂ MacBook Pro fructose Resources 203PO, -20₂ PO-CH₂ H₂C-OPO O-OH OH OH A 00 Σ
- #4The following sugar is? -ОН Но ОН O Но 0 ОН O A reducing sugar O Linked by an N-glycosidic bond O Derived from 2 ketoses O A non-reducing sugar trisaccharide -ОН НО ОН3. 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- ОРОЗ